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| 2C-B |
2C-B
2C-B is a psychedelic hallucinogenic drug first synthesized by Alexander Shulgin in 1974, sometimes used as an entheogen. The full name of the chemical is 4-bromo-2,5-dimethoxyphenethylamine. In his book PIHKAL (Phenethylamines I Have Known and Loved), Shulgin lists the dosage range as 16 to 24 mg. 2C-B is a white powder usually found in pressed tablets or gel caps, and is almost always taken orally. Snorting is also an effective though extremely painful way to ingest the drug, and will affect the body more quickly.
On December 20, 1994, in a notice of proposed rulemaking published in the Federal Register (59 FR 65521) and after a review of relevant data, the Deputy Administrator of the DEA proposed to place 4-bromo-2,5-DMPEA into Schedule I making 2C-B illegal in the United States. This became permanent law July, 2 1995. Prior to this, 2C-B was commercially available as an aphrodisiac under the tradename "Eros" which was manufactured by the German phamaceutical company Drittewelle. Recently 2C-B has been distributed under the street name "Nexus." In the past 2C-B has also been distributed as "Eve", "Venus", "Bees", and (incorrectly) "bromo-mescaline." Internationally, 2C-B is a Schedule II drug under the Convention on Psychotropic Substances[http://www.incb.org/pdf/e/list/green.pdf].
Not much information is known about the toxicity of 2C-B. Because 2C-B lacks an alpha-methyl group it is not considered an amphetamine such as MDMA, MDA, methamphetamine, or fenfluramine. 2C-B does not seem to deplete the brain of serotonin, and this suggests that it may not share the neurotoxic mechanisms of many amphetamines.
There are no known deaths caused by 2C-B, despite widespread use and relatively large overdoses (see the PIHKAL entry linked to on the bottom of this page), suggesting that the acute physical danger is relatively small. However, few (if any) proper studies have been conducted on its safety, physically or psychologically.
At lower doses 2C-B produces an entactogenic effect, but at higher doses the drug can produce intense visual and auditory effects, combined with everything from paranoia to euphoria, which is a good reason to not take high doses of 2C-B unless in a safe environment. Experience also tells us that persons with certain psychological disorders (such as schizophrenia) should be especially careful when using psychedelic drugs.
Recreationally it is often used with MDMA (Ecstacy).
Synthesized from 2-5-dimethoxy benzaldehyde. There is an alternate synthesis that starts with anise oil, thus making is easy for a semi-novice chemist to synthesize it.
See also
- Phenethylamine
External links
- [http://www.erowid.org/library/books_online/pihkal/pihkal020.shtml 2C-B Entry in PIHKAL]
- [http://www.erowid.org/chemicals/2cb/2cb.shtml Erowid 2C-B vault, includes reports from users of 2C-B, as well as scientific and government reports]
- [http://www.tacethno.com/info/2cb/2cbhistory.html 2C-B History]
Categorization
Category:Entactogens and Empathogens
Category:Psychedelic phenethylamines
Molecular massThe molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12).
The molecular mass can be calculated as the sum of the atomic masses of all the atoms of any one molecule. The molecular mass can also be measured directly using mass spectrometry. In mass spectrometry, the molecular mass of a small molecule (< ~200 atoms of a given element) is exact, that is, the sum of the most common isotopes of each element. Of larger molecules, it is average, or calculated using the elemental mass number or the periodic table, since there is likely to be a statistical distribution of atoms representing the isotopes throughout the molecule.
The molar mass of a substance is numerically equal to the molecular mass, but expressed in mass units per mole, usually as g/mol (grams per mole).
: Example:
: The atomic mass of hydrogen is 1.00784 u and that of oxygen is 15.9994 u; therefore, the molecular mass of water with formula H2O is (2 × 1.00784 u) + 15.9994 u = 18.01508 u. Therefore, one mole of water weighs 18.01508 grams. However, the exact mass of hydrogen-1 (the most common isotope) is 1.00783, and the exact mass of oxygen-16 (the most common isotope) is 15.9949, so the mass of the most common single molecule of water is 18.0105 u.
Molecular mass or molar mass are used in stoichiometry calculations.
Since molecules are created by chemical reactions, not nuclear reactions, a molecule's molecular mass exactly equals the sum of the atomic masses of its constituent atoms.
The gram-molecular weight is the molecular weight of a chemical compound expressed in grams. Thus the molecular weight of calcium carbonate is 100 therefore the gram-molecular weight is 100 g. The Gram Molecular Weight is frequently used, particularly for calculating the concentration of solutions. Thus a molar solution will contain the gram molecular weight of a chemical dissolved to produce one litre of solution.
Molecular mass in polymer Chemistry
In polymer chemistry, due to the varying chain lengths between the polymer macromolecules, various types of molecular mass are used to quantify the molar mass distribution.
See also
- Avogadro's number
- Atomic mass unit
- Dalton (unit)
External links
- [http://www.vias.org/simulations/simusoft_molform.html Learning by Simulations] Calculation of Molecular Formulas from Molecular Masses
Category:Mass
Category:Chemical properties
ja:分子量
Melting pointThe melting point of a solid is the temperature at which it changes state from solid to liquid. When considered as the temperature of the reverse change from liquid to solid, it is referred to as the freezing point.
For most substances, melting and freezing points are equal. For example, the melting point and freezing point of the element mercury is 234.32 kelvins (−38.83 °C or −37.89 °F). However, certain substances possess differing solid-liquid transition temperatures. For example, agar melts at 85 °C (185 °F) and solidifies from 32 to 40 °C (89.6 to 104 °F); this phenomenon is known as hysteresis.
Certain materials, such as glass, may harden without crystalizing; this is called an amorphous solid.
Unlike the boiling point, the melting point is relatively insensitive to pressure.
The material with the highest known melting point at atmospheric pressure is graphite, with a melting point of 3,948 kelvins (3,674.8 °C or 6,646.5 °F).
Water's Melting/Freezing point is 0 C, or 32 F.
Melting point is often used to ascertain purity of and characterise organic compounds. The melting point of a pure substance is always higher than the melting point of an impure sample of that particular substance. When two chemical substances are mixed, the melting point of the resultant mixture will be lower than the melting point of either constituent. The mixing ratio that results in the lowest possible melting point is known as the eutectic point.
See also
- phases of matter
- triple point
- Freezing-point depression
- Boiling Point
Category:Chemical properties
ko:녹는점
ja:融点
th:จุดหลอมเหลว
HydrochlorideIn chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines).
For example, reaction of pyridine (C5H5N) with hydrochloric acid (HCl) yields pyridine hydrochloride (C5H5N.HCl). Even though this style of formulas is often used for denoting the hydrochlorides, the dot incorrectly implies that the two molecules are weakly bonded together. It is the salt C5H5NH+ Cl- with correct chemical name pyridinium chloride.
Uses:
Converting otherwise insoluble amines into hydrochlorides is a common way to make them water and acid-soluble; ideal as they are most prevalent in oral medications. Many pharmaceutical substances used are prepared as hydrochlorides for just these reasons. The typical breadth of time needed for a hydrochloride to be absorbed is 15-30 minutes.
Examples of what they are medically used for are ubiquitous ranging from over the counter sinus relief to investigational radiotherapy antinausea meds (Zofran, Ondanestron Hydrochloride).
Category:Salts
Acetate:For the plastic material formerly used for photographic film, see Cellulose acetate.
Acetate, or ethanoate, is the anion of a salt or ester of acetic acid.
The acetate ion has the formula CH3COO-, and is the conjugate base of acetic acid.
Acetate can also refer to cellulose acetate, especially fibers or other derived products such as the acetate disc used in audio record production. Acetate can be found in many household products.
Historically (prior to the discovery and naming of actinium) the abbreviation Ac (or AC) was sometimes used in chemical formulas to indicate the acetate ion. For example, the formula for sodium acetate might be given as "NaAc", rather than the more modern "CH3COONa" or "NaC2H3O2". In the field of organic chemistry the abbreviation Ac refers to the acetyl group, therefore in the organic chemistry literature acetate is referred to as −OAc, sodium acetate as NaOAc, and ethyl acetate as EtOAc.
see also acetylation
Category:Carboxylate anions
CAS registry numberCAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
Chemical Abstracts Service (CAS), a division of the American Chemical Society, assigns these identifiers to every chemical that has been described in the literature. The intention is to make database searches more convenient, as chemicals often have many names. Almost all molecule databases today allow searching by CAS number.
As of Dec 4, 2005, there were 27,028,944 substances in the CAS registry — the current number is published [http://www.cas.org/cgi-bin/regreport.pl here].
About 4,000 new numbers are added each day.
CAS also maintains and sells a database of these chemicals, known as the CAS registry.
