3,4-Methylenedioxyamphetamine

3,4-Methylenedioxyamphetamine
INN: Tenamfetamine
Clinical data
Other names	MDA; Tenamfetamine; Amphedoxamine; Sally; Sassafras; Sass-a-frass; Sass; Mellow Drug of America; Hug drug; Love; 3,4-Methylenedioxy-α-methylphenethylamine; 5-(2-Aminopropyl)-1,3-benzodioxole; EA-1298; NSC-9978; NSC-27106; SKF-5
Routes of; administration	By mouth, sublingual, insufflation, intravenous
Drug class	Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Empathogen; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Metabolism	Hepatic (CYP extensively involved)
Elimination half-life	10.9 hours
Duration of action	5–8 hours
Excretion	Renal
Identifiers
	IUPAC name 1-(2H-1,3-Benzodioxol-5-yl)propan-2-amine;
CAS Number	4764-17-4 ;
PubChem CID	1614;
DrugBank	DB01509 ;
ChemSpider	1555 ;
UNII	XJZ28FJ27W;
KEGG	D12715 ;
ChEBI	CHEBI:166520;
ChEMBL	ChEMBL6731 ;
CompTox Dashboard (EPA)	DTXSID40859958 ;
ECHA InfoCard	100.230.706
Chemical and physical data
Formula	C10H13NO2
Molar mass	179.219 g·mol−1
3D model (JSmol)	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 ; Key:NGBBVGZWCFBOGO-UHFFFAOYSA-N ;
	(verify)

3,4-Methylenedioxyamphetamine (MDA) is an entactogen, stimulant, and psychedelic drug of the amphetamine and MDxx families that is encountered mainly as a recreational drug. It is usually taken orally.

In terms of its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and a serotonin 5-HT₂ receptor agonist, including of the serotonin 5-HT_2A receptor. It has a duration of 5 to 8 hours.

MDA has a long history of psychotherapeutic and recreational use that predates that of MDMA, dating back to at least the mid-1960s. It has been described as the first entactogen. MDA has also been described as probably the most popular analogue of MDMA. In most countries, the drug is a controlled substance and its possession and sale are illegal.

Clinical data


Other names	MDA; Tenamfetamine; Amphedoxamine; Sally; Sassafras; Sass-a-frass; Sass; Mellow Drug of America; Hug drug; Love; 3,4-Methylenedioxy-α-methylphenethylamine; 5-(2-Aminopropyl)-1,3-benzodioxole; EA-1298; NSC-9978; NSC-27106; SKF-5
Routes of administration	By mouth, sublingual, insufflation, intravenous
Drug class	Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT₂ receptor agonist; Entactogen; Empathogen; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics) CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I UN: Psychotropic Schedule I
Pharmacokinetic data
Metabolism	Hepatic (CYP extensively involved)
Elimination half-life	10.9 hours
Duration of action	5–8 hours
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
KEGG	D12715^Y
ChEBI	CHEBI:166520
ChEMBL	ChEMBL6731^Y
CompTox Dashboard (EPA)	DTXSID40859958
ECHA InfoCard	100.230.706
Chemical and physical data
Formula	C₁₀H₁₃NO₂
Molar mass	179.219 g·mol⁻¹
3D model (JSmol)	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
(verify)