N-Hydroxy-AMT

N-Hydroxy-AMT, or N-HO-AMT, also known as N-hydroxy-α-methyltryptamine, is a possible psychedelic drug of the tryptamine and α-alkyltryptamine families related to α-methyltryptamine (AMT).^[1] It is the N-hydroxy derivative of AMT.^[1] The drug was not mentioned in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved) and its properties and effects in humans are unknown.^[2] In preclinical research, N-hydroxy-AMT produces stimulant-like effects in mice such as hyperlocomotion and antagonism of hexobarbital-induced sleeping time, pressor effects in cats, and a psychedelic-like rage reaction in cats.^[1][3][4] Unlike AMT, it is not a monoamine oxidase inhibitor (MAOI) in vitro.^[1] N-Hydroxy derivatives of phenethylamines such as the HOT-x series like HOT-2 as well as MDOH may act as prodrugs of their N-unsubstituted forms.^[5] The chemical synthesis^[1] and analytical detection of N-hydroxy-AMT have been described.^[6] N-Hydroxy-AMT was first described in the scientific literature by F. Benington and colleagues in 1965.^[1][6]

N-Hydroxy-AMT

Clinical data
Other names	N-HO-AMT; N-Hydroxy-α-methyltryptamine
Drug class	Possible psychedelic drug or hallucinogen; Stimulant
ATC code	None
Identifiers
IUPAC name N-[1-(1H-indol-3-yl)propan-2-yl]hydroxylamine
CAS Number	63-33-2
PubChem CID	56728
ChemSpider	51154
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CNC2=CC=CC=C21)NO
InChI InChI=1S/C11H14N2O/c1-8(13-14)6-9-7-12-11-5-3-2-4-10(9)11/h2-5,7-8,12-14H,6H2,1H3 Key:QDEFFOYILHFBSE-UHFFFAOYSA-N

See also

• Substituted α-alkyltryptamine