4-methylthioamphetamine

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Structural formula
Structure of 4-methylthioamphetamine
General
Surname 4-methylthioamphetamine
other names
  • para -Methylthioamphetamine
  • 1- [4- (methylthio) phenyl] propan-2-amine
  • 4-methylthioamfetamine
  • 1- (4- (methylsulfanyl) phenyl) propan-2-ylazane ( IUPAC )
Molecular formula C 10 H 15 NS
External identifiers / databases
CAS number 14116-06-4
PubChem 151900
Wikidata Q230013
properties
Molar mass 181.30 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-methylthioamphetamine also para -Methylthioamphetamin called and mostly as 4-MTA abbreviated, is a psychoactive substance. In the drug scene , the substance is usually referred to as flatliners .

Legal situation

As a non-marketable narcotic drug, 4-MTA is subject to the Narcotics Act and was included in Appendix I of the BtMG by the emergency ordinance of October 7, 1998. As a designer drug, 4-methylthioamphetamine is banned on the market.

In Austria, any amount of 4MTA is prohibited for consumption and is therefore one of the non-prescription drugs according to BTMG - ANL. III.

Mode of action

4-MTA causes the release of serotonin and prevents its reuptake. In this effect it is very similar to the closely related 4-methoxyamphetamine . In addition, the enzyme monoamine oxidase A (MAO-A) is reversibly inhibited. When taken orally, the effects of 4-MTA begin after about an hour and last for about five to seven hours. 4-MTA is about three times more effective than MDMA ("Ecstasy"). The exact mechanism of action of 4-MTA is still largely unclear. The high is described by consumers as "gentle" and as a "relaxed state with a warm feeling of energy".

4-MTA poisoning occurs mainly because 4-MTA acts much more slowly than MDMA. The drug users then fatally assume that they have taken too low a dose or bad MDMA and increase the dose by taking more 4-MTA pills. In the case of the poisoning with 4-MTA caused in this way, extreme and life-threatening hyperthermia and hypertensive crises can be observed.

The abuse of 4-MTA led to a death of a 17-year-old in Saxony-Anhalt in the summer of 2000 .

However, some derivatives of 4-MTA are potential chemotherapeutic agents in the treatment of cancer .

Dangers of 4MTA

People who have never consumed 4MTA before can hardly assess the strong effect, especially since the qualitative perception changes little or not at all. In general, addictive substances that relate to quantitative perception are not correctly recognized despite excessive potency. Even users who previously used addictive substances such as alcohol , cannabis or MDMA can easily receive a dangerous overdose.

Interactions (high dangers due to interactions)

4MTA is always problematic for consumers who do not know the effect. This may lead to other drugs being taken at the same time, which creates a risk from this mixed use. There is a physical threat of exsiccosis , myoclonia , and delusions up to life-threatening pernicious disorders that require immediate emergency medical treatment.

Development history

4-Methylthioamphetamine was first synthesized in 1992 at Purdue University (Indiana) by a group led by the American chemist David E. Nichols (* 1944).

