2,4,5-Trihydroxymethamphetamine

2,4,5-trihydroxymethamphetamine.svg skin-invert-image 200px 5-[2-(Methylamino)propyl]benzene-1,2,4-triol THMA; THM 136706-32-6 correct FDA K5ZT2JD76S 131985 19983112 CNC(C)CC1=C(O)C=C(O)C(O)=C1 1S/C10H15NO3/c1-6(11-2)3-7-4-9(13)10(14)5-8(7)12/h4-6,11-14H,3H2,1-2H3/t6-/m0/s1 YTALUFDCWBLHNU-LURJTMIESA-N 10 15 1 3 2,4,5-Trihydroxymethamphetamine (THMA-2 or THM) is a neurotoxin and a metabolite of MDMA. It has structural similarity to the dopamine neurotoxin 6-hydroxydopamine, and produces lasting serotonin deficits when administered centrally. European Journal of Pharmacology 221 2–3 1992 281–288 Long-term alteration in the central monoaminergic systems of the rat by 2,4,5-trihydroxyamphetamine but not by 2-hydroxy-4,5-methylenedioxymethamphetamine or2-hydroxy-4,5-methylenedioxyamphetamine Ikram Elayan James W. Gibb Glen R. Hanson Rodger L. Foltza Heng Keang Lima Michel Johnson 10.1016/0014-2999(92)90714-F 1358654 Chem Res Toxicol 2011 24 6 968–978 10.1021/tx2001459 3124246 Synthesis and Neurotoxicity Profile of 2,4,5-Trihydroxymethamphetamine and its 6-(N-Acetylcystein-S-yl) Conjugate Anne Neudörffer Melanie Mueller Claire-Marie Martinez Annis Mechan Una McCann George A. Ricaurte Martine Largeron 21557581 See also 2,4,5-Trihydroxyamphetamine (THA) 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine) 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine) 4-Hydroxy-3-methoxyamphetamine (HMA) 4-Hydroxy-3-methoxymethamphetamine (HMMA) Methyl-TMA-2 (N-methyl-2,4,5-trimethoxyamphetamine) References Category:Human pathological metabolites Category:Methamphetamines Category:Monoaminergic neurotoxins Category:Psychedelic drug metabolites