Methylenedioxyamphetamine

"Methylenedioxyamphetamine" redirects here. It is not to be confused with MDMA (methylenedioxymethamphetamine).

Tenamfetamine (INN)

Systematic (IUPAC) name
(R) 1-(benzo[1,3]dioxol-5-yl)propan-2-amine
Clinical data
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Schedule I UN: Psychotropic Schedule I
Routes of administration	Oral, Sublingual, Insufflation
Pharmacokinetic data
Metabolism	Hepatic, CYP extensively involved
Excretion	Renal
Identifiers
CAS Number	4764-17-4 Y
ATC code	None
PubChem	CID: 1614
DrugBank	DB01509 Y
ChemSpider	1555 Y
UNII	XJZ28FJ27W Y
ChEMBL	CHEMBL6731 Y
Chemical data
Formula	C10H13NO2
Molecular mass	179.22 g/mol
SMILES NC(C)CC1=CC2=C(C=C1)OCO2
InChI InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3 Y Key:NGBBVGZWCFBOGO-UHFFFAOYSA-N Y
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Methylenedioxyamphetamine, also known as 3,4-methylenedioxy-amphetamine, MDA, tenamfetamine (INN), or colloquially as "Sally", "Sass", or "Sass-a-frass", is a psychoactive drug of the substituted methylenedioxyphenethylamine and substituted amphetamine classes of drugs that is consumed primarily for its entactogenic, psychedelic, and psychostimulant effects. Pharmacologically, MDA acts as a serotonin-norepinephrine-dopamine releasing agent and reuptake inhibitor. Possession of MDA is illegal in most countries. Some limited exceptions exist for scientific and medical research. The recreational use of MDA predates its more widely used analog MDMA (ecstasy).

Use

Medical

MDA currently has no accepted medical use.

Recreational

Although illegal, MDA is bought, sold, and used as a recreational 'love drug', due to its enhancement of empathy. A recreational dose of MDA is commonly between 100 and 160 mg.

Effects

While MDA is generally similar to MDMA, users report that MDA has more stimulant and psychedelic qualities and less intense entactogenic effects than MDMA. MDA is also considered less predictable than MDMA, with effects varying greatly from person to person. MDA is best known for its enhancement of the experiences of dancing and sex.

Overdose

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 subsequent hemorrhaging in the brain (stroke).

Pharmacology

Pharmacodynamics

MDA is a substrate of the serotonin, norepinephrine, and dopamine transporters, as well as a TAAR1 agonist, and for that reason, acts as a reuptake inhibitor and releasing agent of serotonin, norepinephrine, and dopamine (or as an SNDRA). It is also an agonist of the 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors, and shows affinity for the α_2A-, α_2B-, α_2C-adrenergic receptors and 5-HT_1A and 5-HT₇ receptors.

The effect on serotonin may explain the similar euphoric and empathogenic effects of the two compounds MDMA and MDA. However, (S)-MDA has a higher efficacy in stimulating the 5-HT_2A receptor than (R)-MDMA; thus MDA tends to cause more psychedelic-like effects, such as visual hallucinations. MDMA can also produce psychedelic-like visual effects, though these are generally less pronounced than those of MDA, or require a heavier dose to become apparent.

Pharmacokinetics

The "S" optical isomer of MDA is more potent than the "R" optical isomer as a psychostimulant, possessing greater affinity for the three monoamine transporter proteins (SERT, NET and DAT). The duration of the drug has been reported as about 6 to 8 hours.

Physical and chemical properties

Synthesis

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.

Detection in body fluids

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.

History

MDA was first synthesized by C. Mannich and W. Jacobsohn in 1910. It was first ingested in July 1930 by Gordon Alles who later licensed the drug to Smith, Kline & French. 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 & 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 with 450 mg of the drug. MDA was patented as a cough suppressant by H. D. Brown in 1958, 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.

Legal Status

Australia

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."

Research

In 2010, Matthew Baggott and colleagues studied the ability of MDA to invoke mystical experiences and alter vision in healthy volunteers.

External links

• Erowid MDA Vault
• MDA entry in PiHKAL
• MDA entry in PiHKAL • info