Format
A CAS registry number is separated by hyphens into three parts, the first consisting of up to 6 digits, the second consisting of two digits, and the third consisting of a single digit serving as a check digit. The numbers are assigned in increasing order and do not have any inherent meaning.
The checksum is calculated by taking the last digit times 1, the next digit times 2, the next digit times 3 etc., adding all these up and computing the sum modulo 10. For example, the CAS number of water is 7732-18-5, and the checksum is calculated as (8×1 + 1×2 + 2×3 + 3×4 + 7×5 + 7×6) mod 10 = 105 mod 10 = 5.
Isomers, enzymes, and mixtures
Different isomers of a molecule receive different CAS numbers: D-glucose has 50-99-7, L-glucose has 921-60-8, α-D-glucose has 26655-34-5, etc. Occasionally, whole classes of molecules receive a single CAS number: the group of alcohol dehydrogenases has 9031-72-5. An example of a mixture with a CAS number is mustard oil (8007-40-7).
Searches
When using CAS numbers for database searches, it is useful to include the numbers of closely related compounds. For instance, to search for information about cocaine (CAS 50-36-2), one should include cocaine hydrochloride (CAS 53-21-4), since that is the most common form of cocaine when used as a drug.
See also
- EC number (Enzyme Commission)
- EC# (EINECS and ELINCS)
- International Chemical Identifier (InChI)
- NSC number
- PubChem
- SMILES
- UN number
- Chemical database
External links
- [http://www.cas.org/EO/regsys.html CAS registry description], by the Chemical Abstracts Service
To find the CAS number of a compound given its name, formula or structure, the following free resources can be used:
- [http://pubchem.ncbi.nlm.nih.gov PubChem]
- [http://chem2.sis.nlm.nih.gov/chemidplus/chemidlite.jsp NIH ChemIDplus]
- [http://webbook.nist.gov/chemistry/ NIST Chemistry WebBook]
- [http://cactvs.cit.nih.gov/ NCI Database Browser]
- [http://chemfinder.cambridgesoft.com/ Chemfinder]
- [http://ecb.jrc.it/esis/esis.php European chemical Substances Information System (ESIS)] - useful for finding EC#
Category:Chemical numbering schemes
ja:CAS登録番号
Hallucinogenic drug:"Hallucinogen" redirects here. For the psychedelic trance project of Simon Posford, see Hallucinogen (musician).
Certain drugs can affect the subjective qualities of perception, thought or emotion, resulting in altered interpretations of sensory input, alternate states of consciousness, or hallucinations. This general group of pharmacological agents can be divided into three broad categories: psychedelics, dissociatives and deliriants. All of these agents act as neurotransmitter mimics, often as agonists or antagonists at neurotransmitter receptors. Their primary effects are markedly different from those of stimulants like cocaine or amphetamines, although most do have stimulating effects.
The term hallucinogen is often broadly applied, especially in current scientific literature, to some or all of these substances. The term is attracting increasing criticism, however, for being ethnocentric, dependent upon too broad a definition of hallucination, and implying that certain symptoms that are actually only associated with some substances are applicable to all of them. In all but a tiny minority of psychedelics, dissociatives, and deliriants, hallucinations of various kinds are only one of many effects produced. The nature of the hallucinations produced is dependant on the specific compound. Broadly speaking, psychedelics more often have various visually distorting effects, deliriants are a class of drug that commonly cause extremely strong, often overpowering and unwanted visual and auditory hallucinations.
These substances have a millennial history of traditional use in medicine and religion, where they have been prized for their perceived ability to enhance certain abilities and promote physical and mental healing. Together with other plant agents, like tobacco, they are thought to be the primary tools of shamans and other hierophants. Native American practitioners using peyote have reported success against alcoholism, and Mazatec practitioners routinely use psilocybin mushrooms for healing and divination.
Psychedelics
:Main article: psychedelic drug
The psychedelic (mind manifesting) drugs are classified as those whose primary action is that of enhancing or amplifying the thought processes of the brain typically through the disabling of filters which block or suppress unimportant or undesired signals to the conscious mind from other parts of the brain, including but not limited to the senses, emotions, memories and the unconscious (or subconscious) mind. This effect is sometimes referred to as mind expanding, or consciousness expanding as the conscious mind becomes aware of (or sometimes assaulted by) things normally inaccessible to it. At high levels this can become very overwhelming, and can result in achieving a dissociative state.
Classic psychedelics include LSD (acid), psilocybin (magic mushrooms), mescaline (peyote), LSA (morning glory seeds) and also Ayahuasca (yage). Some of the synthetic "club drugs" such as MDMA (ecstasy), 2C-B (nexus), DOM (STP) and 5-MeO-DIPT (Foxy Methoxy) which have much more specific action to particular aspects of the psyche are also classed as psychedelics, as well as cannabis (marijuana).
Some psychedelics (namely LSD, psilocybin and cannabis) are extremely non-toxic, making it nearly impossible to physically overdose.
Dissociatives
:Main article: dissociative drug
A dissociative is a drug which reduces (or blocks) signals to the conscious mind from other parts of the brain, typically (but not necessarily, or limited to) the physical senses. Such a state of sensory deprivation can facilitate self exploration, hallucinations, and dreamlike states of mind which may resemble some psychedelic mindstates. Essentially similar states of mind can be reached via contrasting paths -- psychedelic or dissociative. That said, the entire experience, risks and benefits are markedly different.
The primary dissociatives are similar in action to PCP (angel dust) and include Ketamine (an anaesthetic), and DXM (the active ingredient in cough syrup). Also included are nitrous oxide, salvia divinorum, and muscimol from the amanita muscaria (fly agaric) mushroom.
Some dissociatives also have CNS depressant effects, thereby carrying similar risks as opioids to slowing breathing or heart rate to levels resulting in death (when using very high doses). This does not appear to be true in other cases, toxic effects do not appear to exist in the case of salvia divinorum, and the principal risk of nitrous oxide seems to be due to oxygen deprivation. Long term use of dissociative anesthetics such as PCP and Ketamine (and possibly DXM) have been suspected to cause Olney's lesions, though these lesions have never been demonstrated in primates to date.
Deliriants
:Main article: deliriant
The deliriants (or anticholinergics) are a special class of dissociative which are antagonists for the acetylcholine receptors (unlike muscimol which is an agonist of this receptor). Deliriants are considered to be true hallucinogens as users will have conversations with people who aren't there, or become angry with a 'person' mimicking their actions, not realizing it is their own reflection in a mirror (which could be dangerous if they became aggressive towards a glass mirror). Where the cholinergics like amanita muscaria have effects akin to lucid dreaming (where one is consciously aware they are dreaming), the anticholinergics have effects akin to sleepwalking (where one doesn't remember what transpired during the experience).
Included in this group are such plants as deadly nightshade, mandrake, henbane and datura, as well as a number of pharmaceutical drugs when taken in very high doses such as the antihistamine diphenhydramine (Benadryl) and the antiemetic dimenhydrinate (Dramamine or Gravol).
In addition to the danger of being far more "out of it" than with other drugs, and retaining a truly fragmented dissociation from regular consciousness without being immobilized, the anticholinergics are toxic, can cause death due to overdose, and also include a number of uncomfortable side effects. These side effects include dehydration and mydriasis.
Etymology and alternative terms
A variety of different, imprecise terms have also been used to refer to drugs of this type. One of the first terms used in English to describe these substances was "Phantastica", coined in 1928 by Louis Lewin in his ground-breaking monograph of the same name. The term was applied to plants that "bring about evident cerebral excitation in the form of hallucinations, illusions and visions ... followed by unconsciousness or other symptoms of altered cerebral functioning." Lewin complained that the word "does not cover all that I should wish it to convey", and indeed with the advent of the discovery of LSD and the widespread scientific experimentation with it and similar drugs, numerous supposedly improved terms were constructed, including hallucinogen, psychedelic, psychotomimetic, psycholytic, schizophrenogenic, cataleptogenic, mysticomimetic and psychodysleptic.
Of all the terms created, "hallucinogen", meaning roughly "generating delusions and false notions" (particularly in the form of sensory distortions), probably enjoys the most widespread and accepted usage. "Psychedelic", meaning "mind manifesting" and emphasizing the introspective potential of the drugs, and "entheogen", meaning "becoming divine within", are also widely used, particularly among those with positive attitudes towards their usage. In some cases, authors who otherwise use these terms have felt themselves pressured to use "hallucinogen" or "psychotomimetic" (or sometimes "psychomimetic", in either case meaning "mimicking psychosis") in scientific publications. The terms "empathogen" and "entactogen" (see Empathogen/Entactogen) are also applied to certain drugs (notably those similar to MDMA) that are also sometimes classed as hallucinogens.
