МДА: Эмпатогендік әсері мен химиялық қасиеттері

Empathogen entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4 Methylenedioxyamphetamine (also known as MDA and sass) is an empathogen entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal. MDA is rarely sought as a recreational drug compared to other amphetamines; however, it remains widely used due to it being a primary metabolite, the product of hepatic N dealkylation, of MDMA (ecstasy). It is also a common adulterant of illicitly produced MDMA.

MDA currently has no accepted medical use.

MDA is bought, sold, and used as a recreational 'love drug', due to its enhancement of mood and empathy. A recreational dose of MDA is sometimes cited as being between 100 and 160 mg. thought to be activated by initial metabolism of MDA.

MDA is a substrate of the serotonin, norepinephrine, dopamine, and vesicular monoamine transporters, as well as a TAAR1 agonist, and for these reasons acts as a reuptake inhibitor and releasing agent of serotonin, norepinephrine, and dopamine (that is, it is an ). It is also an agonist of the serotonin 5 HT2A, 5 HT2B, and 5 HT2C receptors and shows affinity for the α2A , α2B , and α2C adrenergic receptors and serotonin 5 HT1A and 5 HT7 receptors. The (S) optical isomer of MDA is more potent than the (R) optical isomer as a psychostimulant, possessing greater affinity for the three monoamine transporters. In terms of the subjective and behavioral effects of MDA, it is thought that serotonin release is required for its empathogen entactogen effects, release of dopamine and norepinephrine is responsible for its psychostimulant effects, dopamine release is necessary for its euphoriant (rewarding and addictive) effects, and direct agonism of the serotonin 5 HT2A receptor is causative of its psychedelic effects.

The duration of the drug has been reported as about 6 to 8 hours.

MDA is a substituted methylenedioxylated phenethylamine and amphetamine derivative. In relation to other phenethylamines and amphetamines, it is the 3,4 methylenedioxy, α methyl derivative of β phenylethylamine, the 3,4 methylenedioxy derivative of amphetamine, and the N desmethyl derivative of MDMA.

MDA is typically synthesized from essential oils such as safrole or piperonal. Common approaches from these precursors include:
Reaction of safrole's alkene functional group with a halogen containing mineral acid followed by amine alkylation. Wacker oxidation of safrole to yield 3,4 methylenedioxyphenylpropan 2 one (MDP2P) followed by reductive amination or via reduction of its oxime. Henry reaction of piperonal with nitroethane followed by nitro compound reduction. Darzens reaction on heliotropin was also done by J. Elks, et al. This gives MDP2P, which was then subjected to a Leuckart reaction. Two dogs or dopeboy clandestine method synthezized from helional as starting material. First creation of oxime using hydoxylamine. Then beckman reaction with nickel acetate to form the amide. Then hoffman rearrangement to form the freebase amine. Then an acid base extraction.

MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross react significantly with MDA and major metabolites of MDMA, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.

MDA constitutes part of the core structure of the β adrenergic receptor agonist protokylol.

MDA was first synthesized by Carl Mannich and W. Jacobsohn in 1910. 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 five hundred human subjects were given MDA in an investigation of its potential use as an antidepressant and/or anorectic by Smith, Kline & French. The United States Army also experimented with the drug, code named EA 1298, while working to develop a truth drug or incapacitating agent. Harold Blauer died in January 1953 after being intravenously injected, without his knowledge or consent, with 450 mg of the drug as part of Project MKUltra. MDA was patented as an ataractic by Smith, Kline & French in 1960, and as an anorectic under the trade name "Amphedoxamine" in 1961. 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. Several researchers, including Claudio Naranjo and Richard Yensen, have explored MDA in the field of psychotherapy.

When MDA was under development as a potential pharmaceutical drug, it was given the international nonproprietary name (INN) of tenamfetamine.

MDA is schedule 9 prohibited substance under the Poisons Standards. A schedule 9 substance is listed as a "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities."