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MDMA analogue From Wikipedia, the free encyclopedia
TDMA is a bioisosteric analogue of 3,4-methylenedioxy-N-methylamphetamine (MDMA) which was developed in an attempt to create an improved MDMA alternative for potential clinical use.[1] It is the analogue of MDMA in which the 1,3-benzodioxole ring has been replaced with a 2,1,3-benzothiadiazole ring.[1] ODMA and SeDMA are closely related analogues.[1] ODMA, TDMA, and SeDMA are releasing agents of serotonin, norepinephrine, and dopamine similarly to MDMA.[1] However, they are less potent and efficacious in activating the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors than MDMA and show differing and potentially improved metabolic and pharmacokinetic properties in comparison.[1] ODMA, TDMA, and SeDMA were first described in the scientific literature in June 2024.[1]
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| Clinical data | |
|---|---|
| Other names | Thiadiazolylmethamphetamine; Thiadiazolyl-N-methylamphetamine |
| Drug class | Serotonin–norepinephrine–dopamine releasing agent; Entactogen; Stimulant |
| Identifiers | |
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| CAS Number | |
| Chemical and physical data | |
| Formula | C10H13N3S |
| Molar mass | 207.30 g·mol−1 |
| 3D model (JSmol) | |
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MDMA and 3,4-methylenedioxyamphetamine (MDA) are well-known serotonergic neurotoxins that damage serotonergic neurons in the brain.[2][3][4][5][6] However, MDMA and MDA injected directly into the brain do not result in serotonergic neurotoxicity in rodents.[2][7][8] This suggests that peripherally formed metabolites of MDMA and MDA are the actual mediators of the neurotoxicity rather than MDMA and MDA themselves.[2][7][8] ODMA, TDMA, and SeDMA, with the exception of N-demethylation, do not share any of the phase I or phase II metabolic pathways of MDMA.[1] Notably, in contrast to MDMA, methylenedioxy ring opening and consequent formation of catechol metabolites, which have been linked with free radical generation, does not occur.[1] As a result, ODMA, TDMA, and SeDMA may not share the serotonergic neurotoxicity of MDMA and MDA.[1] However, more research is needed to assess this possibility.[1]
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