The World Health Organization effectively endorses the "psychotomimetic" point of view, defining a hallucinogen as "a chemical agent that induces alterations in perception, thinking, and feeling which resemble those of the functional psychoses without producing the gross impairment of memory and orientation characteristic of the organic syndromes." It considers the term to be synonymous with "psychedelic" and "psychoactive drug." [http://www.who.int/substance_abuse/terminology/who_lexicon/en/]
History of use
Hallucinogenic drugs are among the oldest drugs used by humankind, as hallucinogens naturally occur in mushrooms, cacti, and various other plants. Whether the use of hallucinogens is encouraged, unregulated, regulated, or prohibited, and whether hallucinogens are used for recreational, medicinal, or spiritual purposes, varies from culture to culture and nation to nation. In most nations of the world, the possession of many hallucinogens, even those that are common in nature, is a crime punished by fines, imprisonment or in many countries, death. For some religious purposes, however, there are exceptions. For instance, though possession of peyote cactus is illegal for most purposes in the United States, American Courts have upheld the Constitutional right of Native Americans to grow and consume peyote.
Traditional religious and shamanic use (entheogens)
In human culture hallucinogens have historically most commonly been used in the setting of religious or shamanic rituals. In this context they are more precisely referred to as entheogens, and are used to facilitate healing, divination, communication with the spirits, and coming of age ceremonies. Evidence exists for the use of entheogens in prehistoric times, as well as in numerous ancient cultures, including the Ancient Egyptian, Mycenaean, Ancient Greek, Vedic, Maya, Inca and Aztec cultures. The rise of the Abrahamic religions (Judaism, Christianity and Islam) caused a decline of entheogen use in their area. Witness the destruction of the Eleusinian Mysteries, or the Great Witch Hunt of the Early Modern Age, in which practitioners of entheogenic rites in Western Europe were accused of associating with the Devil. Nevertheless, some (mainly tribal) cultures have survived this (ongoing) assault and still practise entheogen use. In others, non-religious hallucinogen use, while not exactly encouraged, is tolerated and not seen as uncommon. Present-day, historical and mythological aspects of entheogens are discussed in the entry entheogen.
Early scientific investigations
Although natural hallucinogenic drugs have been known to mankind for millennia, it was not until the early 20th century that they received extensive attention from Western science. Earlier beginnings include scientific studies of nitrous oxide in the late 18th century, and initial studies of the constituents of the peyote cactus in the late 19th century. Starting in 1927 with Kurt Beringer's Der Meskalinrausch (The Mescaline Intoxication), more intensive effort began to be focused on studies of psychoactive plants. Around the same time, Louis Lewin published his extensive survey of psychoactive plants, Phantastica (1928). Important developments in the years that followed included the re-discovery of Mexican magic mushrooms (in 1936 by Robert J. Weitlaner) and ololiuhqui (in 1939 by Richard Evans Schultes). Arguably the most important pre-World War II development was by Albert Hofmann's 1938 invention of the semi-synthetic drug LSD, which was later discovered to produce hallucinogenic effects, in 1943.
Hallucinogens after World War II
After World War II there was an explosion of interest in hallucinogenic drugs in psychiatry, owing mainly to the discovery of LSD. Interest in the drugs tended to focus on either the potential for psychotherapeutic applications of the drugs (see psychedelic psychotherapy), or on the use of hallucinogens to produce a "controlled psychosis", in order to understand psychotic disorders such as schizophrenia. Between the mid 1950s and the mid 1960s over 1000 scholarly articles were published on hallucinogen research. Hallucinogens were also researched in several countries for their potential as agents of chemical warfare. Most famously, several tragic incidents associated with the CIA's MK-ULTRA mind control research project have been the topic of media attention and lawsuits.
At the beginning of the 1950s, the existence of hallucinogenic drugs was virtually unknown among the general public of the West. However this soon changed as several influential figures were introduced to the hallucinogenic experience. Aldous Huxley's 1953 essay The Doors of Perception, describing his experiences with mescaline, and R. Gordon Wasson's 1957 Life magazine article (Seeking the Magic Mushroom) brought the topic into the public limelight. In the early 1960s countercultural icons such as Timothy Leary, Allen Ginsberg and Ken Kesey advocated the drugs for their psychedelic effects, and a large subculture of psychedelic drug users was spawned. Many people argue that psychedelic drugs played a major role in catalyzing the vast social changes initiated in the 1960s.
As a result of the growing popularity of LSD, and, some contend, establishment disdain for the hippies with whom it was heavily associated, LSD was banned in the United States in 1967.
Social status of hallucinogens
After the fading from public sight of many elements of the 1960s counterculture, hallucinogen use took a less visible but nevertheless persistent role in Western society 1970s and 1980s. In the 1990s and 2000s something of a revival of interest in the drugs has occurred. There are probably several important contributing factors to the resurgence. One is the rise of dance-based rave and trance culture, in which participants frequently employ drugs such as the entactogen MDMA, and to a lesser extent, other hallucinogenic drugs such as LSD, magic mushrooms and ketamine, as an aid to inducing ecstatic or trance states of consciousness. A second major contributing factor to the revival of interest in hallucinogenic drugs has been the advent of the Internet and World Wide Web. This has made information pertaining to drugs much more accessible to the general public, provided a platform for advocacy that was not previously available, and has enabled otherwise isolated interested parties to communicate and exchange information and experiences. Some well-known contemporary authors of topics relating to hallucinogens include Terence McKenna, Alexander Shulgin, Jonathan Ott and Rick Strassman.
Legal status
As of 2004, most hallucinogens are illegal in most Western countries. One notable exception to the current criminalization trend is in parts of Western Europe, especially in the Netherlands, where hallucinogenic mushrooms are considered to be so-called "soft drugs", along with cannabis. While the possession of soft drugs is technically illegal, the Dutch government has decided that using law enforcement to combat their use is largely a waste of resources. As a result, public "coffeeshops" in the Netherlands openly sell cannabis, and "smart shops" sell drugs like psilocybin mushrooms and ayahuasca for personal use (See Drug policy of the Netherlands).
Since the latter part of the twentieth century, this attitude has spread throughout Europe; many European countries no longer actively pursue anti-drug policies, and rarely enforce extant legal penalties for personal-use quantities of hallucinogenic drugs. This is especially true with mild hallucinogens such as cannabis, which is rapidly gaining acceptance in western Europe as a harmless and socially acceptable intoxicant, much as alcohol is considered throughout the West. Despite being scheduled as a controlled substance in the mid 1980s, ecstasy's popularity has been growing since that time in western Europe and in the United States.
Attitudes towards hallucinogens other than cannabis have been slower to change. Several attempts to change the law on the grounds of freedom of religion have been made. Some of these have been successful, for example the Native American Church in the United States, and Santo Daime in Brazil. Some people argue that a religious setting should not be necessary for the legitimacy of hallucinogenic drug use, and for this reason also criticize the euphemistic use of the term "entheogen". Non-religious reasons for the use of hallucinogens including spiritual, introspective, psychotherapeutic, recreational and even hedonistic motives, each subject to some degree of social disapproval, have all been defended as the legitimate exercising of civil liberties, including freedom of thought.
Pharmacology
Hallucinogens can be classified by quality of action, mechanisms of action, or by chemical structure. These classifications often correlate to some extent. The classification system below attempts to blend these three approaches in order to create a balanced and simple overview that is as clear and easy to grasp as possible.
Almost all hallucinogens contain nitrogen and are classified as alkaloids. THC and Salvinorin A are exceptions. Many hallucinogens often have chemical structures similar to those of human neurotransmitters, such as serotonin, and temporarily interfere with the action of neurotransmitters and/or receptor sites.
A classical classification is that of Lewin (Phantastica, 1928):
Class I Phantastica roughly correspond to the psychedelics, which is a more modern term usually used as synonym to "hallucinogen" by people with positive attitudes towards them. Here the term is used a bit differently to discriminate one particular class of hallucinogens which it seems to describe best. They typically have no sedative effects (sometimes the opposite) and there is usually a clearcut memory to their effects.
Class II Phantastica correspond to the other classes in this scheme. They tend to sedate in addition to their hallucinogenic properties and there often is an impaired memory trace after the effects wear off.
