SDMA (drug)
Pharmaceutical compound
From Wikipedia, the free encyclopedia
SDMA, also known as 3,4-methylenethiooxy-N-methylamphetamine (3T-MDMA) or as MY100, is a putative entactogen of the phenethylamine and amphetamine families related to 3,4-methylenedioxy-N-methylamphetamine (MDMA).[1][2] It is the analogue of MDMA in which the oxygen atom at the 3 position within the 3,4-methylenedioxy substitution has been replaced with a sulfur atom to give a 1,3-benzoxathiole rather than 1,3-benzodioxole ring system.[1][2] The drug is also the N-methyl derivative of 3,4-methylenethiooxyamphetamine (SDA; 3T-MDA).[1] SDMA is of interest for potential therapeutic use.[1]
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| Other names | 3-Thio-MDMA; 3T-MDMA; MY100; MY-100; 3,4-Methylenethiooxy-N-methylamphetamine |
| Drug class | Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Stimulant |
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| Metabolites | SDA |
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| Formula | C11H15NOS |
| Molar mass | 209.31 g·mol−1 |
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Interactions
Pharmacology
Pharmacodynamics
Similarly to MDMA, SDMA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and a non-selective serotonin 5-HT2 receptor agonist.[1] However, SDMA was 11-fold more potent as a serotonin releaser, 19-fold more potent as a dopamine releaser, and 2-fold more potent as a norepinephrine releaser than MDMA in HEK293 cells in vitro.[1] In addition, it was about twice as potent as a serotonin 5-HT2A receptor agonist, whereas it showed similar agonistic potency as MDMA at the serotonin 5-HT2B and 5-HT2C receptors.[1] SDMA had similar activational efficacies at the serotonin 5-HT2 receptors as MDMA.[1] Due to its greater potency as a monoamine releasing agent, SDMA may be active at lower doses or concentrations than MDMA.[1]
SDMA produced hyperlocomotion and hyperthermia in rodents with similar profiles as MDMA.[1] However, SDMA did not produce rewarding effects in the conditioned place preference (CPP) paradigm unlike MDMA.[1] Hence, SDMA might have reduced misuse potential compared to MDMA.[1] As with MDMA, SDMA did not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and hence may not produce hallucinogenic effects in humans.[1] SDMA might be less cardiotoxic than MDMA due to having much greater monoamine-releasing potency but unaltered serotonin 5-HT2B receptor agonistic potency.[1]
Pharmacokinetics
The metabolism and metabolites of SDMA have been studied.[1] It showed more rapid clearance than MDMA in rodents and hence may have a shorter elimination half-life and/or duration.[1]
Chemistry
Synthesis
The chemical synthesis of SDMA has been described.[1]
Analogues
A notable analogue of SDMA is 4T-MMDA-2 (2-methoxy-4T-MDA), which was described by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved).[3] Other analogues of SDMA include SDA, MDMA, 5-MAPB, and 6-MAPBT, among others.[3][2]
History
SDMA was first mentioned in the scientific literature by 2013, but was only conceptually described at this time.[2] Subsequently, its synthesis and preclinical pharmacology were described by Nina Kastner and colleagues including Matthias Grill at MiHKAL in 2025.[1] In addition, SDMA was patented by Mydecine as a shorter-acting MDMA alternative in 2023.[4][5][6][7][8] Prodrugs of SDMA and/or related compounds have also been described.[9] The drug is of interest for potential therapeutic use, for instance treatment of post-traumatic stress disorder (PTSD).[1]