Chemistry:N-Hydroxy-DOM

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N-Hydroxy-DOM
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
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)

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] It is a controlled substance in Canada under phenethylamine blanket-ban language.[7]

See also

  • DOx (psychedelics)
  • HOT-x (psychedelics)
  • 2C-B-OH (N-hydroxy-2C-B)
  • N-Hydroxyamphetamine

References

  1. ↑ 1.0 1.1 1.2 "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences 70 (8): 839–849. August 1981. doi:10.1002/jps.2600700802. PMID 7031221. Bibcode: 1981JPhmS..70..839N. "One other active substitution on nitrogen is the N-hydroxy group. N-Hydroxylation of III gives a compound possessing clinical activity (66). Coutts and Malicky (72) evaluated several congeners of II. One, the N-hydroxy derivative (XXI), elicited behavioral effects in rats but at about six times the dosage required for II.". 
  2. ↑ 2.0 2.1 2.2 "Drug Metabolism: Review of Principles and the Fate of One-Ring Psychotomimetics". Stimulants. Boston, MA: Springer US. 1978. pp. 335–387. doi:10.1007/978-1-4757-0510-2_7. ISBN 978-1-4757-0512-6. http://link.springer.com/10.1007/978-1-4757-0510-2_7. Retrieved 17 November 2025. 
  3. ↑ 3.0 3.1 3.2 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. 
  4. ↑ 4.0 4.1 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. 
  5. ↑ 5.0 5.1 5.2 "The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)". Canadian Journal of Chemistry 51 (9): 1402–1409. 1 May 1973. doi:10.1139/v73-210. ISSN 0008-4042. 
  6. ↑ "The Synthesis of Four Possible in vitro Metabolites of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)". Canadian Journal of Chemistry 52 (3): 395–399. 1 February 1974. doi:10.1139/v74-063. ISSN 0008-4042. https://cdnsciencepub.com/doi/10.1139/v74-063. Retrieved 17 November 2025. 
  7. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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