2,5-Dimethoxy-4-amylamphetamine

2,5-Dimethoxy-4-amylamphetamine (DOAM), also known as 2,5-dimethoxy-4-pentylamphetamine, is a lesser-known serotonin receptor agonist and serotonergic psychedelic of the amphetamine and DOx families.^[1]

2,5-Dimethoxy-4-amylamphetamine

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[1]
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name 1-(2,5-dimethoxy-4-pentylphenyl)propan-2-amine
CAS Number	63779-90-8 Y
PubChem CID	12262512
ChemSpider	10440619 Y
UNII	N80EWL36CB
ChEMBL	ChEMBL161416 Y
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 Y Key:VLJORLCVOAUUKM-UHFFFAOYSA-N Y
(verify)

Effects

DOAM was first synthesized by Alexander Shulgin.^[1] In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 10 mg orally and the duration is unknown.^[1] DOAM was reported to produce a bare threshold and tenseness.^[1] In other publications however, DOAM has been said to produce threshold effects at 5 to 10 mg orally and to be hallucinogenic at a dose of 40 mg, with about 10-fold higher potency than mescaline.^[2][3][4] In any case, it shows far lower psychedelic potency than other DOx drugs such as DOM.^[2][3] No qualitative description of its effects at hallucinogenic doses is available.^[3][1]

Pharmacology

DOAM has been found to be a moderate-efficacy partial agonist of the serotonin 5-HT_2A receptor.^[5] It also shows lower affinity for the serotonin 5-HT_2C receptor, whereas it has very low affinity for the serotonin 5-HT_1A receptor.^[5] The drug is inactive as an agonist of the serotonin 5-HT_2B receptor.^[5] DOAM shows very low potency as a human trace amine-associated receptor 1 (TAAR1) agonist.^[5] It does not bind to the monoamine transporters.^[5]

DOAM fails to substitute for DOM in rodent drug discrimination tests, producing up to 35% responding followed up behavioral disruption at higher doses.^[6][7][8] It was also unable to antagonize the DOM stimulus at the assessed doses, and behavioral disruption at higher doses prevented further assessment.^[9]

As the 4-alkyl chain length in DOx is increased from shorter homologues such as DOM, DOET and DOPR which are all potent hallucinogens, the serotonin 5-HT₂ receptor binding affinity increases, rising to a maximum with DOHx before falling again with even longer chains. Compounds with sufficiently long chains, such as DOAM, or with bulky groups such as DOTB, fail to produce full psychedelic-like effects in animals and/or humans. These findings suggest that such compounds may act as low-efficacy partial agonists or antagonists of the serotonin 5-HT_2A receptor.^{[10][7][11][12]}

See also

• 2,5-Dimethoxy-4-butylamphetamine (DOBU)
• 2,5-Dimethoxy-4-hexylamphetamine (DOHx)