2,4,5-Trihydroxyamphetamine

2,4,5-Trihydroxyamphetamine (THA) is a neurotoxin and a metabolite of MDMA. It comes from the ring-hydroxylation of 3,4-methylenedioxyamphetamine (MDA).

2,4,5-Trihydroxyamphetamine

Names
Preferred IUPAC name 5-(2-Aminopropyl)benzene-1,2,4-triol
Other names THA
Identifiers
CAS Number	136706-33-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL28225
ChemSpider	112205
PubChem CID	126234
UNII	C6JI2489W2
CompTox Dashboard (EPA)	DTXSID90897244
InChI InChI=1S/C9H13NO3/c1-5(10)2-6-3-8(12)9(13)4-7(6)11/h3-5,11-13H,2,10H2,1H3 Key: FWNNQQDQXAMXMK-UHFFFAOYSA-N
SMILES CC(N)CC1=C(O)C=C(O)C(O)=C1
Properties
Chemical formula	C9H13NO3
Molar mass	183.207 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

In one paper, it was shown to reduce hippocampal tryptophan hydroxylase activity by 54% after short-term treatment.^[1] In another study, it was shown to significantly reduce striatal tyrosine hydroxylase activity.^[2]

See also

• 2,4,5-Trihydroxymethamphetamine (THMA)
• 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine)
• 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine)
• 4-Hydroxy-3-methoxyamphetamine (HMA)
• 4-Hydroxy-3-methoxymethamphetamine (HMMA)