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]