N-Hydroxy-AMT

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N-Hydroxy-AMT
File:N-Hydroxy-AMT.svg
File:N-Hydroxy-AMT 3D.png
Clinical data
Other namesN-HO-AMT; N-Hydroxy-α-methyltryptamine
Drug classPossible psychedelic drug or hallucinogen; Stimulant
ATC code
  • None
Identifiers
  • N-[1-(1H-indol-3-yl)propan-2-yl]hydroxylamine
CAS Number
PubChem CID
ChemSpider
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
  • CC(CC1=CNC2=CC=CC=C21)NO
  • 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

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]

See also

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References

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