3,4-methylenedioxyamphetamine

3,4‐Methylenedioxeamphetamine
INN: Tenamfetamine
Clinical data


Routes of administration	Oral, Sublingual, Insufflation, Intravenous
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Schedule I UN: Psychotropic Schedule I
Pharmacokinetic data
Metabolism	Hepatic, extensively involved
Excretion	Renal
Identifiers
IUPAC name 1-(2H-1,3-Benzodioxol-5-yl)propan-2-amine
CAS Number	4764-17-4^Y
PubChem (CID)	1614
DrugBank	DB01509^Y
ChemSpider	1555^Y
UNII	XJZ28FJ27W^N
ChEMBL	CHEMBL6731^Y
ECHA InfoCard	100.230.706
Chemical and physical data
Formula	C₁₀H₁₃NO₂
Molar mass	179.22 g/mol
3D model (Jmol)	Interactive image
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
^NY (what is this?)

3,4-Methylenedioxyamphetamine (MDA), also known as tenamfetamine (INN), 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 in few countries. The recreational use of MDA predates its more widely used analog MDMA (ecstasy).

MDA currently has no accepted medical use.

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.

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).

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.

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