3,4-Methylenedioxyamphetamine
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3,4-Methylenedioxyamphetamine
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| Systematic (IUPAC) name | |
| 1-(benzo[1,3]dioxol-5-yl)propan-2-amine | |
| Identifiers | |
| CAS number | ? 4764-17-4 51497-09-7 61614-60-6 65620-66-8 |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C10H13NO2 |
| Mol. mass | 179.22 g/mol |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | Hepatic, CYP extensively involved |
| Half life | dose dependent 6-10 hours |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US) |
| Routes | Sublingual |
3,4-Methylenedioxyamphetamine (MDA or Tenamfetamine) is a psychedelic hallucinogenic drug and empathogen/entactogen of the phenethylamine family. It is mainly used as; a recreational drug, an entheogen, and a tool in use to supplement various types of practices for transcendence, including in meditation, psychonautics, and illegal psychedelic psychotherapy, whether self administered or not. It was first synthesized by G. Mannish and W. Jacobson in 1910. There are about 20 different synthetic routes described in the literature for its preparation.
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[edit] Medical use
MDA was first used in animal tests in 1939, and human trials began in 1941 in the exploration of possible therapies for Parkinson's disease. From 1949 to 1957, more than 500 human subjects were given MDA in an investigation of its potential use as an antidepressant and/or anorectic by Smith, Kline, and French. The United States Army also experimented with the drug, code named EA-1298, while working to develop a truth drug or incapacitating agent. One human subject died in January 1953 after being intravenously injected with 500mg of the drug. MDA was patented as a cough suppressant by H. D. Brown in 1958, as an ataractic by Smith, Kline, and French in 1960, and as an anorectic under the trade name “Amphedoxamine” in 1961. Several researchers, including Claudio Naranjo, have explored MDA in the field of psychotherapy.
MDA is very similar to MDMA, but its hallucinogenic effects are more prominent than those of MDMA, and the powerful sense of empathy associated with MDMA is usually overpowered by mental and visual distortions caused by MDA. Although the feeling of empathy is still very noticeable, MDA is less predictable than MDMA and thus its effects can vary greatly from person to person. MDA can cause immense euphoria, but by different ways and means from MDMA.
[edit] Synthesis
One method of MDA synthesis, is to turn safrole into isosafrole via isomerization. The isosafrole is then oxidized, using a Wacker process or a peroxyacid, to produce MDP2P (methylenedioxyphenylacetone). Finally, it is converted to MDA via reductive amination of Ammonia. This synthesis is very similar to that of MDMA (Ecstasy) and of MDEA. The most common route is by starting from piperonal, and condensing it with nitroethane. The resulting nitrosafrole can then be reduced to MDA with a suitable reducing agent.
[edit] Recreational use
MDA began to appear on the recreational drug scene around 1963 to 1964. It was then inexpensive and readily available as a research chemical from several scientific supply houses. Although now illegal, MDA continues to be bought, sold, and used for recreational purposes, often in the form of tablets purporting to contain MDMA (Ecstasy).
[edit] Effects
A recreational dose of MDA is commonly between 80 and 160mg. The “R” optical isomer is more potent than the “S” optical isomer. Although there is some debate, the duration of the drug is now generally believed to be roughly 6 to 10 hours (In the late 90s, Alexander Shulgin changed his opinion of the duration to 3-6 hours). The effects of the drug are quite similar to those of MDMA (Ecstasy), including empathogen/entactogenic effects, though typically less intense than a similar dosage of MDMA[citation needed]. Because of these effects, MDA was called the "hug drug" and was alleged to stand for “Mellow Drug of America” in the 1960s. Most users feel that MDA has more psychedelic or hallucinogenic qualities than MDMA.
The LD50 in mice has been reported as 92mg/kg by intraperitoneal injection.
MDA differs from its methylated cousin MDMA in its toxicity, in that it is clearly more toxic, with toxicity indicative of overstimulation of the central nervous system.[1] Symptoms of acute toxicity may include agitation, sweating, increased blood pressure and heart rate, dramatic increase in body temperature, convulsions, and death. Death is usually caused by cardiac effects and hemorrhaging in the brain.[1] The website erowid.org lists the fatality rate at roughly 2 in 100,000 users.[2]
The experience is similar but has some distinct differences compared with MDMA. MDA causes the same kind of serotonin release as MDMA, leading to euphoria and its empathogen/entactogen effects. However, MDA has a higher affinity for 5-HT2A receptors, thus causing more psychedelic-like effects, such as hallucinations.
[edit] Legality
In 1970, the Controlled Substances Act was enacted in the United States, placing MDA into Schedule I. It is similarly controlled in other nations. In Canada MDA is a Schedule III drug. Internationally, MDA is a Schedule I drug under the Convention on Psychotropic Substances. The US has also essentially banned any drug with (methylenedioxy) in its structure, as well as several other phenethylamine-based compounds. This means that all unscheduled MDXX chemicals can be prosecuted under the Federal Analog Act [3]
[edit] See also
[edit] External links
[edit] References
- ^ a b Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.
- ^ Erowid.org
- ^ Incb.org
- Lee, M.A. and Shlain, B., Acid Dreams: The CIA, LSD, and the Sixties Rebellion. Grove, 1985.
- Stafford, P. Psychedelics Encyclopedia. Ronin, 1992.
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