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SDMA (drug)

From Wikipedia, the free encyclopedia
Not to be confused withSeDMA.

Pharmaceutical compound
SDMA
Clinical data
Other names3-Thio-MDMA; 3T-MDMA; MY100; MY-100; 3,4-Methylenethiooxy-N-methylamphetamine
Drug classSerotonin–norepinephrine–dopamine releasing agent;Serotonin5-HT2 receptoragonist;Entactogen;Stimulant
ATC code
  • None
Pharmacokinetic data
MetabolitesSDA
Identifiers
  • 1-(1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine
PubChemCID
Chemical and physical data
FormulaC11H15NOS
Molar mass209.31 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 as3,4-methylenethiooxy-N-methylamphetamine (3T-MDMA) or asMY100, is a putativeentactogen of thephenethylamine andamphetamine families related to3,4-methylenedioxy-N-methylamphetamine (MDMA).[1][2] It is theanalogue of MDMA in which theoxygenatom at the 3 position within the 3,4-methylenedioxysubstitution has been replaced with asulfur atom to give a1,3-benzoxathiole rather than1,3-benzodioxolering system.[1][2] The drug is also theN-methylderivative of3,4-methylenethiooxyamphetamine (SDA; 3T-MDA).[1] SDMA is of interest for potential therapeutic use.[1]

Interactions

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See also:MDMA § Interactions,Trip killer § Antidotes of other hallucinogens, andMDMA/citalopram

Pharmacology

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Pharmacodynamics

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Similarly toMDMA, SDMA is aserotonin–norepinephrine–dopamine releasing agent (SNDRA) and anon-selectiveserotonin5-HT2 receptoragonist.[1] However, SDMA was 11-fold morepotent as aserotonin releaser, 19-fold more potent as adopamine releaser, and 2-fold more potent as anorepinephrine releaser than MDMA inHEK293cellsin vitro.[1] In addition, it was about twice as potent as a serotonin5-HT2A receptor agonist, whereas it showed similar agonistic potency as MDMA at the serotonin5-HT2B and5-HT2C receptors.[1] SDMA had similaractivationalefficacies at the serotonin 5-HT2 receptors as MDMA.[1] Due to its greater potency as amonoamine releasing agent, SDMA may be active at lower doses or concentrations than MDMA.[1]

SDMA producedhyperlocomotion andhyperthermia in rodents with similar profiles as MDMA.[1] However, SDMA did not producerewarding effects in theconditioned place preference (CPP) paradigm unlike MDMA.[1] Hence, SDMA might have reducedmisuse potential compared to MDMA.[1] As with MDMA, SDMA did not produce thehead-twitch response, a behavioral proxy ofpsychedelic effects, in rodents, and hence may not producehallucinogenic effects in humans.[1] SDMA might be lesscardiotoxic than MDMA due to having much greater monoamine-releasing potency but unaltered serotonin 5-HT2B receptor agonistic potency.[1]

Pharmacokinetics

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Themetabolism andmetabolites of SDMA have been studied.[1] It showed more rapidclearance than MDMA in rodents and hence may have a shorterelimination half-life and/orduration.[1]

Chemistry

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Synthesis

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Thechemical synthesis of SDMA has been described.[1]

Analogues

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A notableanalogue of SDMA is4T-MMDA-2 (2-methoxy-4T-MDA), which was described byAlexander Shulgin in his bookPiHKAL (Phenethylamines I Have Known and Loved).[3] Other analogues of SDMA includeSDA,MDMA,5-MAPB, and6-MAPBT, among others.[3][2]

History

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SDMA was first mentioned in thescientific literature by 2013, but was only conceptually described at this time.[2] Subsequently, itssynthesis andpreclinicalpharmacology were described by Nina Kastner and colleagues including Matthias Grill atMiHKAL in 2025.[1] In addition, SDMA waspatented byMydecine 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 ofpost-traumatic stress disorder (PTSD).[1]

See also

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References

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  1. ^abcdefghijklmnopqrsKastner 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.PMC 12715756.PMID 41329099.
  2. ^abcdSáez-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. ^abShulgin 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. 
  9. ^"WIPO - Search International and National Patent Collections".patentscope.wipo.int. Retrieved2025-12-23.

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