5-MeO-AMT

5-MeO-AMT
Clinical data
Other names	5-MeO-AMT; 5-Methoxy-α-methyltryptamine; α,O-Dimethylserotonin; α,O-DMS; Alpha-O
Routes of; administration	Oral
Drug class	Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Unscheduled; DE: NpSG (Industrial and scientific use only); UK: Class A; US: The DEA considers 5-MeO-AMT a controlled substance analogue.; Illegal in Sweden and Florida;
Pharmacokinetic data
Duration of action	12–18 hours
Identifiers
	IUPAC name 1-(5-methoxy-1H-indol-3-yl)propan-2-amine;
CAS Number	1137-04-8 ;
PubChem CID	36906;
ChemSpider	33864 ;
UNII	U5XOB9AQ15;
ChEBI	CHEBI:125422;
ChEMBL	ChEMBL31115 ;
CompTox Dashboard (EPA)	DTXSID60893758 ;
Chemical and physical data
Formula	C12H16N2O
Molar mass	204.273 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	216 to 218 °C (421 to 424 °F)
	SMILES N[C@@H](C)CC1=CNC(C=C2)=C1C=C2OC;
	InChI InChI=1S/C12H16N2O/c1-8(13)5-9-7-14-12-4-3-10(15-2)6-11(9)12/h3-4,6-8,14H,5,13H2,1-2H3 ; Key:OGNJZVNNKBZFRM-UHFFFAOYSA-N ;
	(verify)

5-MeO-αMT, also known as 5-methoxy-α-methyltryptamine or as α,O-dimethylserotonin (α,O-DMS or Alpha-O), is a serotonergic psychedelic of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families.^[1] It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.^[1] The drug is said to be the most potent psychedelic of the simple indolealkylamines (i.e., tryptamines).^[4] It is active at oral doses of 2 to 4 mg.^[4]^[1]

^ ^a ^b ^c ^d ^e Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
^ "5-MeO-AMT; Fast Facts". National Drug Intelligence Center. January 1, 2006. Archived from the original on June 3, 2023. Retrieved July 5, 2023.
^ Anvisa (2023-07-24). "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] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ ^a ^b Vangveravong S (1994). "Synthesis of trans-2-(indol-3-yl)cyclopropylamines: Rigid tryptamine analogues". ProQuest. ProQuest 304131663. Retrieved 22 March 2025. Figure 5. Rigid Serotonin Receptor Ligands [...]