Pharmacological classes of hallucinogens
- Tryptamines
- Lysergamides
- Phenethylamines
- Substituted phenethylamines
- Substituted amphetamines
- Empathogens and/or Entactogens (serotonin releasers)
- Cannabinoids (CB-1 cannabinoid receptor agonists)
- NMDA receptor antagonists and sigma1 ligands
- Kappa opioid receptor agonists
- Inhalants
- Cholinergics
- Tropanes
- Antihistamines
Hallucinogenic plants, fungi, and animals
Among the most well-known hallucinogenic plants and fungi are:
Plants
Psychedelics
- Ayahuasca (contains DMT and an MAOI, commonly Banisteriopsis caapi with Psychotria viridis)
- Epená (Virola sp.) (contains 5-MeO-DMT and DMT)
- Hawaiian baby woodrose (Argyreia nervosa) (contains Ergine)
- Ololiuhqui/Coaxihuitl (Turbina/Rivea corymbosa) (contains Ergine)
- Tlitliltzin/Badoh Negro (Ipomoea violacea) (contains Ergine)
- Iboga (Tabernanthe iboga) (contains ibogaine)
Cacti psychedelics
- Peruvian Torch cactus (Trichocereus peruvianus) (contains mescaline)
- Peyote cactus (Lophophora williamsii) (contains mescaline)
- San Pedro cactus (Trichocereus pachanoi) (contains mescaline)
Quasi-psychedelics
- Cannabis (contains THC)
- Sinicuichi (Heimia salicifolia) (questioned hallucinogenic activity)
- Nutmeg (Myristica fragrans) (questioned hallucinogenic activity)
Dissociatives
- Iboga (Tabernanthe iboga) (contains ibogaine)
- Diviner's sage (Salvia divinorum) (contains salvinorin A)
Deliriants
- Deadly nightshade (Atropa belladonna) (contains tropane alkaloids)
- Floripondio (Brugmansia sp.) (contains tropane alkaloids)
- Henbane (Hyoscyamus niger) (contains tropane alkaloids)
- Mandrake (Mandragora sp.) (contains tropane alkaloids)
- Thorn Apple/Jimson Weed (Datura sp.) (contains tropane alkaloids)
Fungi
Psychedelics
- Psilocybe mushrooms (Psilocybe sp. and some Conocybe, Panaeolus and Stropharia) (contain psilocybin and psilocin)
- Ergot fungus (Claviceps purpurea) (not hallucinogenic in itself, but contains LSD precursors)
Dissociatives
- Fly Agaric mushroom (Amanita muscaria) (contains muscimol)
Animals
Psychedelics
- Psychoactive toads (Bufo alvarius) (contain 5-MeO-DMT and Bufotenine)
See also
- Empathogen
- Entactogen
- Entheogen
- Magic mushrooms
- Psychedelic
- Psychoactive or psychotropic
- Pharmacology
- Psychedelic psychotherapy
- Research chemicals
- Richard Evans Schultes and Albert Hofmann, Plants of the Gods
- Set and setting
- WikiPedia:WikiProject Psychedelics, Dissociatives and Deliriants
External links
- [http://www.erowid.org/ Erowid]
- [http://www.dextromethorphan.ws/ DXM Harm Reduction Project], exclusively about DXM.
- [http://www.coricidin.org/ Coricidin (Dextromethorphan + Chlorpheniramine Maleate) Harm Reduction], devoted exclusively to risks of Coricidin abuse.
- [http://www.psychedelic-library.org/grinspoo.htm Psychedelic Drugs in the Twentieth Century (Grinspoon)]
- [http://www.psychedelicjones.com/ PsychedelicJones] One man's experiences exploring psychedelic consiousness with magic mushrooms, salvia divinorum and other substances.
- [http://www.cognitiveliberty.org Center for Cognitive Liberty and Ethics]
- [http://www.spiritplants.org/ Spirit Plants]
- [http://www.plot55.com/growing/ Growing Entheogenic Plants (Plot55.com)]
- [http://www.shroomery.org/ The Shroomery] Detailed information about magic mushrooms including identification, cultivation and spores, psychedelic images, trip reports and an active community.
- [http://www.sci-con.org/editorials/20030603.html Science & Consciousness Review] - The Neurochemistry of Psychedelic Experience
Category:Psychedelics, dissociatives and deliriants
ms:Halusinogen
ja:幻覚剤
Entheogen
:This entry covers entheogens in the strict sense of the word (i.e. hallucinogenic drugs used in a religious or shamanic context). For general information about these substances and their use outside religious contexts, see hallucinogenic drug and psychedelic.
The word entheogen is a modern term derived from two Ancient Greek words, ἔνθεος (entheos) and γενέσθαι (genesthai). Entheos means literally "in God", more freely translated "inspired". The Greeks used it as a term of praise for poets and other artists. Genesthai means "to cause to be". So an entheogen is "that which causes (a person) to be in God". The translation "creating the divine within" that is sometimes given is not quite correct -- entheogen implies neither that something is created (as opposed to just perceiving something that is already there) nor that that which is experienced is within the user (as opposed to having independent existence).
In its strictest sense the term refers to a psychoactive substance (most often some plant matter) that occasions enlightening spiritual or mystical experience, within the parameters of a cult, in the original non-pejorative sense of cultus. In a broader sense, the word "entheogen" refers to artificial as well as natural substances that induce alterations of consciousness similar to those documented for ritual ingestion of traditional shamanic inebriants, even if it is used in a secular context.
Those opposed to entheogens often use the claim that "drug-induced" religious experiences are invalid because they are "just" a result of drug action on the nervous system. However, there is an enormous amount of evidence that certain drugs can facilitate the experience of states of consciousness that are then described by the experiencing subjects in words that are indistinguishable from many reports of religious experiences without drugs. In the Marsh Chapel Experiment, which was run under the supervision of Timothy Leary, volunteer graduate school divinity students from the Boston area, almost all reported profound religious experiences under the influence of psilocybin. (A brief video about the Marsh Chapel experiment can be viewed [http://www.yoism.org/?q=node/52 here.])
Terminology and uses of the word
The term "entheogen" was coined in 1979 by a group of ethnobotanists and scholars of mythology (Carl A. P. Ruck, Jeremy Bigwood, Danny Staples, Richard Evans Schultes, Jonathan Ott and R. Gordon Wasson). The term was coined as a replacement for the terms "hallucinogen" (popularized by Aldous Huxley's experiences with mescaline, published as The Doors of Perception in 1953) and "psychedelic" (a Greek neologism for "soul-revealing", coined by psychiatrist Humphry Osmond, who was quite surprised when the well-known author, Aldous Huxley, volunteered to be a subject in experiments Osmond was running on mescaline). Ruck et al. argued that the term "hallucinogen" was inappropriate due to its etymological relationship to words relating to delirium and insanity. The term "psychedelic" was also seen as problematic, due to the similarity in sound to words pertaining to psychosis and also due to the fact that it had become irreversibly associated with various connotations of 1960s pop culture.
The meanings of the term "entheogen" were formally defined by Ruck et al.:
:In a strict sense, only those vision-producing drugs that can be shown to have figured in shamanic or religious rites would be designated entheogens, but in a looser sense, the term could also be applied to other drugs, both natural and artificial, that induce alterations of consciousness similar to those documented for ritual ingestion of traditional entheogens.
Since 1979, when the term was proposed, its use has become widespread. In particular, the word fills a vacuum for those users of entheogens who feel that the term "hallucinogen", which remains common in medical, chemical and anthropological literature, denigrates their experience and the world view in which it is integrated. Use of the strict sense of the word has therefore arisen amongst religious entheogen users, and also amongst others who wish to practice spiritual or religious tolerance.
The use of the word "entheogen" in its broad sense as a synonym for "hallucinogenic drug" has attracted criticism on three grounds. On pragmatic grounds, the objection has been raised that the meaning of the strict sense of "entheogen", which is of specific value in discussing traditional, historical and mythological uses of entheogens in religious settings, is likely to be diluted by widespread, casual use of the term in the broader sense. Secondly, some people object to the misuse of the root theos (Greek: god) in the description of the use of hallucinogenic drugs in a non-religious context, and coupled with the climate of religious tolerance or pluralism that prevails in many present-day societies, the use of the root theos in a term describing non-religious drug use has also been criticised as a form of taboo deformation. Thirdly there are some substances that at least partially fulfil the definition of an entheogen that is given above, but are not hallucinogenic in the usual sense. One important example is the bread and wine of the Christian Eucharist.
Ideological objections to the broad use of the term often relate to the widespread existence of taboos surrounding psychoactive drugs, with both religious and secular justifications. The perception that the broad sense of the term "entheogen" is used as a euphemism by hallucinogenic drug-users bothers both critics and proponents of the secular use of hallucinogenic drugs. Critics frequently see the use of the term as an attempt to obscure what they perceive as illegitimate motivations and contexts of secular drug use. Some proponents also object to the term, arguing that the trend within their own subcultures and in the scientific literature towards the use of term "entheogen" as a synonym for "hallucinogen" devalues the positive uses of drugs in contexts that are secular but nevertheless, in their view, legitimate.
Use of entheogens
Naturally occurring entheogens such as Datura were, for the most part, discovered and used by older cultures, as part of their spiritual and religious life, as plants and agents which were respected, or in some cases revered. By contrast, artificial and modern entheogens, such as LSD, never had a tradition of religious use.
