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| Other names | N-HO-DOM; 4-Methyl-2,5-dimethoxy-N-hydroxyamphetamine; 2,5-Dimethoxy-4-methyl-N-hydroxyamphetamine; DOM-OH |
| Drug class | Possibleserotonergic psychedelic orhallucinogen |
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| Formula | C12H19NO3 |
| Molar mass | 225.288 g·mol−1 |
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N-Hydroxy-DOM, also known as4-methyl-2,5-dimethoxy-N-hydroxyamphetamine or asDOM-OH, is a possiblepsychedelic drug of thephenethylamine,amphetamine, andDOx families related toDOM.[1][2][3] It is theN-hydroxyderivative of DOM.[1][2][3] The drug was not included or mentioned byAlexander Shulgin in his 1991 bookPiHKAL (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, includingpupil dilation andhypolocomotion among others, but was 6-fold lesspotent than DOM in this species.[1][5] It also appears to be ametabolite of DOM formed by theliver in rabbits.[2] OtherN-hydroxy derivatives of phenethylamines such as theHOT-x series likeHOT-2 (N-hydroxyl-2C-T-2) as well asMDOH (N-hydroxy-MDA) may act asprodrugs of theirN-unsubstitutedanalogues.[4] Thechemical synthesis ofN-hydroxy-DOM has been described.[5]N-Hydroxy-DOM was first described in thescientific literature by Ronald Coutts and Jerry Malicky by 1973.[5][6]
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.
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