同: MDA

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3,4-Methylenedioxyamphetamine (MDA), also known as tenamphetamine (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, 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 then 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. One human subject^[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). Although there is some debate, the duration of the drug is sometimes believed^{[by whom?]} to be 6 to 10 hours; but most individuals 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.

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).^[4] The website erowid.org lists the fatality rate at roughly 2 in 100,000 users, assuming it has similar rates as MDMA.^[5] The median lethal dose (LD₅₀) in mice has been reported as 92 mg/kg by intraperitoneal injection.Template:Https://www.erowid.org/psychoactives/health/psychoactives ld50s.shtml

Pharmacology

MDA is a human TAAR1 agonist.^[6]

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. PMID 8246240. Retrieved 20 January 2014.
^ 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

Oral fluid and plasma 3,4-methylenedioxymethamphetamine (MDMA) and metabolite correlation after controlled oral MDMA administration.

Desrosiers NA, Barnes AJ, Hartman RL, Scheidweiler KB, Kolbrich-Spargo EA, Gorelick DA, Goodwin RS, Huestis MA.SourceChemistry and Drug Metabolism Section, Clinical Pharmacology and Therapeutic Research Branch, NIDA IRP, 251 Bayview Boulevard, Suite 200 Room 05A-721, Baltimore, MD, 21224, USA.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2013 May;405(12):4067-76. doi: 10.1007/s00216-013-6848-7. Epub 2013 Mar 8.
Oral fluid (OF) offers a noninvasive sample collection for drug testing. However, 3,4-methylenedioxymethamphetamine (MDMA, ecstasy) in OF has not been adequately characterized in comparison to plasma. We administered oral low-dose (1.0 mg/kg) and high-dose (1.6 mg/kg) MDMA to 26 participants and c
PMID 23471370

Simultaneous determination of opiates, methadone, amphetamines, cocaine, and metabolites in human placenta and umbilical cord by LC-MS/MS.

de Castro A, Díaz A, Piñeiro B, Lendoiro E, Cruz A, López-Rivadulla M, Concheiro M.SourceToxicology Service, Institute of Forensic Sciences, University of Santiago de Compostela, San Francisco s/n, 15782, Santiago de Compostela, Spain, ana.decastro@usc.es.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2013 May;405(12):4295-305. doi: 10.1007/s00216-013-6784-6. Epub 2013 Feb 10.
LC-MS/MS methods for the quantification of morphine, morphine-3-glucuronide, morphine-6-glucuronide, codeine, 6-acetylmorphine, cocaine, benzoylecgonine, ecgonine methyl ester, hydroxybenzoylecgonine, cocaethylene, amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymetham
PMID 23397092

5-Iodo-2-aminoindan (5-IAI): chemistry, pharmacology, and toxicology of a research chemical producing MDMA-like effects.

Coppola M, Mondola R.SourceDepartment of Addiction, ASL CN2, Viale Coppino 46, 12051 Alba (CN), Italy. coppolamail@alice.it
Toxicology letters.Toxicol Lett.2013 Mar 27;218(1):24-9. doi: 10.1016/j.toxlet.2013.01.008. Epub 2013 Jan 21.
In 2010, an internet snapshot of EMCDDA anticipated the presence of 5-iodo-2-aminoindan (5-IAI) within the recreational drug market. In 2011, this compound, a psychoactive derivative of 2-aminoindane, was identified in recreational products sold in the United Kingdom. 5-IAI is a rigid analogue of p-
PMID 23347877

Japanese Journal

Direct Analysis in Real Time (DART)-TOFMSを用いた尿中覚せい剤及び 3,4-methylenedioxymethamphetamine (MDMA) 迅速スクリーニング法の検討

河村麻衣子,花尻(木倉) 瑠理,合田幸広
YAKUGAKU ZASSHI 131(5), 827-833, 2011
… In this study, we investigated rapid screening methods of illicit drugs and their metabolites, such as methamphetamine (MA), 3,4-methylenedioxymethamphetamine (MDMA), amphetamine (AP) and 3,4-methylenedioxyamphetamine (MDA) in human urine using DART-TOFMS. …
NAID 130000678865

Recreational drugs, 3,4-Methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and diphenylprolinol, inhibit neurite outgrowth in PC12 cells

KAIZAKI Asuka,TANAKA Sachiko,TSUJIKAWA Kenji,NUMAZAWA Satoshi,YOSHIDA Takemi
Journal of toxicological sciences 35(3), 375-381, 2010-06-01
… Thus, the present study examined the effect of recreational drugs, such as MDMA, 3,4-methylenedioxyamphetamine (MDA) and diphenylprolinol, a novel recreational drug with a similar chemical structure as that of psychoactive agent pipradrol, on nerve growth factor (NGF)-induced neurite outgrowth. …
NAID 10026469818

Related Pictures

★リンクテーブル★

リンク元	「MDA」「メチレンジオキシアンフェタミン」
拡張検索	「N-methyl-3,4-methylenedioxyamphetamine」「3,4-methylenedioxyamphetamine」

「MDA」

3,4-Methylenedioxyamphetamine
Systematic (IUPAC) name
	(R) 1-(benzo[1,3]dioxol-5-yl)propan-2-amine
Clinical data
Legal status	Prohibited (S9) (AU) Schedule III (CA) Class A (UK) Schedule I (US)
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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