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2,4,5-Trihydroxymethamphetamine

From Wikipedia, the free encyclopedia
2,4,5-Trihydroxymethamphetamine
Names
Preferred IUPAC name
5-[2-(Methylamino)propyl]benzene-1,2,4-triol
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=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
    Key: YTALUFDCWBLHNU-LURJTMIESA-N
  • CNC(C)CC1=C(O)C=C(O)C(O)=C1
Properties
C10H15NO3
Molar mass 197.234 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4,5-Trihydroxymethamphetamine (THMA) 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.[1][2]

See also

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References

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  1. ^ Ikram Elayan; James W. Gibb; Glen R. Hanson; Rodger L. Foltza; Heng Keang Lima; Michel Johnson (1992). "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". European Journal of Pharmacology. 221 (2–3): 281–288. doi:10.1016/0014-2999(92)90714-F. PMID 1358654.
  2. ^ Anne Neudörffer; Melanie Mueller; Claire-Marie Martinez; Annis Mechan; Una McCann; George A. Ricaurte; Martine Largeron (2011). "Synthesis and Neurotoxicity Profile of 2,4,5-Trihydroxymethamphetamine and its 6-(N-Acetylcystein-S-yl) Conjugate". Chem Res Toxicol. 24 (6): 968–978. doi:10.1021/tx2001459. PMC 3124246. PMID 21557581.