Structure via PubChem · Public domain (PubChem)
4-methylthioamphetamine
Sign in to saveAlso known as 4-MTA
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. 4-MTA is the methylthio derivative of amphetamine.
Chemical data
- Formula
- C10H15NS
- Molecular weight
- 181.3 g/mol
- IUPAC name
- 1-(4-methylsulfanylphenyl)propan-2-amine
- SMILES
- CC(CC1=CC=C(C=C1)SC)N
- InChIKey
- OLEWMKVPSUCNLG-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 51.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
52 papers- Pharmacological Characterization of 4-Methylthioamphetamine Derivatives.Molecules (Basel, Switzerland) · 2020
- Analysis of 4-methylthioamphetamine in clinical specimens.Annals of clinical biochemistry · 2001
- Synthesis of 4-methyl-5-arylpyrimidines and 4-arylpyrimidines: route specific markers for the Leuckardt preparation of amphetamine, 4-methoxyamphetamine, and 4-methylthioamphetamine.Forensic science international · 2001
- In vitro neuronal and vascular responses to 5-hydroxytryptamine: modulation by 4-methylthioamphetamine, 4-methylthiomethamphetamine and 3,4-methylenedioxymethamphetamine.European journal of pharmacology · 2002
- Fatal poisoning with a new phenylethylamine: 4-methylthioamphetamine (4-MTA).Journal of analytical toxicology · 2000
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 181.093
Show 4 more facts
- Commons category
- 4-Methylthioamphetamine
- canonical SMILES
- CC(CC1=CC=C(C=C1)SC)N
- chemical formula
- C₁₀H₁₅NS
- subject has role
- stimulant
Sources (2)
via Wikidata · CC0
~9 min read
Encyclopedic overview
13 sectionsContents
- Use and effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Metabolism
- Chemistry
- History
- First appearance
- Development
- Use and availability
- See also
- References
- External links
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. 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. 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
Excerpted from Wikipedia’s “4-methylthioamphetamine” article, available under the CC BY-SA 4.0 licence.