Currently entheogens are used in three principle ways: as part of established traditions and religions, secularly for personal spiritual development, and secularly in a manner similar to recreational drugs. A lesser use of entheogens for medical and therapeutic use is rarely pursued due to legislative and cultural objections.
:The remainder of this entry pertains to the use of entheogens in a religious context. See Also: hallucinogenic drug, psychedelic.
Entheogen-using cultures
The use of entheogens in human cultures is generally ubiquitous throughout recorded history, including Christian society if the Eucharist is counted, and including Islamic society if Sufi practices are counted. The number of entheogen-using cultures is therefore very large. Some of the instances better known to Western scholarship are discussed here.
Africa
The best-known entheogen-using culture of Africa is the Bwitists, who used a preparation of the root bark of Iboga (Tabernanthe iboga). A famous entheogen of ancient Egypt is the Blue Lotus (Nymphaea caerulea). There is evidence for the use of entheogenic mushrooms in Côte d'Ivoire (Samorini 1995). Numerous other examples of the use of plants in shamanic ritual in Africa are yet to be investigated by western science.
Americas
Entheogens have played a pivotal role in the spiritual practices of most American cultures for millennia. The first American entheogen to be subject to scientific analysis was the peyote cactus (Lophophora williamsii). Used traditionally by many cultures of what is now Mexico, its use spread to throughout North America in the 19th century, replacing the toxic entheogen Sophora secundiflora (mescal bean). Other well-known entheogens used by Mexican cultures include psilocybin mushrooms (known to the Aztecs under the Nahuatl name teonanacatl), the seeds of several morning glories (Nahuatl: tlitliltzin and ololiuhqui) and Salvia divinorum (Mazatec: Ska Pastora; Nahuatl: pipiltzintzintli). Indigenous peoples of South America employ a wide variety of entheogens. Better-known examples include ayahuasca (Banesteriopsis caapi plus admixtures), borrachero (Brugmansia spp), San Pedro (Trichocereus spp) and various tryptamine-bearing snuffs, for example Epená (Virola spp), Vilca and Yopo (Anadananthera spp). The familiar tobacco plant, when used uncured in large doses in shamanic contexts, also serves as an entheogen in South America.
Asia
The indigeneous peoples of Siberia (from whom the term shaman was appropriated) have used the Fly Agaric mushroom (Amanita muscaria) as an entheogen. The ancient inebriant Soma, mentioned often in the Vedas, may have been an entheogen. (In his 1967 book, Wasson argues that Soma was Fly Agaric. The active ingredient of Soma is now presumed to be ephedrine, an alkaloid with entheogenic properties derived from the soma plant, identified as Ephedra pachyclada.)
The Rig Veda, the first of the Vedas and the oldest known religious document, has many reverent references to the Soma sacrament, and has stories that tie the archetypal image of the serpent to Soma, which teaches man of the divine. This theme was arguably picked up by the author of Genesis to describe the fall of man. In the third chapter of Genesis, a fruit that teaches the knowledge of good and evil (a "plant teacher") was offered to Eve by the serpent.
In the broadest sense, this was also the first instance of a plant that teaches being recorded in the religious history of man. The idea of a "plant teacher" has since been a staple of indigenous shamanic lore worldwide, and is often acompanied (and even offered) by the serpent in said lore.
Europe
The use of entheogens (other than the Eucharist) in Europe was all but eliminated with the rise of post Roman Christianity and especially during the great Witch hunts of Early Modernity. European witches used various entheogens, including deadly nightshade (Atropa belladonna), mandrake (Mandragora officinarum) and henbane (Hyoscyamus niger). These plants were used, among other things, for the manufacture of "flying ointments". In Christian society, witches were commonly believed to fly through the air on broomsticks after using the ointment. Consequently, any association with these plants could have proven extremely dangerous and lead to one's execution as a practitioner of witchcraft.
Oceania
Indigenous Australians are generally supposed not to have used entheogens, although there is a strong barrier of secrecy surrounding Aboriginal shamanism, which has likely limited what has been told to outsiders. Natives of Papua New Guinea are known to use several species of entheogenic mushrooms (Psilocybe spp, Boletus manicus; Thomas). It has been suggested that the Maori of New Zealand used Maori Kava (Macropiper excelsum) as an entheogen (Bock 2000).
"Entheogen" in Classical mythology and cult
Although entheogens are taboo in Christian and Islamic societies, their ubiquity and prominence in the spiritual traditions of other cultures is unquestioned. The entheogen, "the spirit, for example, need not be chemical, as is the case with the ivy and the olive: and yet the god was felt to be within them; nor need its possession be considered something detrimental, like drugged, hallucinatory, or delusionary: but possibly instead an invitation to knowledge or whatever good the god's spirit had to offer." (Ruck and Staples)
Most of the well-known modern examples, such as peyote, Psilocybin and other psychoactive mushrooms and ololiuhqui, are from the native cultures of the Americas. However, it has also been suggested that entheogens played an important role in ancient Indo-European culture, for example by inclusion in the ritual preparations of the Soma, the "pressed juice" that is the subject of Book 9 of the Rig Veda. Soma was ritually prepared and drunk by priests and initiates and elicited a paean in the Rig Veda that embodies the nature of an entheogen:
:"Splendid by Law! declaring Law, truth speaking, truthful in thy works, Enouncing faith, King Soma!... O [Soma] Pavāmana, place me in that deathless, undecaying world wherein the light of heaven is set, and everlasting lustre shines.... Make me immortal in that realm where happiness and transports, where joy and felicities combine..."
The Kykeon that preceded initiation into the Eleusinian Mysteries is another entheogen, which was investigated (before the word was coined) by Carl Kerenyí, in Eleusis: Archetypal Image of Mother and Daughter. Other entheogens in the Ancient Near East and the Aegean include the poppy, Datura, the unidentified "lotus" eaten by the Lotus-Eaters in the Odyssey and narkissos.
According to Ruck, Eyan, and Staples, the familiar shamanic entheogen that the Indo-Europeans brought with them was knowledge of the wild Amanita mushroom. It could not be cultivated; thus it had to be found, which suited it to a nomadic lifestyle. When they reached the world of the Caucasus and the Aegean, the Indo-Europeans encountered wine, the entheogen of Dionysus, who brought it with him from his birthplace in the mythical Nysa, when he returned to claim his Olympian birthright. The Indo-European proto-Greeks "recognized it as the entheogen of Zeus, and their own traditions of shamanism, the Amanita and the 'pressed juice' of Soma — but better since no longer unpredictable and wild, the way it was found among the Hyperboreans: as befit their own assimilation of agrarian modes of life, the entheogen was now cultivable" (Ruck and Staples). Robert Graves, in his foreword to The Greek Myths, argues that the ambrosia of various pre-Hellenic tribes were amanita and possibly panaeolus mushrooms.
Amanita was divine food, according to Ruck and Staples, not something to be indulged in or sampled lightly, not something to be profaned. It was the food of the gods, their ambrosia, and it mediated between the two realms. It is said that Tantalus's crime was inviting commoners to share his ambrosia.
Even in cultures where they are acceptable, improper use of an entheogen, by the unauthorized or uninitiated, has led to disgrace, exile, and even death. The expulsion of Adam and Eve from the Garden of Eden can be understood as such a parable of an entheogen misused, for the fruit of the Tree of Knowledge by its very nature is clearly part of what is denoted by "entheogen" a point made clearly by the Elohim:
:"And the Lord God said, 'Behold, the man is become as one of us, to know good and evil: and now, lest he put forth his hand, and take also of the tree of life, and eat, and live for ever:'
:Therefore the Lord God sent him forth from the garden of Eden, to till the ground from whence he was taken.
:So he drove out the man; and he placed at the East of the garden of Eden cherubims and a flaming sword which turned every way, to keep the way of the tree of life."
:::Genesis 3:23-25.
Indeed the entheogen offers godlike powers in many Traditional tales, including immortality. The failure of Gilgamesh in retrieving the plant of immortality from beneath the waters teaches that the blissful state cannot be taken by force or guile: when Gilgamesh lay on the bank, exhausted from his heroic effort, the serpent came and ate the plant.
Another attempt at subverting the natural order is told in a (according to some) strangely metamorphosed myth, in which natural roles have been reversed to suit the Hellenic world-view. The Alexandrian Apollodorus relates how Gaia (spelled "Ge" in the following passage), Mother Earth herself, has supported the Titans in their battle with the Olympian intruders. The Giants have been defeated:
:"When Ge learned of this, she sought a drug that would prevent their destruction even by mortal hands. But Zeus barred the appearance of Eos (the Dawn), Selene (the Moon), and Helios (the Sun), and chopped up the drug himself before Ge could find it."
::::—Apollodorus 1.34-38.
