SDMA (drug)

Last updated

SDMA
SDMA structure.svg
Clinical data
Other names3-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
ATC code
  • None
Pharmacokinetic data
Metabolites SDA
Identifiers
  • 1-(1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine
PubChem CID
Chemical and physical data
Formula C11H15NOS
Molar mass 209.31 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCS2)NC
  • InChI=1S/C11H15NOS/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
  • Key:FCMBKJAWTSTFFR-UHFFFAOYSA-N

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]

Contents

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 researchers 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] The drug is of interest for potential therapeutic use, for instance treatment of post-traumatic stress disorder (PTSD). [1]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 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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