N,N-Dimethyl-4-methylthioamphetamine

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−1
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).^[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 IC₅₀Tooltip 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]

References

^ ^a ^b 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.
^ ^a ^b ^c 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.
^ ^a ^b ^c ^d 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.
^ ^a ^b 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.
^ ^a ^b 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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[GuajardoVelásquezRaby2020-1] 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.

[Sotomayor-ZárateJaraAraos2014-2] 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.

[GobbiFunicelloGerstbrein2008-3] 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.

[Reyes-ParadaIturriaga-VasquezCassels2019-4] 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.

[Hurtado-GuzmánFierroIturriaga-Vásquez2003-5] 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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N,N-Dimethyl-4-methylthioamphetamine

See also

References

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