Entheogens in literature
Consumption of the imaginary mushroom anochi as the entheogen underlying the creation of Christianity is the premise of Philip K. Dick's last novel, "The Transmigration of Timothy Archer".
References
- Carl Ruck and Danny Staples, The World of Classical Myth 1994. [http://www.csp.org/chrestomathy/world_of.html Introductory excerpts]
- Huston Smith, Cleansing the Doors of Perception: The Religious Significance of Entheogenic Plants and Chemicals, 2000, Tarcher/Putnam, ISBN 1-58542-034-4
- [http://www.eleusis.ws/en/articles/vel-avorio.shtml G. Samorini 1995 "Traditional use of psychoactive mushrooms in Ivory Coast (Côte d'Ivoire)?" in Eleusis 1 22-27]
- [http://www.eleusis.ws/en/articles/bock.shtml M. Bock 2000 "Maori kava (Macropiper excelsum)" in Eleusis n.s. vol 4]
- [http://www.shaman-australis.com/~benjamin-thomas/ Benjamin Thomas Ethnobotany & Anthropology Research Page]
- Plants of the Gods: Their Sacred, Healing and Hallucinogenic Powers by Richard Evans Schultes, Albert Hofmann, Christian Ratsch - ISBN 0892819790
External links
Entheogen websites
- [http://www.entheogen.com entheogen.com] Online community and information resource focusing on shamanic plants
- [http://www.entheogenreview.com entheogenreview.com] Quarterly publication serving as a clearinghouse for current data about the use of visionary plants and drugs.
- [http://www.csp.org/practices/entheogens Council on Spiritual Practices Entheogen Project]
- [http://www.plot55.com/growing/ Growing Entheogenic Plants (Plot55.com)]
- [http://www.plot55.com/usage/ Using Entheogenic Plants (Plot55.com)]
- [http://www.erowid.org/ The Vaults of Erowid]
- [http://www.lycaeum.org/ The Lycaeum]
- [http://www.entheology.net/ Entheology.net: A Free Exchange Site for Entheogenic Plants and Seeds]
- [http://www.spiritplants.org/ Spirit Plants Forums]
Other
- [http://jeremybigwood.net/JBsPUBS/JBScientific/Entheogens/index.htm C. A. P. Ruck, J. Bigwood, D. Staples, J. Ott & R. G. Wasson 1979 "Entheogens," in Journal of Psychedelic Drugs 11, p. 145ff]
- [http://www.users.fast.net/~szimhart/bolondgomba.htm Joseph Szimhart, "Bolond Gomba: speculation about a mushroom's relationship to Genesis, Soma, Jesus and Santa Claus"]
- Entheos: The Journal of Psychedelic Spirituality an interdisciplinary journal that debuted July 2001, linking anthropology, religious studies, art history, and history. [http://www.maps.org/news-letters/v12n1/12143rob.html Review of initial issues]
- [http://www.egodeath.com Ego Death and Self-Control Cybernetics]
- [http://releasethereality.com "Release The reality"] Web-Journal for Entheogenic Warriors
- [http://www.csse.ca/CJE/Articles/FullText/CJE27-4/CJE27-4-tupper.pdf Entheogens and Existential Intelligence: The Use of Plant Teachers as Cognitive Tools] Canadian Journal of Education (2002)
Category:Entheogens
Entheogen
PiHKAL
PiHKAL is a 1991 book by Dr. Alexander Shulgin and Ann Shulgin about psychedelic phenethylamines.
The full title of the book is Phenethylamines I Have Known And Loved: A Chemical Love Story (ISBN 0963009605). The book is widely regarded as a pioneering and much respected work on the subject.
The book is arranged in two parts. The first part is a fictionalized autobiography of the couple. The second part contains detailed synthesis instructions for over 200 psychedelic compounds (most of which Shulgin personally invented), including dosages, subjective experiences, and other commentary.
Shulgin's choices of synthesis procedures in the second half of the book are themselves perhaps a small act of subversion: While the reactions are beyond the ability of people with no chemistry education, they tend to emphasize techniques that do not require difficult to obtain chemicals. Notable among these are the use of aluminum amalgam as a reducing agent (an unusual but easy to obtain reagent) and detailed suggestions on legal plant sources of important drug precursors such as safrole.
Through PiHKAL (and later, TiHKAL) Shulgin sought to ensure that his discoveries would escape the limits of professional research labs and find their way to the public; a goal consistent with his stated beliefs that psychedelic drugs can be valuable tools for self-exploration. The MDMA ('ecstasy') synthesis published in PiHKAL remains one of the most common clandestine methods to this day.
The second part of PiHKAL is available through Erowid.
See also
- Phenethylamine
- TiHKAL, a 1997 sequel by the same authors, about tryptamines.
External link
- [http://www.erowid.org/library/books_online/pihkal/pihkal.shtml PiHKAL HTML Version]
Category:Psychedelics, dissociatives and deliriants
Category:Psychedelic phenethylamines
Category:1991 books
Category:Science books
Category:Controversial books
Amphetamine
Amphetamine, also known as speed, is a synthetic stimulant used to suppress the appetite, control weight, and treat disorders including narcolepsy and Attention-deficit hyperactivity disorder. It is also used recreationally and for performance enhancement. These (latter) uses are illegal in most countries.
Amphetamine
Amphetamine is a synthetic drug with strong stimulant effects. In the United States, it is most commonly used for treatment of attention deficit disorders and narcolepsy, but is also approved as a weight loss medication in certain cases of obesity. Within the armed forces only, it is also frequently prescribed as an anti-fatigue pill for pilots or other individuals in situations requiring vigilance and alertness. Amphetamine is also used illegally to take advantage of these effects.
The term amphetamine causes a certain amount of confusion because it is often used incorrectly. Loosely, amphetamine can describe other drugs with similar, stimulant effects, namely methamphetamine and methylphenidate. Chemists often use the term "amphetamine class" to describe chemicals that are structurally similar (and often similar in effect as well) to amphetamine--namely, chemicals with an ethyl backbone, terminal phenyl and amine groups, and a methyl group adjacent to the phenyl. A large number of chemicals fall into this category, including the club drug MDMA (Ecstasy) and methamphetamine. It is important to note that such an "amphetamine class" does not technically exist. Phamacodynamically, these drugs all fall under the umbrella of central nervous system stimulants; chemically, they are phenylethylamines. Amphetamine, for example, is methylated phenylethylamine, and methamphetamine is double methylated phenylethylamine.
Amphetamine traditionally comes in the salt-form amphetamine sulphate and is comprised of 50% l- and 50% d-amphetamine (where l- and d- refer to levo and dextro, the two optical orientations the amphetamine structure can have). In the United States, pharmaceutical products containing solely amphetamine (for example, Biphetamine) are no longer manufactured. Today, dextroamphetamine (d-amphetamine) sulphate the the predominant form of the drug used; it consists entirely of d-isomer amphetamine, which is acts in a slightly different way on the brain than does l-amphetamine. Attention disorders are often treated using Adderall or generic equivalent formulations of mixed amphetamine salts that contain both d/l-amphetamine and d-amphetamine in the sulfate and saccharate forms mixed to a final ratio of 3 parts d-amphetamine to 1 part l-amphetamine.
It was first synthesized in 1887 by the German Chemist L. Edeleano, who called it "phenylisopropylamine".
Medicinal use
The experimental medical use of amphetamines began in the 1920s. It was introduced in most of the world in the form of the pharmaceutical Benzedrine in the late 1920s. The drug was used by the militaries of several nations, especially the air forces, to fight fatigue and increase alertness among servicemen. After decades of reports of abuse, the FDA banned Benzedrine inhalers and limited amphetamines to prescription use in 1959, but illegal use became common.
Along with methylphenidate (Ritalin), amphetamine is one of the standard treatments for ADHD. Beneficial effects for ADHD can include improved impulse control, improved concentration, decreased sensory overstimulation and decreased irritability. These effects can be dramatic, particularly in young children. The ADHD medication Adderall is composed of a timed-release combination of four different amphetamine salts.
When used within the recommended doses, side effects like loss of appetite tend to decrease over time. However, amphetamines last longer in the body than methylphenidate (Ritalin Concerta), and tend to have stronger side effects on appetite and sleep.
Amphetamines are also a standard treatment for narcolepsy as well as other sleeping disorders. They are generally effective over long periods of time without producing addiction or physical dependence.
Amphetamines are sometimes used to augment anti-depressant therapy in treatment-resistant depression.
Medical use for weight loss is still approved in some countries, but is regarded as obsolete and dangerous in, for example, the United States.
Performance enhancing use
Amphetamines are usually not used by athletes in sports involving extreme cardiovascular efforts, as methamphetamine and amphetamine put a great deal of additional stress on the heart.
