N,N-Dimethyl-4-methylthioamphetamine

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N,N-Dimethyl-4-methylthioamphetamine
N,N-Dimethyl-4-methylthioamphetamine.svg
Clinical data
Other namesDMMTA; N,N-Dimethyl-4-MTA; 4-Methylthio-N,N-dimethylamphetamine; 4-MTDMA; PAL-1062; PAL1062
Drug class Monoamine releasing agent; Monoamine oxidase inhibitor; Entactogen
Identifiers
  • N,N-dimethyl-1-(4-methylsulfanylphenyl)propan-2-amine
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C12H19NS
Molar mass 209.35 g·mol−1
3D model (JSmol)
  • CC(CC1=CC=C(C=C1)SC)N(C)C
  • InChI=1S/C12H19NS/c1-10(13(2)3)9-11-5-7-12(14-4)8-6-11/h5-8,10H,9H2,1-4H3
  • Key:NFRBJBFYUNQIQP-UHFFFAOYSA-N

N,N-Dimethyl-4-methylthioamphetamine (DMMTA or N,N-dimethyl-4-MTA; code name PAL-1062), also known as 4-methylthio-N,N-dimethylamphetamine (4-MTDMA), is a monoamine releasing agent (MRA) of the amphetamine family related to 4-methylthioamphetamine (4-MTA) and 4-methylthiomethamphetamine (4-MTMA or NMMTA). [1] [2] [3]

It has been described as an MRA of serotonin and dopamine that lacks induction of aortic contraction in vitro and hence may lack concomitant norepinephrine release (i.e., it may be a serotonin–dopamine releasing agent (SDRA)). [1] [2] [3] However, EC50 values for monoamine release by 4-MTDMA were not reported. [2] [3] 4-MTDMA is a partial releaser of serotonin rather than a full releaser, with a maximal efficacy for induction of serotonin release of either 25% or 50% relative to the full serotonin releasers MDMA or para-chloroamphetamine (PCA). [3]

In addition to its MRA activity, 4-MTDMA is a fairly potent monoamine oxidase A (MAO-A) inhibitor, with an IC50 Tooltip half-maximal inhibitory concentration of 2,100 nM. [4] [5] Potent monoamine oxidase inhibition by amphetamines has been associated with dangerous and sometimes fatal toxicity in humans. [4] [5]

See also

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References

  1. 1 2 Guajardo FG, Velásquez VB, Raby D, Núñez-Vivanco G, Iturriaga-Vásquez P, España RA, et al. (November 2020). "Pharmacological Characterization of 4-Methylthioamphetamine Derivatives". Molecules. 25 (22): 5310. doi: 10.3390/molecules25225310 . PMC   7696343 . PMID   33203055.
  2. 1 2 3 Sotomayor-Zárate R, Jara P, Araos P, Vinet R, Quiroz G, Renard GM, et al. (May 2014). "Improving amphetamine therapeutic selectivity: N,N-dimethyl-MTA has dopaminergic effects and does not produce aortic contraction". Basic Clin Pharmacol Toxicol. 114 (5): 395–399. doi:10.1111/bcpt.12168. PMID   24314229.
  3. 1 2 3 4 Gobbi M, Funicello M, Gerstbrein K, Holy M, Moya PR, Sotomayor R, et al. (June 2008). "N,N-dimethyl-thioamphetamine and methyl-thioamphetamine, two non-neurotoxic substrates of 5-HT transporters, have scant in vitro efficacy for the induction of transporter-mediated 5-HT release and currents". J Neurochem. 105 (5): 1770–1780. doi:10.1111/j.1471-4159.2008.05272.x. PMC   4502523 . PMID   18248615.
  4. 1 2 Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi: 10.3389/fphar.2019.01590 . PMC   6989591 . PMID   32038257.
  5. 1 2 Hurtado-Guzmán C, Fierro A, Iturriaga-Vásquez P, Sepúlveda-Boza S, Cassels BK, Reyes-Parada M (August 2003). "Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine" (PDF). J Enzyme Inhib Med Chem. 18 (4): 339–47. doi:10.1080/1475636031000118437. PMID   14567549.


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