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3,4-Methylenedioxyamphetamine (MDA), also known as tenamfetamine (INN), or with the street name "Sally" or "Sass" or "Sass-a-frass", is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes. 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^{[citation needed]}, psychonautics, and as an agent in psychedelic psychotherapy. 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.

Medical use

There are no currently accepted medical uses for MDA. However, researchers have investigated many possible uses in the past. It was first ingested in July 1930 by Gordon Alles who later licensed the drug to Smith Kline and French.^[1] 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^[2] 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. Several researchers, including Claudio Naranjo and Richard Yensen, have explored MDA in the field of psychotherapy.

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 as a recreational 'love drug', due to its enhancement of empathy.^[3]

Effects

The MDA molecule

A recreational dose of MDA is commonly between 100 and 160 mg. 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;^[4] but some individuals^{[citation needed]} report the duration of the drug's effects to be around 5–6 hours, slightly longer than that of MDMA. (In the late 1990s, Alexander Shulgin changed his opinion of the duration to 3–6 hours).

MDA is thought to be similar in pharmacological mechanism of action and phenomenological effects to its more widely used N-methyl analog, MDMA. MDA causes serotonin and dopamine release by acting as a substrate at the SERT and DAT, respectively. 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.

MDA is said to share the entactogenic effects of MDMA. While it is generally similar to MDMA, users report that MDA has more stimulant and psychedelic qualities and slightly less intense entactogenic effects than MDMA. MDA is also considered less predictable than MDMA, with effects varying greatly from person to person. However, no properly controlled experiments have compared these drugs in humans. MDA was best known for its enhancement of the experiences of dancing and sex.^{[citation needed]}

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).^[5] The website erowid.org lists the fatality rate at roughly 2 in 100,000 users, assuming it has similar rates as MDMA.^[6] The median lethal dose (LD₅₀) in mice has been reported as 92 mg/kg by intraperitoneal injection.

Pharmacology

MDA is a human TAAR1 agonist.^[7]

References

^ The First MDA trip and the measurement of ‘mystical experience’ after MDA, LSD, and Psilocybin http://psychedelicresearch.org/?p=45
^ The History Channel documented details of his death here http://www.youtube.com/watch?v=ySw-0uY4CUA See minute 2:38 onward.
^ Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE. (1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry 36 (23): 3700–3706. doi:10.1021/jm00075a027. PMID 8246240. Retrieved 20 January 2014.
^ Baggott MJ, Siegrist JD, Galloway GP, Robertson LC, Coyle JR, Mendelson, JE. Investigating the Mechanisms of Hallucinogen-Induced Visions Using 3,4-Methylenedioxyamphetamine (MDA): A Randomized Controlled Trial in Humans. DOI: 10.1371/journal.pone.0014074
^ Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.
^ Erowid.org
^ Lewin AH, Miller GM, Gilmour B (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorg. Med. Chem. 19 (23): 7044–8. doi:10.1016/j.bmc.2011.10.007. PMC 3236098. PMID 22037049.

Lee, M.A. and Shlain, B., Acid Dreams: The CIA, LSD, and the Sixties Rebellion. Grove, 1985.
Stafford, P. Psychedelics Encyclopedia. Ronin, 1992.
Pihkal: A Chemical Love Story, Transform Press, Alexander Shulgin, Ann Shulgin.

External links

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

UpToDate Contents

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English Journal

Evaluation of drug incorporation into hair segments and nails by enantiomeric analysis following controlled single MDMA intakes.

Madry MM1, Steuer AE2, Hysek CM3, Liechti ME3, Baumgartner MR1, Kraemer T4.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2016 Jan;408(2):545-56. doi: 10.1007/s00216-015-9130-3. Epub 2015 Oct 31.
Incorporation rates of the enantiomers of 3,4-methylenedioxymethamphetamine (MDMA) and its metabolite 3,4-methylenedioxyamphetamine (MDA) into hair and nails were investigated after controlled administration. Fifteen subjects without MDMA use received two doses of 125 mg of MDMA. Hair, nail scrapin
PMID 26521178

Binding Mode Selection Determines the Action of Ecstasy Homologs at Monoamine Transporters.

