2,4,5-Trihydroxyamphetamine

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

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

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]

^ Elayan, I.; Gibb, J. W.; Hanson, G. R.; Lim, H. K.; Foltz, R. L.; Johnson, M. (May 1993). "Short-term effects of 2,4,5-trihydroxyamphetamine, 2,4,5-trihydroxymethamphetamine and 3,4-dihydroxymethamphetamine on central tryptophan hydroxylase activity". J Pharmacol Exp Ther. 265 (2): 813–8. PMID 8496826.
^ Elayan I, Gibb JW, Hanson GR, Lim HK, Foltz RL, Johnson M (1993). "Short-term effects of 2,4,5-trihydroxyamphetamine, 2,4,5-trihydroxymethamphetamine and 3,4-dihydroxymethamphetamine on central tryptophan hydroxyls activity". J Pharmacol Exp Ther. 265 (2): 813–818. PMID 8496826.

[MyUser_Ncbi.nlm.nih.gov_July_8_2015c-1] Elayan, I.; Gibb, J. W.; Hanson, G. R.; Lim, H. K.; Foltz, R. L.; Johnson, M. (May 1993). "Short-term effects of 2,4,5-trihydroxyamphetamine, 2,4,5-trihydroxymethamphetamine and 3,4-dihydroxymethamphetamine on central tryptophan hydroxylase activity". J Pharmacol Exp Ther. 265 (2): 813–8. PMID 8496826.

[2] Elayan I, Gibb JW, Hanson GR, Lim HK, Foltz RL, Johnson M (1993). "Short-term effects of 2,4,5-trihydroxyamphetamine, 2,4,5-trihydroxymethamphetamine and 3,4-dihydroxymethamphetamine on central tryptophan hydroxyls activity". J Pharmacol Exp Ther. 265 (2): 813–818. PMID 8496826.

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