2,5-Dimethoxy-4-amylamphetamine

DOAM
Clinical data
Other names	DOAM; 2,5-Dimethoxy-4-amylamphetamine; 4-Amyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-pentylamphetamine; 4-Pentyl-2,5-dimethoxyamphetamine
Routes of; administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name 1-(2,5-dimethoxy-4-pentylphenyl)propan-2-amine;
CAS Number	63779-90-8 ;
PubChem CID	12262512;
ChemSpider	10440619 ;
UNII	N80EWL36CB;
ChEMBL	ChEMBL161416 ;
CompTox Dashboard (EPA)	DTXSID50482958 ;
Chemical and physical data
Formula	C16H27NO2
Molar mass	265.397 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=CC(OC)=C(CC(C)N)C=C1OC;
	InChI InChI=1S/C16H27NO2/c1-5-6-7-8-13-10-16(19-4)14(9-12(2)17)11-15(13)18-3/h10-12H,5-9,17H2,1-4H3 ; Key:VLJORLCVOAUUKM-UHFFFAOYSA-N ;
	(verify)

2,5-Dimethoxy-4-amylamphetamine (DOAM), also known as 2,5-dimethoxy-4-pentylamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. It is the derivative of DOM in which the methyl group at the 4 position has been replaced with an amyl (pentyl) group. The drug is taken orally.

It is a serotonin receptor agonist, including of the serotonin 5-HT_2A receptor. The drug produces weak and mixed psychedelic-like effects in animals.

DOAM was first described in the scientific literature by Alexander Shulgin and colleagues in 1975. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).