N-Hydroxy-DOM

N-Hydroxy-DOM
Clinical data
Other names	N-HO-DOM; 4-Methyl-2,5-dimethoxy-N-hydroxyamphetamine; 2,5-Dimethoxy-4-methyl-N-hydroxyamphetamine; DOM-OH
Drug class	Possible serotonergic psychedelic or hallucinogen
ATC code	None;
Identifiers
	IUPAC name N-[1-(2,5-dimethoxy-4-methylphenyl)propan-2-yl]hydroxylamine;
CAS Number	43022-01-1;
PubChem CID	597107;
ChemSpider	519067;
UNII	05R77CAF0B;
CompTox Dashboard (EPA)	DTXSID80962859 ;
Chemical and physical data
Formula	C12H19NO3
Molar mass	225.288 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=C(C=C1OC)CC(C)NO)OC;
	InChI 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] It is a controlled substance in Canada under phenethylamine blanket-ban language.^[7]

References

1 2 3 Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences. 70 (8): 839–849. Bibcode:1981JPhmS..70..839N. doi:10.1002/jps.2600700802. PMID 7031221. 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.
1 2 3 Castagnoli N (1978). "Drug Metabolism: Review of Principles and the Fate of One-Ring Psychotomimetics". In Iversen, LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 335–387. doi:10.1007/978-1-4757-0510-2_7. ISBN 978-1-4757-0512-6. Retrieved 17 November 2025.
1 2 3 Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
1 2 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
1 2 3 Coutts RT, Malicky JL (1 May 1973). "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. doi:10.1139/v73-210. ISSN 0008-4042.
↑ Coutts RT, Malicky JL (1 February 1974). "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. doi:10.1139/v74-063. ISSN 0008-4042. Retrieved 17 November 2025.
↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

External links

N-HO-DOM - Isomer Design

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[Nichols_1981-1] 1 2 3 Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences. 70 (8): 839–849. Bibcode:1981JPhmS..70..839N. doi:10.1002/jps.2600700802. PMID 7031221. 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.

[Castagnoli_1978-2] 1 2 3 Castagnoli N (1978). "Drug Metabolism: Review of Principles and the Fate of One-Ring Psychotomimetics". In Iversen, LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 335–387. doi:10.1007/978-1-4757-0510-2_7. ISBN 978-1-4757-0512-6. Retrieved 17 November 2025.

[Shulgin_2011-3] 1 2 3 Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.

[PiHKAL-4] 1 2 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

[Coutts_1973-5] 1 2 3 Coutts RT, Malicky JL (1 May 1973). "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. doi:10.1139/v73-210. ISSN 0008-4042.

[Coutts_1974-6] Coutts RT, Malicky JL (1 February 1974). "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. doi:10.1139/v74-063. ISSN 0008-4042. Retrieved 17 November 2025.

[CDSA-7] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

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N-Hydroxy-DOM

See also

References

External links