The United States Air Force uses amphetamines (Dexedrine) as stimulants for pilots, calling them "go-pills". After a mission, the Air Force issues a "no-go pill' (Ambien) to help the pilot sleep.
Amphetamines have been popular among some truck drivers, construction workers, and factory workers whose jobs require long or irregular shift work or automatic, repetitive tasks. It is for this reason that they are sometimes labeled a "redneck drug". They are also used by white collar workers trying to stay alert during long hours of multitasking, or by students hoping to improve their academic performance. There has also been at least one report of the coercive administration of amphetemines to cannery workers in Thailand, in order to enhance productivity (Seabrook, 1996).
However, the majority of cases of non-medicinal amphetamine use appear to be recreational in nature.
Effects of use
Amphetamines release stores of norepinephrine and dopamine from nerve endings by converting the respective molecular transporters into open channels. Amphetamine also releases stores of serotonin from synaptic vesicles. Like methylphenidate (Ritalin) amphetamines also prevent the monoamine transporters for dopamine and norepinephrine from recycling them (called reuptake inhibition) which leads to increased amounts of dopamine and norepinephrine in synaptic clefts.
These combined effects rapidly increases the concentrations of the respective neurotransmitters in the synaptic cleft, which promotes nerve impulse transmission in neurons that have those receptors.
Physiological effects
Short-term physiological effects include decreased appetite, increased stamina and physical energy, increased sexual drive/response, involuntary bodily movements, increased perspiration, hyperactivity, jitteriness, nausea, itchy, blotchy or greasy skin, increased heart rate, irregular heart rate, and headaches. Fatigue can often follow the dose's period of effectiveness.
Long-term abuse or overdose effects can include tremor, restlessness, changed sleep patterns, poor skin condition, hyperreflexia, tachypnea, gastrointestinal narrowing, and weakened immune system. Fatigue and depression can follow the excitement stage. Erectile dysfunction, heart problems, stroke, and liver, kidney and lung damage can result from prolonged use. When snorted, amphetamine can lead to a deterioration of the lining of the nostrils.
Short-term effects can include alertness, euphoria, increased concentration, rapid talking, increased confidence, increased social responsiveness, nystagmus (eye wiggles), hallucinations, and loss of REM sleep (dreaming) the night after use.
Long term psychological effects can include insomnia, mental states resembling schizophrenia, aggressiveness, addiction or dependence with accompanying withdrawal symptoms, irritability, confusion, and panic. Chronic and/or extensively continuous use can lead to amphetamine psychosis which causes delusions and paranoia, but this is uncommon when taken as prescribed.
Legal issues
Example 1: In the United Kingdom, amphetamines are regarded as Class B drugs. The maximum penalty for unauthorised possession is three months' imprisonment and a £2,500 fine.
Example 2: In the United States, amphetamine and methamphetamine are Schedule II controlled drugs, classified as a CNS (Central Nervous System) Stimulant. A Schedule II drug is classified as one that: has a high potential for abuse, has a currently accepted medical use and is used under severe restrictions, and has a high possibility of severe psychological and physiological dependence.
Internationally, amphetamine is a Schedule II drug under the Convention on Psychotropic Substances.
Books
Major League Baseball
On November 15, 2005, Major League Baseball and the Major League Baseball Player's Association agreed to stiffen penalties for steroid users, as well as to start banning amphetamines.
Penalties for use of amphetamines are as follows:
A 50-game suspension for the first failed test, a 100-game suspension for the second failed test, and a lifetime ban for the third failed test.
See also
- Stimulants
- Phenethylamines
- Dextroamphetamine (Dexedrine and part of Adderall)
- Methylphenidate (Ritalin, Concerta)
- Cathinone
- Methcathinone
- Ephedrine
- Attention Deficit Hyperactivity Disorder
- Psychoactive drug
- Clandestine chemistry
- Uncle Fester (author)
External links
- (D-form — dextroamphetamine)
- (L-form and D,L-forms)
- (L-form — Levamphetamine or L-amphetamine)
- [http://abcnews.go.com/sections/2020/DailyNews/2020_pilotpills021220.html USAF use of amphetamines]
- [http://www.erowid.org/chemicals/amphetamines/amphetamines.shtml Erowid - Amphetamines]
- [http://www.thegooddrugsguide.com/amphetamines/index.htm The Good Drugs Guide - Amphetamines]
- [http://leda.lycaeum.org/?ID=364 Lycaeum - Amphetamines]
- Srisurapanont et al, [http://www.update-software.com/abstracts/AB003022.htm Treatment for amphetamine dependence and abuse]
- [http://www.drugs.com/Amphetamine Drugs.com - Amphetamine]
- [http://www.apaic.org Asia & Pacific Amphetamine - Type Simulant Information Centre] - a very extensive information source mangaged by the United Nations Office on Drugs and Crime.
Notes
#
Category:Schedule II controlled substances
Category:Sympathomimetic amines
Category:Phenethylamines
Category:Stimulants
Category:Amphetamines
Category:Military drugs
ms:Amfetamina
ja:アンフェタミン
MDMA
MDMA (3,4-methylenedioxymethamphetamine), most commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the secretion of large amounts of serotonin as well as dopamine and noradrenaline in the brain, causing a general sense of openness, empathy, energy, euphoria, and well-being. Tactile sensations are enhanced for some users, making general physical contact with others more pleasurable, but contrary to popular mythology, it generally does not have aphrodisiac effects. Its ability to facilitate self-examination with reduced fear has proven useful in some therapeutic settings, leading to its 2001 approval by the United States FDA for testing in patients with post-traumatic stress disorder.
Acute dehydration is a risk among users who are highly physically active and forget to drink water, as the drug may mask one's normal sense of exhaustion and thirst. Also the opposite, "water intoxication" resulting in acute hyponatremia has been reported. By far the biggest danger comes from the fact that other, more dangerous chemicals (such as PMA, DXM or methamphetamine) are either added to ecstasy tablets, or more often simply sold as ecstasy. Long-term effects in humans are largely unknown and the subject of much controversy —particularly with regard to the risks of severe long-term depression as a result of a reduction in the natural production of serotonin.
MDMA is also known by many other street names, including Adam, Beans, Candy, Disco Biscuits, E, Eccies, Googs, Jack and Jills, MaDMAn, M&Ms, Mollies, Pills, Rolls, Scoobies, Smarties, Tabs, Vitamin E, Vitamin X, X, XTC, Yaotou (in East Asia) and Yokes.
History
A patent for MDMA was originally filed on Christmas eve 1912 by the German pharmaceutical company Merck, and granted two years later (to the day.) At the time, MDMA was not known to be a drug in its own right; rather, it was patented as an intermediate chemical used in the synthesis of a styptic (a drug intended to control bleeding from wounds.) Over half a century would pass before the first known ingestion of MDMA by humans.
Contrary to many rumours, the drug was never used as an appetite suppressant or as a stimulant for armed forces during wartime. (This was in fact methamphetamine.) The U.S. Army did, however, do lethal dose studies of it and several other compounds in the mid-1950's. It was given the name EA-1475, with the EA standing for Edgewood Arsenal. The results of these studies were not declassified until 1969. MDMA was first brought to public attention through Dr. Alexander Shulgin in the 1960s who recommended it for use in certain therapy sessions, naming the drug 'window' (he discovered it while searching for compounds that might have a similar psychoactive effect as other compounds contained in nutmeg). It was widely used therapeutically by US psychotherapists (especially on the West Coast) because of its empathogenic effects until its criminalization in the late 1980s. The drug was hailed as a miracle by therapists and counselors who claimed couples could have six months worth
of progress in one use of the drug, and soldiers returning from the Vietnam war could overcome their PTSD sometimes more effectively than talk or group therapy. A small number of therapists continue to use it in their practices today. (See below for 2001 FDA approval and DEA licensing for use in patients with post-traumatic stress disorder.)
Until 1985, MDMA was not illegal in the United States. Recreationally, it first came into prominence in certain trendy yuppie bars in the Dallas area, then in gay dance clubs. From there, use spread to rave clubs, and then to mainstream society. During the 1990s, along with the growing popularity of the rave subculture, MDMA use became increasingly popular among young adults in universities and later in high schools. It rapidly became one of the four most widely used illegal drugs in the US, along with cocaine, heroin and marijuana.
Chemistry
The chemical structure of MDMA is similar to those of mescaline and methamphetamine, but the phenyl ring is substituted with a methylenedioxy group in position 3,4.
It is a member of the phenethylamine family, a group of substances typically having pronounced biological activity.
MDMA is synthesized from MDP2P through a chemical reaction known as reductive amination. MDMA has a chiral center at the alpha carbon (next to the methylamino group).
