2-Hydroxy-4,5-methylenedioxymethamphetamine

vanc 6 6-Hydroxy-MDMA 6-[2-(Methylamino)propyl]-2H-1,3-benzodioxol-5-ol 2-Hydroxy-MDMA.svg 6-Hydroxy-MDMA.png 175px 138808-79-4 none 6-MDMOH; 6-OH MDMA; 6-Hydroxy-MDMA; 6-Hydroxy-3,4-methylendioxymethamphetamine 11 15 1 3 CC(CC1=CC2=C(C=C1O)OCO2)NC 1S/C11H15NO3/c1-7(12-2)3-8-4-10-11(5-9(8)13)15-6-14-10/h4-5,7,12-13H,3,6H2,1-2H3 RQQIIXFYTHWFKW-UHFFFAOYSA-N 2-Hydroxy-4,5-methylenedioxymethamphetamine (6-hydroxy-3,4-methylendioxymethamphetamine) It is a non-neurotoxic metabolite of the drug 3,4-methylenedioxymethamphetamine, structurally related to 2-hydroxy-4,5-methylenedioxyamphetamine; it is detected in the brains and plasma of rats but not in their urine. It did not alter the levels of norepinephrine, glutathione, glial fibrillary acidic protein, or serotonin. Walker TM, Davenport-Jones JE, Fox RM, Atterwill CK The neurotoxic effects of methylenedioxymethamphetamine (MDMA) and its metabolites on rat brain spheroids in culture Cell Biology and Toxicology 15 3 137–142 June 1999 10580546 10.1023/a:1007658501306 Lim HK, Foltz RL In vivo formation of aromatic hydroxylated metabolites of 3,4-(methylenedioxy)methamphetamine in the rat: identification by ion trap tandem mass spectrometric (MS/MS and MS/MS/MS) techniques Biological Mass Spectrometry 20 11 677–686 November 1991 1686830 10.1002/bms.1200201105 Chu T, Kumagai Y, DiStefano EW, Cho AK Disposition of methylenedioxymethamphetamine and three metabolites in the brains of different rat strains and their possible roles in acute serotonin depletion Biochemical Pharmacology 51 6 789–796 March 1996 8602874 10.1016/0006-2952(95)02397-6 Elayan I, Gibb JW, Hanson GR, Foltz RL, Lim HK, Johnson M Long-term alteration in the central monoaminergic systems of the rat by 2,4,5-trihydroxyamphetamine but not by 2-hydroxy-4,5-methylenedioxymethamphetamine or 2-hydroxy-4,5-methylenedioxyamphetamine European Journal of Pharmacology 221 2–3 281–288 October 1992 1358654 10.1016/0014-2999(92)90714-f References Category:Methylenedioxyamphetamines Category:Recreational drug metabolites