further reading

  • D. Blachut et al .: The analytical profile of some 4-methylthioamphetamine (4-MTA) homologues. In: Forensic Sci Int 192, 2009, pp. 98-114. PMID 19766415
  • H. Carmo et al .: CYP2D6 increases toxicity of the designer drug 4-methylthioamphetamine (4-MTA). In: Toxicology 229, 2007, pp. 236-244. PMID 17156908
  • ST Quinn et al: Blockade of noradrenaline transport abolishes 4-methylthioamphetamine-induced contraction of the rat aorta in vitro. In: Auton Autacoid Pharmacol 26, 2006, pp. 335-344. PMID 16968472
  • AH Ewald et al .: Studies on the metabolism and toxicological detection of the designer drug 4-methylthioamphetamine (4-MTA) in human urine using gas chromatography-mass spectrometry. In: J Chromatogr B Analyt Technol Biomed Life Sci 824, 2005, pp 123-131. PMID 16027051
  • RF Staack et al: Metabolism of designer drugs of abuse. In: Curr Drug Metab 6, 2005, pp. 259-274. PMID 15975043 (Review)
  • H. Carmo et al .: Comparative metabolism of the designer drug 4-methylthioamphetamine by hepatocytes from man, monkey, dog, rabbit, rat and mouse. In: Naunyn Schmiedebergs Arch Pharmacol 369, 2004, pp. 198-205. PMID 14676987
  • ME Soares et al: Simultaneous determination of amphetamine derivatives in human urine after SPE extraction and HPLC-UV analysis. In: Biomed Chromatogr 18, 2004, pp. 125-131. PMID 15039965
  • H. Carmo et al .: 4-Methylthioamphetamine-induced hyperthermia in mice: Influence of serotonergic and catecholaminergic pathways. In: Toxicol Appl Pharmacol 190, 2003, pp. 262-271. PMID 12902197
  • AR Winstock et al .: 4-MTA: a new synthetic drug on the dance scene. In: Drug Alcohol Depend 67, 2002, pp. 111-115. PMID 12095660
  • M. Dukat et al .: Effect of PMA optical isomers and 4-MTA in PMMA-trained rats. In: Pharmacol Biochem Behav 72, 2002, pp. 299-305. PMID 11900800
  • J. Murphy et al.: In vitro neuronal and vascular responses to 5-hydroxytryptamine: modulation by 4-methylthioamphetamine, 4-methylthiomethamphetamine and 3,4-methylenedioxymethamphetamine. In: Eur J Pharmacol 444, 2002, pp. 61-67. PMID 12191583
  • T. Decaestecker et al .: Fatal 4-MTA intoxication: development of a liquid chromatographic-tandem mass spectrometric assay for multiple matrices. In: J Anal Toxicol 25, 2001, pp. 705-710. PMID 11765028
  • PA De Letter et al .: One fatal and seven non-fatal cases of 4-methylthioamphetamine (4-MTA) intoxication: clinico-pathological findings. In: Int J Legal Med 114, 2001, pp. 352-356. PMID 11508803
  • SP Elliott: Analysis of 4-methylthioamphetamine in clinical specimens. In: Ann Clin Biochem 38, 2001, pp. 339-347. PMID 11471875
  • AJ Poortman and E. Lock: Analytical profile of 4-methylthioamphetamine (4-MTA), a new street drug. In: Forensic Sci Int 100, 1999, pp. 221-233. PMID 10423848
  • Q. Li ua: 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). In: J Pharmacol Exp Ther 279, 1996, pp. 1261-1267. PMID 8968349

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ juris: Annex I to the BtMG , accessed on November 21, 2009
  3. ↑ a b X. Huang et al: p-methylthioamphetamine is a potent new non-neurotoxic serotonin-releasing agent. In: Eur J Pharmacol 229, 1992, pp. 31-38. PMID 1473561
  4. ^ SP Elliot: Fatal poisoning with a new phenylethylamine. In: J Anal Toxicol 24, 2000, pp. 85-89. PMID 10732944
  5. ↑ J. Beike et al.: 4-MTA - a new amphetamine derivative. Lecture at the 9th spring conference of the Dt. Society for Forensic Medicine, Region North, Leipzig, May 5, 2000
  6. ^ EA De Letter et al .: Amphetamines as potential inducers of fatalities: a review in the district of Ghent from 1976-2004. In: Med Sci Law 46, 2006, pp. 37-65. PMID 16454462 (Review)
  7. ↑ SM Cloonan, JJ Keating, SG Butler, AJ Knox, AM Jørgensen, GH Peters, D. Rai, D. Corrigan, DG Lloyd, DC Williams, MJ Meegan: Synthesis and serotonin transporter activity of sulfur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents. In: Eur J Med Chem 44, 2009, pp. 4862-4888, PMID 19717215 .