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,2,10H2,1H3Key: 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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. In another study, it was shown to significantly reduce striatal tyrosine hydroxylase activity.

References

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.

v t e Monoaminergic neurotoxins
Dopaminergic	2′-CH₃-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone 6,7-DHT ALDH inhibitors (e.g., disulfiram, methylmercury) Amphetamine Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP HPTP Mancozeb Maneb Mephedrone Methamphetamine Methylone MPP (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol Ziram
Noradrenergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4,5-THA 4,5-DHT 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine
Serotonergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 4,5-DHT 5-IAI 5-MAPB 5,6-DHT 5,7-DHT 6,7-DHT αET Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PCA PIA
Unsorted	5-HIAL RHPP RHPTP
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators

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