 | |
| Clinical data | |
|---|---|
| Other names | 4-MTMA;N-Methyl-4-methylthioamphetamine;N-Methyl-MTA; NMMTA; PAL-1063; PAL1063 |
| Drug class | Serotonin releasing agent;Monoamine oxidase inhibitor;Entactogen |
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| ChemSpider | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C11H17NS |
| Molar mass | 195.32 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
4-Methylthiomethamphetamine (4-MTMA; code namePAL-1063), also known asN-methyl-4-methylthioamphetamine (NMMTA), is amonoamine releasing agent (MRA) of theamphetamine family related to4-methylthioamphetamine (4-MTA) andN,N-dimethyl-4-methylthioamphetamine (DMMTA or 4-MTDMA).[1][2][3] Much less is known about 4-MTMA compared to 4-MTA.[4]
4-MTMA is known to act as apotentserotonin releasing agent (SRA).[1][3] ItsEC50Tooltip half-maximal effective concentration value for induction of serotonin release in rat brainsynaptosomes was 21 nM, whereasnorepinephrine anddopamine release were not reported.[3] In addition to its MRA activity, like 4-MTA, the drug has been found to act as a potentreversibleenzyme inhibitor ofmonoamine oxidase A (MAO-A).[4][5][6] It is about one-third as potent as 4-MTA as an MAO-A inhibitor.[5][6] ItsIC50Tooltip half-maximal inhibitory concentration value for MAO-A inhibition is 0.89 nM, whereas the values of 4-MTA are 0.13 nM for (+)-4-MTA and 2.04 nM for (–)-4-MTA.[5][6] Neither 4-MTA nor 4-MTMA inhibitedmonoamine oxidase B (MAO-B).[5][6] Potentmonoamine oxidase inhibition by amphetamines has been associated with dangerous and sometimes fataltoxicity in humans.[5][6]
In animaldrug discrimination tests, 4-MTA and 4-MTMA were found to generalize toMDMA.[4][2][7] 4-MTA substituted for theserotonergic agentPMMA, whereas 4-MTMA did not.[4][2][7] 4-MTA did not substitute for theserotonergic psychedelicDOM, whereas 4-MTMA was not assessed in DOM-trained animals.[4][2] Neither 4-MTA nor 4-MTMA substituted for thepsychostimulantsdextroamphetamine orcocaine.[4][2] It was concluded that 4-MTA and 4-MTMA show mainly MDMA-like effects in rodents.[4][2][7]
4-MTMA had not been identified as anillicit drug ordrug of misuse by 2004.[2][1] However, it is said to have been encountered as a noveldesigner drug by 2015.[8]
The present investigation examined these agents, and the N-monomethyl analog of 4-MTA (i.e., 4-MTMA), in tests of stimulus generalization (substitution) using a two-lever drug discrimination task with groups of rats trained to discriminate either the hallucinogen DOM [1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane], the stimulant cocaine, or the empathogen MDMA from vehicle. 4-MTA and its N-monomethyl analog 4-MTMA (ED50 = 0.8 mg/kg in both cases) substituted only for the MDMA stimulus, whereas 2C-T-7 (ED50 = 0.8 mg/kg) substituted only for the DOM stimulus. Thus, at the doses examined, 4-MTA and 4-MTMA appear to be MDMA-like agents, and 2C-T-7 seems best classified as a DOM-like hallucinogen.
Whereas pharmacological properties of 4-MTA are well described in the literature, much less is known about its N-methylated homologue, 4-methylthiomethamphetamine (4- MTMA). The 4-MTMA has been examined in the test of stimulus generalization using MDMA and PMMA-trained rats [11,12]. Because the stimulus generalization failed to occur with PMMA and instead the substitution took place upon the administration of 4-MTMA to MDMA-trained animals, the drug was considered to be a MDMA-like agent. Only one study was devoted to the biological activity of N-alkyl derivatives of 4-MTA with substituents other than N-methyl [16]. An important conclusion of this work was that all derivatives investigated, including 4-MTA and its N-methyl, Nethyl, N-propyl and N,N-dimethyl-homologues, acted as selective, reversible inhibitors of MAO-A and their potency decreased with the increasing size of the N-alkyl chain.
Relatively few amino group substituents have been studied in AMPH derivatives regarding their influence upon MAOI potency. In general terms, any N-substitution leads to a decrease in the activity of the compound as a MAOI-A. Thus, the N-methyl derivatives of AMPH, MTA, p-methoxyAMPH (PMA), and 3,4-methylenedioxyAMPH (MDA)— i.e. methamphetamine, NMMTA, PMMA, and MDMA respectively— have about one-third the inhibitory potency of their corresponding primary amine congeners (Scorza et al., 1997; Hurtado-Guzmán et al., 2003; Matsumoto et al., 2014; Santillo, 2014; Tables 1, 2, 4).
 | Thispsychoactive drug-related article is astub. You can help Wikipedia byexpanding it. |