N-Hydroxy-DOM

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. It is the N-hydroxy derivative of DOM. The drug was not included nor mentioned by Alexander Shulgin in his 1991 book PiHKAL and its properties and effects in humans are unknown. 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. It also appears to be a metabolite of DOM formed by the liver in rabbits. Other N-hydroxy derivatives of phenethylamines such as the HOT-x series like HOT-2 as well as MDOH may act as prodrugs of their N-unsubstituted analogues. The chemical synthesis of N-hydroxy-DOM has been described. N-Hydroxy-DOM was first described in the scientific literature by Ronald Coutts and Jerry Malicky by 1973. It is a controlled substance in Canada under phenethylamine blanket-ban language.