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4-Methylthioamphetamine
Systematic (IUPAC) name
1-[4-(methylthio)phenyl]propan-2-amine
Identifiers
CAS number 14116-06-4
ATC code  ?
PubChem 151900
Chemical data
Formula C 10H15NS 
Mol. mass 181.299 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Class A / Schedule I
Routes  ?

4-Methylthioamphetamine (4-MTA) is an illicit drug and research chemical developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic highly selective serotonin releasing agent (SSRA) in animals.[1][2][3] It is distantly related to several other SSRAs, including MMAI, MDAI, and MDMAI.

Contents

Effects

4-MTA is a strong serotonin releaser similar to paramethoxyamphetamine (PMA), which can cause pronounced hyperthermia potentially resulting in organ failure and death.[4][5][6][7] The subjective effects of 4-MTA include prolonged stimulation, which, in contrast to other amphetamines, is accompanied by little sense of euphoria. 4-MTA is also an MAO-A inhibitor, which may explain its tendency to easily cause adverse effects, as MAOIs are not considered safe to use in conjunction with stimulants.[8][9][10]

History

It was developed by the research team led by David E. Nichols,[11] but was intended to be used only as an agent for laboratory research into the serotonin transporter protein, and Nichols was reportedly sad to see 4-MTA appear as a drug of abuse on the street.[12]

4-MTA was briefly sold in smartshops in the Netherlands, though was soon banned by the Dutch government after serious side-effects started to emerge. It was also briefly sold on the black market as MDMA during the late 1990s, mainly in the USA, but proved unpopular due to its high risk of severe side effects (several deaths were reported) and relative lack of positive euphoria.

Legality

4-MTA is currently a Class A drug in the United Kingdom although it has been suggested it be rescheduled as a Class B drug.[13]

See also

References

  1. ^ Huang X, Marona-Lewicka D, Nichols DE. (1992). "p-methylthioamphetamine is a potent new non-neurotoxic serotonin-releasing agent.". Eur J Pharmacol. 229 (1): 31–38. PMID 1473561.  
  2. ^ Li Q, Murakami I, Stall S, Levy AD, Brownfield MS, Nichols DE, Van de Kar LD. Neuroendocrine pharmacology of three serotonin releasers: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (MBDB), 5-methoxy-6-methyl-2-aminoindan (MMAi) and p-methylthioamphetamine (MTA). Journal of Pharmacology and Experimental Therapeutics. 1996 Dec;279(3):1261-7. PMID 8968349
  3. ^ Murphy J, Flynn JJ, Cannon DM, Guiry PJ, McCormack P, Baird AW, McBean GJ, Keenan AK. In vitro neuronal and vascular responses to 5-hydroxytryptamine: modulation by 4-methylthioamphetamine, 4-methylthiomethamphetamine and 3,4-methylenedioxymethamphetamine. European Journal of Pharmacology. 2002 May 24;444(1-2):61-7. PMID 12191583
  4. ^ Elliott SP. Fatal poisoning with a new phenylethylamine: 4-methylthioamphetamine (4-MTA). Journal of Analytical Toxicology. 2000 Mar;24(2):85-9. PMID 10732944
  5. ^ De Letter EA, Coopman VA, Cordonnier JA, Piette MH. One fatal and seven non-fatal cases of 4-methylthioamphetamine (4-MTA) intoxication: clinico-pathological findings. International Journal of Legal Medicine. 2001;114(6):352-6. PMID 11508803
  6. ^ Decaestecker T, De Letter E, Clauwaert K, Bouche MP, Lambert W, Van Bocxlaer J, Piette M, Van den Eeckhout E, Van Peteghem C, De Leenheer A. Fatal 4-MTA intoxication: development of a liquid chromatographic-tandem mass spectrometric assay for multiple matrices. Journal of Analytical Toxicology. 2001 Nov-Dec;25(8):705-10. PMID 11765028
  7. ^ Smets G, Bronselaer K, De Munnynck K, De Feyter K, Van de Voorde W, Sabbe M. Amphetamine toxicity in the emergency department. European Journal of Emergency Medicine. 2005 Aug;12(4):193-7. PMID 16034267
  8. ^ Carmo H, Remião F, Carvalho F, Fernandes E, de Boer D, dos Reys LA, de Lourdes Bastos M. 4-Methylthioamphetamine-induced hyperthermia in mice: influence of serotonergic and catecholaminergic pathways. Toxicology and Applied Pharmacology. 2003 Aug 1;190(3):262-71. PMID 12902197
  9. ^ Hurtado-Guzmán C, Fierro A, Iturriaga-Vásquez P, Sepúlveda-Boza S, Cassels BK, Reyes-Parada M. Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine. Journal of Enzyme Inhibition and Medicinal Chemistry. 2003 Aug;18(4):339-47. PMID 14567549
  10. ^ Carmo H, Brulport M, Hermes M, Oesch F, de Boer D, Remião F, Carvalho F, Schön MR, Krebsfaenger N, Doehmer J, Bastos Mde L, Hengstler JG. CYP2D6 increases toxicity of the designer drug 4-methylthioamphetamine (4-MTA). Toxicology. 2007 Jan 18;229(3):236-44. PMID 17156908
  11. ^ Huang X, Marona-Lewicka D, Nichols DE. p-methylthioamphetamine is a potent new non-neurotoxic serotonin-releasing agent. European Journal of Pharmacology. 1992 Dec 8;229(1):31-8. PMID 1473561
  12. ^ 4-MTA info on possible dangers - ecstasy.org
  13. ^ ""I think 4MTA, LSD and ecstasy probably shouldn't be Class A", from "Call for ecstasy to be downgraded", BBC News, Wednesday, 22 November 2006, 15:57 GMT

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