Sandtner W1, Stockner T1, Hasenhuetl PS1, Partilla JS1, Seddik A1, Zhang YW1, Cao J1, Holy M1, Steinkellner T1, Rudnick G1, Baumann MH1, Ecker GF1, Newman AH1, Sitte HH2.
Molecular pharmacology.Mol Pharmacol.2016 Jan;89(1):165-75. doi: 10.1124/mol.115.101394. Epub 2015 Oct 30.
Determining the structural elements that define substrates and inhibitors at the monoamine transporters is critical to elucidating the mechanisms underlying these disparate functions. In this study, we addressed this question directly by generating a series of N-substituted 3,4-methylenedioxyampheta
PMID 26519222

Chiral Plasma Pharmacokinetics of 3,4-Methylenedioxymethamphetamine and its Phase I and II Metabolites following Controlled Administration to Humans.

Steuer AE1, Schmidhauser C2, Schmid Y2, Rickli A2, Liechti ME2, Kraemer T2.
Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2015 Dec;43(12):1864-71. doi: 10.1124/dmd.115.066340. Epub 2015 Sep 22.
Generally, pharmacokinetic studies on 3,4-methylenedioxymethamphetamine (MDMA) in blood have been performed after conjugate cleavage, without taking into account that phase II metabolites represent distinct chemical entities with their own effects and stereoselective pharmacokinetics. The aim of the
PMID 26395866

Japanese Journal

Probe Heating Method for the Analysis of Solid Samples Using a Portable Mass Spectrometer

Mass Spectrometry 4(1), A0038-A0038, 2015
NAID 130005066557

Crystal Structure of a Fluoro Analogue of 3,4-(Methylenedioxy)amphetamine

X-ray Structure Analysis Online 31(0), 23-24, 2015
NAID 130005065554

毛髪中覚せい剤類分析の自動化と高感度化を目指したガスクロマトグラフィー／質量分析システムの開発

日本法科学技術学会誌 17(1), 27-34, 2012
NAID 130004942639

「3,4-メチレンジオキシアンフェタミン」

3,4-Methylenedioxyamphetamine
Systematic (IUPAC) name
	(R) 1-(benzo[1,3]dioxol-5-yl)propan-2-amine
Clinical data
Legal status	AU: Prohibited (S9); CA: Schedule III; UK: Class A; US: Schedule I;
Routes	Oral, Sublingual, Intranasal
Pharmacokinetic data
Metabolism	Hepatic, CYP extensively involved
Half-life	unknown
Excretion	Renal
Identifiers
CAS number	4764-17-4
ATC code	?
PubChem	CID 1614
DrugBank	DB01509
ChemSpider	1555
ChEMBL	CHEMBL6731
Chemical data
Formula	C10H13NO2
Mol. 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 ; Key:NGBBVGZWCFBOGO-UHFFFAOYSA-N ;
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　　[★]

英: 3,4-methylenedioxyamphetamine
関: 合成麻薬

「N-methyl-3,4-methylenedioxyamphetamine」

　　[★] N-メチル-3,4-メチレンジオキシアンフェタミン

「methylenedioxyamphetamine」

　　[★]

メチレンジオキシアンフェタミン

同: MDA

[1] The First MDA trip and the measurement of ‘mystical experience’ after MDA, LSD, and Psilocybin http://psychedelicresearch.org/?p=45

[2] The History Channel documented details of his death here http://www.youtube.com/watch?v=ySw-0uY4CUA See minute 2:38 onward.

[3] Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE. (1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry 36 (23): 3700–3706. doi:10.1021/jm00075a027. PMID 8246240. Retrieved 20 January 2014.

[Baggott-4] Baggott MJ, Siegrist JD, Galloway GP, Robertson LC, Coyle JR, Mendelson, JE. Investigating the Mechanisms of Hallucinogen-Induced Visions Using 3,4-Methylenedioxyamphetamine (MDA): A Randomized Controlled Trial in Humans. DOI: 10.1371/journal.pone.0014074

[Diaz-5] Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.

[6] Erowid.org

[pmid22037049-7] Lewin AH, Miller GM, Gilmour B (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorg. Med. Chem. 19 (23): 7044–8. doi:10.1016/j.bmc.2011.10.007. PMC 3236098. PMID 22037049.

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3,4-methylenedioxyamphetamine