Welcome to LookChem.com Sign In|Join Free
  • or
4-METHYLTHIOAMPHETAMIN, also known as 4-MTA, is a potent non-neurotonic serotonin-releasing agent and a selective, reversible monoamine oxidase-A (MAO-A) inhibitor. It is a methylthio analog of para-methoxyamphetamine (PMA), a hallucinogenic drug that has been scheduled in many countries. In animal models, the effects of 4-MTA are qualitatively and quantitatively indistinguishable from those of PMA. 4-METHYLTHIOAMPHETAMIN is intended for forensic applications.

14116-06-4

14116-06-4 Suppliers

This product is a nationally controlled contraband or patented product, and the Lookchem platform doesn't provide relevant sales information.

14116-06-4 Usage

Uses

Used in Forensic Applications:
4-METHYLTHIOAMPHETAMIN is used as a forensic tool for the detection and analysis of 4-METHYLTHIOAMPHETAMIN in cases related to illicit drug use and distribution. Its identification helps in understanding the prevalence and circulation of this substance in the drug market.
Used in Pharmaceutical Research:
4-METHYLTHIOAMPHETAMIN is used as a research compound for studying its effects on serotonin release and its potential as a monoamine oxidase-A (MAO-A) inhibitor. This research can contribute to the development of new treatments for various psychiatric and neurological disorders.
Used in Illicit Drug Market:
Although not a legitimate use, 4-METHYLTHIOAMPHETAMIN is used as a recreational drug in the form of "ecstasy" or "flatliners" on the illicit drug market.

Check Digit Verification of cas no

The CAS Registry Mumber 14116-06-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,1,1 and 6 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 14116-06:
(7*1)+(6*4)+(5*1)+(4*1)+(3*6)+(2*0)+(1*6)=64
64 % 10 = 4
So 14116-06-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H15NS/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3

14116-06-4Relevant academic research and scientific papers

In vitro neuronal and vascular responses to 5-hydroxytryptamine: Modulation by 4-methylthioamphetamine, 4-methylthiomethamphetamine and 3,4-methylenedioxymethamphetamine

Murphy, James E.J.,Flynn, James J.,Cannon, Dara M.,Guiry, Patrick J.,McCormack, Peter,Baird, Alan W.,McBean, Gethin J.,Keenan, Alan K.

, p. 61 - 67 (2002)

4-Methylthioamphetamine and 4-methylthiomethamphetamine are thioarylethylamines structurally related to 3,4-methylenedioxymethamphetamine (MDMA, 'Ecstasy'). This study compared effects of these agents and MDMA on 5-hydroxytryptamine (5-HT) signalling systems in the brain and vasculature in vitro. Both 4-methylthioamphetamine and 4-methylthiomethamphetamine (100 μM) reduced the rate of specific high affinity [3H]5-HT reuptake in isolated rat brain synaptosomes to 14% and 10% of control, respectively. The concentration required for half-maximal inhibition (IC50) of [3H]5-HT reuptake by 4-methylthioamphetamine (0.27 μM) was significantly lower (P3H]5-HT from synaptosomes, but were significantly less effective than MDMA at the concentrations tested (1-100 μM). In isolated rat aorta, a 15-min preincubation with 4-methylthioamphetamine or 4-methylthiomethamphetamine significantly reduced the maximal contraction (Emax) induced by 5-HT to 71% or 91% of control (P50) from 4.13 to 20.08 μM (Pmax or the EC50 of 5-HT-induced aortic contraction. It is concluded that both 4-methylthioamphetamine and 4-methylthiomethamphetamine are potent inhibitors of [3H]5-HT reuptake in the brain. Furthermore, unlike MDMA, they both directly inhibit 5-HT-mediated vascular contraction. These results suggest that these compounds may be potentially more harmful than MDMA in the context of human misuse.

Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted α-alkylthioamphetamines

Cloonan, Suzanne M.,Keating, John J.,Corrigan, Desmond,O'Brien, John E.,Kavanagh, Pierce V.,Williams, D. Clive,Meegan, Mary J.

experimental part, p. 4009 - 4031 (2010/08/06)

4-Methylthioamphetamine (4-MTA) is recognised as a 3,4-methylenedioxymethamphetamine (MDMA)-like drug of abuse. Such amphetamine-type drugs often contain byproducts of uncontrolled, illegal clandestine synthetic processes. We report the isolation and stru

Synthesis and serotonin transporter activity of sulphur-substituted α-alkyl phenethylamines as a new class of anticancer agents

Cloonan, Suzanne M.,Keating, John J.,Butler, Stephen G.,Knox, Andrew J.S.,Jorgensen, Anne M.,Peters, Guenther H.,Rai, Dilip,Corrigan, Desmond,Lloyd, David G.,Williams, D. Clive,Meegan, Mary J.

scheme or table, p. 4862 - 4888 (2010/01/16)

The discovery that some serotonin reuptake transporter (SERT) ligands have the potential to act as pro-apoptotic agents in the treatment of cancer adds greatly to their diverse pharmacological application. 4-Methylthioamphetamine (MTA) is a selective ligand for SERT over other monoamine transporters. In this study, a novel library of structurally diverse 4-MTA analogues were synthesised with or without N-alkyl and/or C-α methyl or ethyl groups so that their potential SERT-dependent antiproliferative activity could be assessed. Many of the compounds displayed SERT-binding activity as well as cytotoxic activity. While there was no direct correlation between these two effects, a number of derivatives displayed anti-tumour effects in lymphoma, leukaemia and breast cancer cell lines, showing further potential to be developed as possible chemotherapeutic agents.

S-oxidation products of alkylthioamphetamines

Rezende, Marcos Caroli,Nunez, Christian,Sepulveda-Boza, Silvia,Cassels, Bruce K.,Hurtado-Guzman, Claudio

, p. 2741 - 2750 (2007/10/03)

The preparation of the sulfoxides and the sulfones of two centrally active alkylthioamphetamine salts, (±)-1-(4-methylthiophenyl)-2-aminopropane hydrochloride (2) (MTA · HCl) and (±)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane hydrochloride (7) (AL