Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
4-Methylthioamphetamine (4-MTA), also known as para-methylthioamphetamine (MTA), is a designer drug of the substituted amphetamine class developed in the 1990s by a team led by David E. Nichols, an American pharmacologist and medical chemist, at Purdue University. It acts as a non-neurotoxic highly selective serotonin releasing agent (SSRA) in animals.[2][3][4] 4-MTA is the methylthio derivative of amphetamine.
Use and effects
4-MTA is a strong serotonin releaser similar to para-methoxyamphetamine (PMA), which can cause pronounced hyperthermia potentially resulting in organ failure and death.[5][6][7][8][better source needed] Therefore, the major neuropharmacological effect is an increased release of serotonin, and the inhibition of serotonin uptake of monoamine oxidase A (MAO-A). The combination of the releasing of serotonin from neurons and the prevention of breaking this neurotransmitter down again, leads to dangerous serotonin syndrome. The serotonin syndrome is a hyper serotonergic state, which can become fatal and is a side effect of serotonergic drugs. The symptoms of serotonin syndrome caused by 4-MTA are described in the Report on the Risk Assessment of 4-MTA
Symptoms of the serotonin syndrome caused by 4-MTA
- Euphoria
- Drowsiness
- Sustained rapid eye movement
- Hyperreflexia – overreaction of the reflexes
- Agitation
- Restlessness
- Tachycardia – fast heart rate
- Headache
- Clumsiness
- Disorientation
- Intoxication – feeling drunk and dizzy
- Rigidity
- Rapid muscle contraction and relaxation in the ankle causing abnormal movements of the foot
- Muscle contraction and relaxation in the jaw
- Muscle twitching leading to hyperthermia
- Shivering
- High body temperature
- Sweating
- Altered mental status (including confusion and hypomania – a ‘happy drunk state’)
[9] Another effect is the increase of the secretion of several hormones, like adrenocorticotropic hormone (ACTH), corticosterone, prolactin, oxytocin, and renin induced by 4-MTA through stimulation of serotonergic neurotransmission. Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
There has been suggested that 4-MTA because of its slow onset of action, is more dangerous than other designer drugs. Users of the drug rapidly take another dose because they assume the first was inadequate; thus increasing the possibility of an overdose. (EMCDDA, 1999)
Today the knowledge about the effects of 4-MTA is narrow, because of very limited research and experimental data. The only four studies that are conducted show a weak effect on dopamine and noradrenaline. This study was executed with a single dose of 4-MTA, no study where the effect of multiple doses 4-MTA where researched exist up to date. Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Pharmacology
Pharmacodynamics
4-MTA is a monoamine releasing agent (MRA).[2][3][4][10] It was originally characterized as a selective serotonin releasing agent (SRA).[2][3] However, the drug was subsequently found to more weakly induce the release of dopamine as well.[4][10] 4-MTA shows a similar balance of monoamine reuptake inhibition as MDMA.[11]
In addition to its MRA activity, 4-MTA is a potent monoamine oxidase A (MAO-A) inhibitor.[12] Its IC50Tooltip half-maximal inhibitory concentration for MAO-A inhibition has been reported to be 250 nM.[12] The combination of serotonin release induction and MAOI activity is likely responsible for the severe serotonergic toxicity and hyperthermia that has occurred with 4-MTA.[11] Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
Buy (4-MTA) 4-Methylthioamphetamine Cas 14116-06-4
4-MTA shows significant affinity for the serotonin 5-HT2A and 5-HT2C receptors, but not for the serotonin 5-HT1A receptor.[13] Its affinities for these receptors have been reported to be 1,500 nM, 1,800 nM, and >18,000 nM, respectively.[13] 4-MTA is also a potent agonist of the mouse and rat trace amine-associated receptor 1 (TAAR1).[14][15] However, it is inactive at the human TAAR1 (EC50Tooltip half-maximal effective concentration > 10,000 nM).[14]
In animal drug discrimination tests, 4-MTA substitutes for MDMA but does not substitute for amphetamine, suggesting that it has entactogen-like but no stimulant-like effects.[11][16] Similarly, 4-MTA does not substitute for DOM in drug discrimination tests, suggesting that it lacks psychedelic-like effects.[16]
Pharmacokinetics
Recommendation (from TRS)
4-Methylthioamphetamine (CAS 14116-06-4) is also known as 4-MTA. Other names include “MK”, α-methyl-4-methylthiophenethylamine,”MTA”, p-methylthioamphetamine (p-MTA), “S5”, “Flatliner” and “The One and Only Dominator”. 4-MTA has one chiral centre and can exist as two enantiomers and a racemate. To date, only the racemic mixture has been reported to have been synthesized.
WHO review history
4-MTA has not been pre-reviewed by the Committee. However, the Committee decided to undertake a critical review of 4-MTA because it met the requirements for critical review specified in section 4.1, item (4).
Similarity to known substances and effects on the CNS
4-MTA is structurally similar to 4-methoxyamphetamine and is both a potent serotonin-releasing agent and a reversible inhibitor of monoamine oxidase A (MAO-A). Pharmacologically, it is similar to tenamfetamine (methylenedioxyamphetamine or MDA) and MDMA; studies suggest that 4-MTA is six times as potent as these substances in inhibiting 5-HT uptake.
