N-Hydroxy-DOM

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N-Hydroxy-DOM
File:N-Hydroxy-DOM.svg
Clinical data
Other namesN-HO-DOM; 4-Methyl-2,5-dimethoxy-N-hydroxyamphetamine; 2,5-Dimethoxy-4-methyl-N-hydroxyamphetamine; DOM-OH
Drug classPossible serotonergic psychedelic or hallucinogen
ATC code
  • None
Identifiers
  • N-[1-(2,5-dimethoxy-4-methylphenyl)propan-2-yl]hydroxylamine
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
  • CC1=CC(=C(C=C1OC)CC(C)NO)OC
  • InChI=1S/C12H19NO3/c1-8-5-12(16-4)10(6-9(2)13-14)7-11(8)15-3/h5,7,9,13-14H,6H2,1-4H3
  • Key:JAIPYOTXVGSAEO-UHFFFAOYSA-N

N-Hydroxy-DOM, also known as 4-methyl-2,5-dimethoxy-N-hydroxyamphetamine or as DOM-OH, is a possible psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM.[1][2][3] It is the N-hydroxy derivative of DOM.[1][2][3] The drug was not included nor mentioned by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) and its properties and effects in humans are unknown.[4][3] N-Hydroxy-DOM was reported to produce DOM-like behavioral and physiological effects in rats, including pupil dilation and hypolocomotion among others, but was 6-fold less potent than DOM in this species.[1][5] It also appears to be a metabolite of DOM formed by the liver in rabbits.[2] Other N-hydroxy derivatives of phenethylamines such as the HOT-x series like HOT-2 (N-hydroxyl-2C-T-2) as well as MDOH (N-hydroxy-MDA) may act as prodrugs of their N-unsubstituted analogues.[4] The chemical synthesis of N-hydroxy-DOM has been described.[5] N-Hydroxy-DOM was first described in the scientific literature by Ronald Coutts and Jerry Malicky by 1973.[5][6]

See also

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References

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