Pharmacokinetics
MDMA has complex nonlinear pharmacokinetics, due MDMA's ability to inhibit CYP2D6. It is metabolised via N-demethylation to several active metabolites including MDA, although the conversion rate in humans is low. The metabolism is primarily by the cytochrome P450 enzymes CYP2D6 (in humans, but CYP2D1 in mice), and CYP3A4 . Large increases in blood and brain concentrations are mostly due to autoinhibition of CYP2D6 metabolism--if the user takes consecutive doses of the drug, disproportionately high plasma concentrations can result.
A significant quantity is excreted unchanged in the urine, especially when the drug is taken at higher doses.
Ecstasy as a recreational drug
The primary effects of MDMA include feelings of openness, euphoria, empathy, love, and heightened self-awareness. Its initial adoption by the dance club sub-culture is probably due to the enhancement of the overall social and musical experience. Taking MDMA or Ecstasy is commonly referred to as rolling, popping, dropping, pilling, flipping, getting off-tap, "eating skittles", dosing, thizzin.
MDMA use has increased markedly since the late 1980s and spread beyond its original sub-cultures to mainstream use. Prices have also fallen since its introduction, with an evening's drug use often costing less than an equivalent evening drinking alcohol, although street price can vary between as little as $5 to as much as $40 per tablet. This depends on the drug being bought beforehand or on the place of usage (which drastically increases price). In countries in which distribution is more extensive, such as in the Netherlands, prices can sometimes be as low as $1 per tablet. In Britain, a usual price is around £2.50 for a pill (although recent media reports as of September 2005 show the price dropping as low as 50p in many parts of the country), and £20 for a half gram of pure MDMA powder, although like any illegal substance the price varies wildly depending on how many hands it has passed through. In the U.S. the prices varies anywhere from 10$ a pill to 30$. In countries where distribution is more difficult prices are accordingly higher; for example in New Zealand prices start at around $30 NZD ($15 US) and can get as high as NZ $80.
Supply and administration
MDMA is usually ingested in pill form. Pills come in a variety of "brands", usually identified by the icons stamped on the pills. The brands never consistently designate the actual active compound within the pill, as anyone can make their own pills which copy the features of a well-known brand.
Pills sold illegally on the street don't always have MDMA as the only active ingredient. Black market pills most likely contain methamphetamine, but have been found to contain analogues such as MDEA, MDA and MBDB, and occasionally other unrelated psychoactive additives such as amphetamines (speed), DXM, ephedrine, PMA, caffeine, ketamine (Special K), and others.
ketamine
While overdose from MDMA itself is rare, many more toxic substances are often sold as ecstasy, and overdose or other adverse reaction to adulterants is not uncommon. MDMA appears to be one of the most commonly adulterated drugs.
Many legal pills such as aspirin, paracetamol (acetaminophen), or even canine heartworm tablets have had the letter E scratched into them and been sold as ecstasy, for enormous profit. (This is a minor plot device in the movie Go.) Such false labeling can have deadly results, as a significant number of people are allergic to aspirin. Paracetamol is fairly hepatotoxic and can cause significant liver damage or death if taken in large doses, as might happen to a person taking four or five tablets in quick succession, thinking the tablets to be ecstasy.
Although full and proper characterization of ecstasy pills requires advanced lab techniques such as Gas chromatography-mass spectrometry, it is also possible to use a less accurate presumptive alkaloid test known as the Marquis reagent. DanceSafe sells testing kits, and includes an extensive database of photographs of different pills, along with the results of a laboratory analysis of their contents. EcstasyData.org [http://www.ecstasydata.org/] is a non-profit site that tests the purity of street pills and compiles results. Most blackmarket pills are made in basement labs and are dangerous because of house hold chemicals near by.
Effects
Neurological effects
Serotonin is one of the chemicals responsible for mood and pleasure. MDMA's main action is believed to cause serotonin stores in the brain to release abnormally large quantities of serotonin into the synapses during the 4 to 6 hour high, which is responsible for the primary subjective effects. MDMA also raises dopamine and norepinephrine levels and promotes the release of the hormone prolactin. These effects are primarily due to MDMA's action on the monoamine transporters, SERT (serotonin transporter), DAT (dopamine transporter) and NET (norepinephrine transporter).
Other short-term effects
Apart from the dangers from impurities, the primary acute risks of taking MDMA are allergic reaction, which is extremely rare, and dehydration. Like many amphetamines, MDMA can mask the body's normal thirst and exhaustion responses, particularly if a user is dancing or is otherwise physically active for long periods of time without hydration. MDMA is known to temporarily reduce the body's ability to regulate its core temperature, and in high-temperature surroundings (e.g. clubs) combined with physical exertion this may lead to hyperpyrexia if precautions are not taken to remain cool. In sedentary therapeutic use, incidence of dehydration is not statistically significant. Experts do warn regular users of the drug in more physically active social settings to be cognizant of water intake. While dehydration is undesirable, there also have been a very small number of users overly concerned about hydration drinking excessive water and suffering from water intoxication and associated
hyponatremia (dilution of the blood that can cause swelling of the brain). This is what caused the death of British teen Leah Betts, which may be the world's most widely publicised MDMA-related fatality.
Some users also report decreased libido or impotence, although studies in this area have provided conflicting results [http://www.idmu.co.uk/esex.htm].
Long-term effects
Long-term effects are still unknown and heavily debated among scientists.
There are several reports of Hallucinogen Persisting Perception Disorder being induced by MDMA. In some cases, the disorder appears to be permanent. The disorder seems to occur in only a small percentage of users, and its mechanism of causation is unknown.
The central criticism of MDMA is the "what goes up must come down" theory, which deals with MDMA's artificial boosting of serotonin levels as causing the inverse effect of diminishing of the brain's natural production of serotonin — producing symptoms of acute or chronic depression. However while mood and serotonin levels are known to be related, its not yet clear by what chain of mechanisms serotonin causes changes in mood, and in turn, which effects can be linked to MDMA.
Some experiments indicate that continuous use at very high doses may lead to the synaptic terminals of serotonin neurons being damaged. The precise mechanism of this action is unknown, but recent evidence (Jones 2004; Miller 1997; Monks et al. 2004) suggests that the metabolic breakdown of MDMA includes the formation of reactive oxygen species (ROS), chemicals known to cause oxidative cell damage when taken up into the serotonin neurons.
This effect has been observed in the brains of rats, where the serotonin terminals of animals who are given extremely high doses of MDMA over a prolonged period of time (usually one to two orders of magnitude greater than a typical human dose) become withered and useless. This hypothesis is supported by the fact that the administration of selective serotonin reuptake inhibitors ("SSRIs", which bind to the serotonin cell's reuptake transporters and thus block ROS from entering the serotonin cells) along with or immediately following MDMA seems to completely block neuron damage in rats given MDMA.
For this reason many users self-administer an SSRI while, or shortly after taking MDMA, in an attempt to prevent possible neurotoxicity. These SSRIs are typically antidepressants such as Prozac or Zoloft. It should be noted, however, that MDMA use in conjunction with a different class of antidepressants, namely Monoamine oxidase inhibitors, is strongly contra-indicated due to danger of serotonin syndrome.
Many users also attempt to replenish the deficit of serotonin which follows the use of MDMA by administering 5-HTP. The serotonin precursor 5-HTP, which is commerically available as a dietary supplement, reportedly supplies the user with more of the raw materials to synthesize the neurotransmitter.
Because MDMA's neurotoxicity is known to be highly dependant on its metabolic disposition (Jones 2004; de la Torre & Farré 2004), it is not known whether experiments in rats and monkeys have any direct bearing on human users.
Considerable research has been done into possible cognitive-behavioral deficits among ecstasy users but data have been largely inconclusive. At least two meta-analyses of these studies have been completed (Morgan 2000; Sumnall & Cole 2005). Morgan's analysis of 17 studies showed that ecstasy users had a slight tendency to be more impulsive and depressed than controls. Sumnall and Cole's analysis showed a slight increase in the prevalence of depressive symptoms in ecstasy users over controls. Of course, in retrospective studies like these we are always faced with a chicken-or-egg question: did these impulsive and depressed people use ecstasy to self-medicate or did otherwise normal people become depressed and impulsive after using ecstasy? This question has not been answered. Moreover, such research is problematic as ecstasy users are much more likely than control subjects to have taken other drugs in addition to ecstasy. This makes it difficult for researchers to establish a direct causal relationship.
Although some experimental evidence exists indicating that long-term ecstasy users experience memory difficulties, a large study in 2002 (Strote et al.) showed that ecstasy users in 4-year colleges have GPAs which do not differ significantly from those of non-users.
According to one study, MDMA use has led to to rhabdomyolysis (muscle breakdown) as a consequence of MDMA-induced hyperpyrexia (abnormally high body temperature). Rhabdomyolysis can cause renal failure and death. T | | |
