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N,N-Dimethyl-4-methylthioamphetamine

Clinical data
Other names	DMMTA; 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
IUPAC name N,N-dimethyl-1-(4-methylsulfanylphenyl)propan-2-amine
PubChem CID	46882974
ChemSpider	24657499
ChEMBL	ChEMBL1078835
Chemical and physical data
Formula	C12H19NS
Molar mass	209.35 g·mol
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC=C(C=C1)SC)N(C)C
InChI 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).

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)). However, EC₅₀ values for monoamine release by 4-MTDMA were not reported. 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).

In addition to its MRA activity, 4-MTDMA is a fairly potent monoamine oxidase A (MAO-A) inhibitor, with an IC₅₀Tooltip half-maximal inhibitory concentration of 2,100 nM. Potent monoamine oxidase inhibition by amphetamines has been associated with dangerous and sometimes fatal toxicity in humans.

See also

• Dimethylamphetamine

References

1. ^ 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. ^ 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. ^ 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. ^ 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. ^ 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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