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N-Hydroxy-AMT

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N-Hydroxy-AMT
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
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] It is not a controlled substance in Canada as of 2025.[7]

See also

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References

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  1. ^ a b c d e f Benington F, Morin RD, Clark LC (January 1965). "Behavioral and Neuropharmacological Actions of N-Aralkylhydroxylamines and Their O-Methyl Ethers". Journal of Medicinal Chemistry. 8: 100–104. doi:10.1021/jm00325a020. PMID 14287236.
  2. ^ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  3. ^ Cassels BK, Sáez-Briones P (October 2018). "Dark Classics in Chemical Neuroscience: Mescaline". ACS Chemical Neuroscience. 9 (10): 2448–2458. doi:10.1021/acschemneuro.8b00215. PMID 29847089. These examples illustrate the difficulties that defining psychotomimetic or hallucinogenic entails and support the preference of the term psychedelic.126,127 All these words imply human subjective experiences, hard to reconcile with a "rage reaction" or spontaneous brain electrical activity in cats, disruption of rope climbing by rats, or other animal models. In later years, stimulus generalization by rats trained to respond to known drugs, head shakes or twitches in rats or mice, or a panel of several different behavioral responses have been used to identify psychedelic compounds, but none of these approaches is entirely satisfactory. Therefore, what we know about the structure−activity relationships of these compounds in such models may not faithfully reflect human drug experiences.
  4. ^ Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". In Jacobs BL (ed.). Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237. Examples of common animal models that have been used over the last decade include the following: (a) disruption of the conditioned avoidance response in rats (27), (b) mouse head twitch (43), (c) rabbit hyperthermia (I), (d) cat rage response (244) and cat limb flick (121), (e) mouse ear scratch (135,251), (f) flexor and stepping reflex in chronic spinal dog (140, 143), (g) serotonin syndrome in rats (118), (h) tactile startle response in rats (68), and (i) two-lever drug discrimination in rats (84).
  5. ^ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  6. ^ a b Taschwer M, Ebner E, Schmid M (2016). "Test purchase of new synthetic tryptamines via the Internet: Identity check by GC-MS and separation by HPLC" (PDF). Journal of Applied Pharmaceutical Science: 028–034. doi:10.7324/JAPS.2016.600105. ISSN 2231-3354. Retrieved 17 November 2025.
  7. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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