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2,4,5-Trihydroxyamphetamine

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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 theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

2,4,5-Trihydroxyamphetamine (THA) is aneurotoxin and a metabolite ofMDMA. It comes from the ring-hydroxylation of3,4-methylenedioxyamphetamine (MDA).

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

References

[edit]

^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.doi:10.1016/S0022-3565(25)38208-X.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.doi:10.1016/S0022-3565(25)38208-X.PMID 8496826.

v t e Monoaminergic neurotoxins
Dopaminergic	2′-CH₃-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 4-MMA 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 Methcathinone 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-HO-5-MeO-T 4,5-DHT 5-IAI 5-MAPB 5-MeO-DiPT 5,6-DHT 5,7-DHT 6,7-DHT αET ETAI Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP⁺ HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PBMA PCA PCMA PIA TAI
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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