Dependence potential
Drug discrimination studies in rats suggest that 4-MTA produces discriminative stimulus effects similar to MDMA. However, 4-MTA did not substitute for amphetamines, LSD or phencyclidine. Reports from the United Kingdom indicate that 4-MTA, like MDMA, is abused for its stimulant/euphoric effects (a “rush”).
Actual abuse and or/evidence of likelihood of abuse
4-MTA is abused mainly in Europe, where it appears to be part of the dance music culture. However, it is likely that its use is less widespread than it otherwise might be because of perceptions among users that the drug is stronger and more harmful than other “club drugs”, such as MDMA. Abuse of 4-MTA has resulted in a number of fatalities and hospital admissions. It appears that toxic effects can be produced directly from the drug, and that the presence of other drugs or alcohol mav exacerbate such effects.
Therapeutic usefulness
4-MTA has no recognized therapeutic use.
Recommendation
4-MTA is chemically and pharmacologically similar to 4-methoxyamphetamine, MDA and MDMA. It is a relatively new synthetic drug, and was seized for the first time in 1997. Although evidence of its actual abuse is available only in several European countries, recent seizures, including those of large quantities reported from a wider range of countries, suggest that trafficking and abuse of 4-MTA have become more widespread. On the basis of this information and its similarity to known MDA-type drugs, as well as drug discrimination studies in animals, it is estimated that 4-MTA is likely to be abused so as to constitute a public health and social problem, warranting its placement under international control. Taking into consideration that 4+-MTA has no recognized therapeutic use and that it has caused a number of fatalities, the Committee concluded that abuse of 4-MTA represents an especially serious risk to public health. The Committee therefore recommended that 4-MTA be placed in Schedule I of the 1971 Convention.
14116-06-4
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Basic information
- Product Name: 4-METHYLTHIOAMPHETAMIN
- Synonyms: 4-METHYLTHIOAMPHETAMIN;P 1882;p-MethylthioaMphetaMine;α-Methyl-4-(Methylthio)benzeneethanaMine;4-MTA;1-(4-methylsulfanylphenyl)propan-2-amine
- CAS NO:14116-06-4
- Molecular Formula: C10H15NS
- Molecular Weight: 181.3
- EINECS: N/A
- Product Categories: Amines;Aromatics;Sulfur & Selenium Compounds
- Mol File: 14116-06-4.mol
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Chemical Properties
- Melting Point: N/A
- Boiling Point: 289°C at 760 mmHg
- Flash Point: 128.6°C
- Appearance: /
- Density: 1.04g/cm3
- Vapor Pressure: 0.00226mmHg at 25°C
- Refractive Index: 1.568
- Storage Temp.: N/A
- Solubility: N/A
- PKA: 9.96±0.10(Predicted)
- CAS DataBase Reference: 4-METHYLTHIOAMPHETAMIN(CAS DataBase Reference)
- NIST Chemistry Reference: 4-METHYLTHIOAMPHETAMIN(14116-06-4)
- EPA Substance Registry System: 4-METHYLTHIOAMPHETAMIN(14116-06-4)
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Safety Data
- Hazard Codes: N/A
- Statements: N/A
- Safety Statements: N/A
- WGK Germany:
- RTECS:
- HazardClass: N/A
- PackingGroup: N/A
- Hazardous Substances Data: 14116-06-4(Hazardous Substances Data)
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.
14116-06-4Upstream product
14116-06-4Downstream Products
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
| SpectraBase Compound ID | KAttJdPmPy6 |
|---|---|
| InChI | InChI=1S/C10H15NS/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3 |
| InChIKey | OLEWMKVPSUCNLG-UHFFFAOYSA-N |
| Mol Weight | 181.3 g/mol |
| Molecular Formula | C10H15NS |
| Exact Mass | 181.092521 g/mol |
Attenuated Total Reflectance Infrared (ATR-IR) Spectrum
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| SpectraBase Spectrum ID | HvAhgXUlASZ |
|---|---|
| Name | 4-Methylthioamphetamine |
| Source of Sample | Alltech Associates, Inc., Grace Davison Discovery Sciences |
| Catalog Number | Free base of 01618 |
| Lot Number | Free base of 437 |
| Accessory | DurasamplIR II |
| CAS Registry Number | 14116-06-4 |
| Classification | Selective serotonin releasing agent |
| Compound Type | Pure |
| Copyright | Copyright © 2012-2025 John Wiley & Sons, Inc. All Rights Reserved. |
| Formula | C10H15NS |
| InChI | InChI=1S/C10H15NS/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3 |
| InChIKey | OLEWMKVPSUCNLG-UHFFFAOYSA-N |
| Instrument Name | Bio-Rad FTS |
| Sample Preparation Procedure | The HCl salt was dissolved in 0.5 ml water in a test tube, and 1 drop of 30% NaOH solution was added, causing the clear solution to turn cloudy white. 1 ml dichloromethane was added to the test tube, which was shaken thoroughly using a vortex mixer. The test tube was spun in a centrifuge to separate the organic and aqueous layers. The bottom organic layer was retrieved with a pipette and placed in another clean test tube. Most of the solvent was evaporated from the tube using a flow of nitrogen gas, and the remaining solution was used to create a film on the diamond window for ATR-IR. |
| Source of Spectrum | Forensic Spectral Research |
| Synonyms | 4-MTA 4-Methylthioamphetamine |
| Technique | ATR-Film (MeCl2) (DuraSamplIR II) |
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