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; Stimulant
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.^[3]^[4]^[5] It is usually taken orally.^[3]^[5]

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.^[3] It has a duration of 5 to 8 hours.^[3]^[2]

MDA has a long history of psychotherapeutic and recreational use that predates that of MDMA, dating back to at least the mid-1960s.^[3]^[6]^[4] It has been described as the first entactogen.^[2] MDA has also been described as probably the most popular analogue of MDMA.^[6] In most countries, the drug is a controlled substance and its possession and sale are illegal.

^ "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.
^ ^a ^b ^c ^d Cite error: The named reference BaggottGarrisonCoyle2019 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
^ ^a ^b Kaur H, Karabulut S, Gauld JW, Fagot SA, Holloway KN, Shaw HE, Fantegrossi WE (September 2023). "Balancing Therapeutic Efficacy and Safety of MDMA and Novel MDXX Analogues as Novel Treatments for Autism Spectrum Disorder". Psychedelic Medicine. 1 (3): 166–185. doi:10.1089/psymed.2023.0023. PMC 11661495. PMID 40046567.
^ ^a ^b Alexander T. Shulgin, Ann Shulgin (1991). "#100 MDA 3,4-METHYLENEDIOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. pp. 714–719. ISBN 978-0-9630096-0-9. OCLC 25627628.
^ ^a ^b Sáez-Briones P, Hernández A (September 2013). "MDMA (3,4-Methylenedioxymethamphetamine) Analogues as Tools to Characterize MDMA-Like Effects: An Approach to Understand Entactogen Pharmacology". Curr Neuropharmacol. 11 (5): 521–534. doi:10.2174/1570159X11311050007. PMC 3763760. PMID 24403876.

[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.

[BaggottGarrisonCoyle2019-2] Cite error: The named reference BaggottGarrisonCoyle2019 was invoked but never defined (see the help page).

[Oeri2021-3] ^ ^a ^b ^c ^d ^e ^f Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.

[HarpreetKarabulutGauld2023-4] Kaur H, Karabulut S, Gauld JW, Fagot SA, Holloway KN, Shaw HE, Fantegrossi WE (September 2023). "Balancing Therapeutic Efficacy and Safety of MDMA and Novel MDXX Analogues as Novel Treatments for Autism Spectrum Disorder". Psychedelic Medicine. 1 (3): 166–185. doi:10.1089/psymed.2023.0023. PMC 11661495. PMID 40046567.

[PiHKAL1991-5] Alexander T. Shulgin, Ann Shulgin (1991). "#100 MDA 3,4-METHYLENEDIOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. pp. 714–719. ISBN 978-0-9630096-0-9. OCLC 25627628.

[Sáez-BrionesHernández2013-6] Sáez-Briones P, Hernández A (September 2013). "MDMA (3,4-Methylenedioxymethamphetamine) Analogues as Tools to Characterize MDMA-Like Effects: An Approach to Understand Entactogen Pharmacology". Curr Neuropharmacol. 11 (5): 521–534. doi:10.2174/1570159X11311050007. PMC 3763760. PMID 24403876.

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