2,4,5-Trihydroxymethamphetamine

2,4,5-Trihydroxymethamphetamine

Names
Preferred IUPAC name 5-[2-(Methylamino)propyl]benzene-1,2,4-triol
Other names THMA; THM
Identifiers
CAS Number	136706-32-6
3D model (JSmol)	Interactive image
ChemSpider	19983112
PubChem CID	131985
CompTox Dashboard (EPA)	DTXSID50897245
InChI 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
SMILES CNC(C)CC1=C(O)C=C(O)C(O)=C1
Properties
Chemical formula	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). Infobox references

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

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)

References

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.