2,5-Dimethoxyamphetamine

2,5-Dimethoxyamphetamine
Clinical data
Other names	2,5-DMA; 2,5-Dimethoxy-α-methylphenethylamine; DMA; DMA-4; DOH; NSC-367445
Routes of; administration	Oral
Drug class	Serotonin 5-HT2A receptor agonist
Pharmacokinetic data
Duration of action	6–8 hours
Identifiers
	IUPAC name 1-(2,5-dimethoxyphenyl)propan-2-amine;
CAS Number	2801-68-5;
PubChem CID	62787;
DrugBank	DB01465;
ChemSpider	56526;
UNII	OIM1536TQQ;
KEGG	C22738;
ChEMBL	ChEMBL8642;
CompTox Dashboard (EPA)	DTXSID2091540 ;
ECHA InfoCard	100.018.673
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=C(C=CC(=C1)OC)OC)N;
	InChI InChI=1S/C11H17NO2/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3; Key:LATVFYDIBMDBSY-UHFFFAOYSA-N;

2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a drug of the phenethylamine and amphetamine families.^[1]^[2] It is one of the dimethoxyamphetamine (DMA) series of positional isomers.^[1]^[2] The drug is notable in being the parent compound of the DOx (4-substituted-2,5-dimethoxyamphetamine) series of drugs.^[1]^[2]

^ ^a ^b ^c ^d ^e Shulgin AT, Shulgin A (1991). "#54 2,5-DMA; DMA; 2,5-DIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 9780963009609. OCLC 25627628.
^ ^a ^b ^c ^d ^e Shulgin A, Manning T, Daley PF (2011). "#36. 2,5-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.

[PiHKAL-1] Shulgin AT, Shulgin A (1991). "#54 2,5-DMA; DMA; 2,5-DIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 9780963009609. OCLC 25627628.

[ShulginManningDaley2011-2] Shulgin A, Manning T, Daley PF (2011). "#36. 2,5-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.

[1]

[2]