SDA (drug)

Last updated

SDA
SDA.svg
Clinical data
Other names3-Thio-MDA; 3T-MDA; 3,4-Methylenethiooxyamphetamine
Drug class Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist; Entactogen; Stimulant; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 1-(1,3-benzoxathiol-5-yl)propan-2-amine
PubChem CID
ChemSpider
Chemical and physical data
Formula C10H13NOS
Molar mass 195.28 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCS2)N
  • InChI=1S/C10H13NOS/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
  • Key:OXGJJEZWSWXUNB-UHFFFAOYSA-N

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]

Contents

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 researchers at MiHKAL in 2025. [1] In addition, SDA was patented by Mydecine as a shorter-acting MDMA alternative in 2023. [4] [5] [6] [7] [8]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 Kastner N, Nadal-Gratacós N, Hemmer S, Alves da Silva L, McKee JL, Hell T, et al. (December 2025). "Next-Generation MDMA Analogue SDMA: Pharmacological and Metabolic Insights". ACS Chemical Neuroscience. 16 (24): 4725–4740. doi:10.1021/acschemneuro.5c00782. PMID   41329099.
  2. 1 2 3 4 Sáez-Briones P, Hernández A (September 2013). "MDMA (3,4-Methylenedioxymethamphetamine) Analogues as Tools to Characterize MDMA-Like Effects: An Approach to Understand Entactogen Pharmacology". Current Neuropharmacology. 11 (5): 521–534. doi:10.2174/1570159X11311050007. PMC   3763760 . PMID   24403876. Bioisosteric replacement of oxygen by sulfur has been shown to increase potency in a number of cases that bear some structural analogy to the molecules (Fig. 3B, [121]). A single such modification has been introduced in the dioxole ring of MMDA-2 (Fig. 2), and it seems reasonable to extend this concept based on the MDMA structure. As an extension of the latter, the study of isoxazoles and their dihydro derivatives (Figs. 3C and 3D) might be possible suitable templates for the development of novel MDMA-like molecules.
  3. 1 2 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. https://erowid.org/library/books_online/pihkal/pihkal167.shtml
  4. ↑ US US2024/0018117,Hoyer DW, Roscow RF, Ling R, Gao C,"Prodrug compounds of 3,4-methylenedioxymethamphetamine (MDMA) and methods of synthesizing the same",published 18 January 2024, assigned to Mydecine Innovations Group Inc.and Apoapsis Holdings, LLC
  5. ↑ US 11896577,Hoyer DW, Roscow RF, Ling R, Gao C,"Short-acting psychoactive compounds of the MDMA class",issued 13 February 2024, assigned to Mydecine Innovations Group Inc.and Apoapsis Holdings, LLC
  6. ↑ US 2023/0321034,Hoyer DW, Roscow RF, Ling R, Gao C,"Novel short-acting psychoactive compounds of the MDMA class",issued 13 February 2024, assigned to Mydecine Innovations Group Inc.and Apoapsis Holdings, LLC
  7. ↑ US 2024/0197679,Hoyer DW, Roscow RF, Ling R, Gao C,"Novel short-acting psychoactive compounds of the MDMA class",published 20 June 2024, assigned to Mydecine Innovations Group Inc.and Apoapsis Holdings, LLC
  8. ↑ WO 2023288013,Hoyer DW, Roscow RF,"Novel short-acting psychoactive compounds of the MDMA class",published 19 January 2023, assigned to Mydecine Innovations Group Inc.
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