3,4-Methylenedioxyamphetamine

3,4-Methylenedioxyamphetamine
INN: Tenamfetamine
Clinical data
Routes of; administration	Oral, sublingual, insufflation, intravenous
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)
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 ;
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 ;
	(what is this?) (verify)

3,4-Methylenedioxyamphetamine (also known as MDA and sass) is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

MDA is rarely sought as a recreational drug compared to other amphetamines; however, it remains widely used due to it being a primary metabolite,^[2] the product of hepatic N-dealkylation,^[3] of MDMA (ecstasy). It is also a common adulterant of illicitly produced MDMA.^[4]^[5]

^ "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control]. Brazilian Health Regulatory Agency (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). 24 July 2023. Archived from the original on 27 August 2023. Retrieved 27 August 2023.
^ Crean RD, Davis SA, Von Huben SN, Lay CC, Katner SN, Taffe MA (October 2006). "Effects of (+/-)3,4-methylenedioxymethamphetamine, (+/-)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques". Neuroscience. 142 (2): 515–525. doi:10.1016/j.neuroscience.2006.06.033. PMC 1853374. PMID 16876329.
^ de la Torre R, Farré M, Roset PN, Pizarro N, Abanades S, Segura M, et al. (April 2004). "Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition". Therapeutic Drug Monitoring. 26 (2): 137–144. doi:10.1097/00007691-200404000-00009. PMID 15228154.
^ "EcstasyData.org: Test Result Statistics: Substances by Year". EcstasyData.org. Retrieved 27 June 2017.
^ "Trans European Drug Information". idpc.net. Archived from the original on 4 November 2021. Retrieved 27 June 2017.

[1] "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control]. Brazilian Health Regulatory Agency (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). 24 July 2023. Archived from the original on 27 August 2023. Retrieved 27 August 2023.

[2] Crean RD, Davis SA, Von Huben SN, Lay CC, Katner SN, Taffe MA (October 2006). "Effects of (+/-)3,4-methylenedioxymethamphetamine, (+/-)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques". Neuroscience. 142 (2): 515–525. doi:10.1016/j.neuroscience.2006.06.033. PMC 1853374. PMID 16876329.

[:0-3] Torre R, Farré M, Roset PN, Pizarro N, Abanades S, Segura M, et al. (April 2004). "Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition". Therapeutic Drug Monitoring. 26 (2): 137–144. doi:10.1097/00007691-200404000-00009. PMID 15228154.

[4] "EcstasyData.org: Test Result Statistics: Substances by Year". EcstasyData.org. Retrieved 27 June 2017.

[5] "Trans European Drug Information". idpc.net. Archived from the original on 4 November 2021. Retrieved 27 June 2017.

[1]

[2]

[3]

[4]

[5]

Clinical data


Routes of administration	Oral, sublingual, insufflation, intravenous
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)^[1] 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)
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
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
^NY (what is this?) (verify)