2,4,5-Trihydroxyamphetamine

2,4,5-Trihydroxyamphetamine
Names
	Preferred IUPAC name 5-(2-Aminopropyl)benzene-1,2,4-triol
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 (THM) 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]

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. 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.

This neurotoxin article is a stub. You can help Wikipedia by expanding it.

[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.

[1]

[2]

v t e Neurotoxins
Animal toxins	Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx) Epibatidine Zetekitoxin AB Dendrotoxin
Bacterial	Botulinum toxin Tetanospasmin
Cyanotoxins	Anatoxin-a Guanitoxin BMAA Saxitoxin
Plant toxins	Aconitine Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin Thujone Volkensin Veratridine
Mycotoxins	Ibotenic acid Muscarine Muscimol
Pesticides	Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil Phenylsilatrane Chlorophenylsilatrane Sulfuryl fluoride Mipafox Schradan Dimefox
Nerve agents	Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VP VR VX GV EA-3990 EA-4056 T-1123 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) Fluorotabun Chinese VX EA-2192
Bicyclic phosphates	TBPS TBPO IPTBO
Cholinergic neurotoxins	Acetylcholine mustard Catecholine Choline mustard Ethylcholine mustard Hemicholinium mustard
Other	Dimethylcadmium Dimethylmercury Toxopyrimidine IDPN Tetraethyllead

See also[edit]

References[edit]