SDA (drug)
Pharmaceutical compound
From Wikipedia, the free encyclopedia
SDA, also known as 3,4-methylenethiooxyamphetamine (3T-MDA), is a putative entactogen and psychedelic drug of the phenethylamine and amphetamine families related to 3,4-methylenedioxyamphetamine (MDA).[1][2] It is the analogue of MDA 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-desmethyl analogue of 3,4-methylenethiooxy-N-methylamphetamine (SDMA; 3T-MDMA).[1]
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| Other names | 3-Thio-MDA; 3T-MDA; 3,4-Methylenethiooxyamphetamine |
| Drug class | Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Stimulant; Serotonergic psychedelic; Hallucinogen |
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| Formula | C10H13NOS |
| Molar mass | 195.28 g·mol−1 |
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Interactions
Pharmacology
Pharmacodynamics
Similarly to MDA, SDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and a non-selective serotonin 5-HT2 receptor agonist.[1] However, SDA was 16-fold more potent as a serotonin releaser, 16-fold more potent as a dopamine releaser, and 2-fold more potent as a norepinephrine releaser than MDA in HEK293 cells in vitro.[1] In addition, it was 2- to 3-fold more potent as an agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors than MDA.[1] SDA had largely similar activational efficacies at the serotonin 5-HT2 receptors as MDA.[1] Due to its greater potency as a monoamine releasing agent, SDA may be active at lower doses or concentrations than MDA.[1]
SDA produced hyperlocomotion and hyperthermia in rodents and to a greater extent than SDMA or MDMA.[1] However, SDA did not produce significant rewarding effects in the conditioned place preference (CPP) paradigm unlike MDMA but similarly to SDMA.[1] Hence, SDA might have reduced misuse potential compared to other related drugs like MDMA.[1] Similarly to findings with MDA, SDA produced the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and hence may produce hallucinogenic effects in humans.[1] Unlike SDMA and MDMA, SDA produced thigmotaxis in the open field test, an anxiety-like effect.[1] SDA may be cardiotoxic due to serotonin 5-HT2B receptor agonism.[1]
Pharmacokinetics
The metabolism and metabolites of SDA have been studied.[1] It showed more rapid clearance than MDA in rodents and hence may have a shorter elimination half-life and/or duration.[1]
Chemistry
Synthesis
The chemical synthesis of SDA has been described.[1]
Analogues
A notable analogue of SDA 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 SDA include SDMA, MDA, MDMA, 5-APB, 5-APDB, and 6-APBT, among others.[3][2]
History
SDA 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] Prodrugs of SDA and/or related compounds have also been described.[4]