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Serotonin–norepinephrine–dopamine releasing agent · Serotonin 5-HT2 receptor agonist · Entactogen · Stimulant · Serotonergic psychedelic · Hallucinogen

SDA

Also called 1-(1,3-benzoxathiol-5-yl)propan-2-amine

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Overview

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). 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. The drug is also the N-desmethyl analogue of 3,4-methylenethiooxy-N-methylamphetamine (SDMA; 3T-MDMA).[1][2] WP

Drug class

Serotonin–norepinephrine–dopamine releasing agent Serotonin 5-HT2 receptor agonist Entactogen Stimulant Serotonergic psychedelic Hallucinogen WP

From the Wikipedia article's infobox.

Pharmacology

Pharmacodynamics

Similarly to MDA, SDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and a non-selective serotonin 5-HT₂ receptor agonist. 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. 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. SDA had largely similar activational efficacies at the serotonin 5-HT₂ receptors as MDA. Due to its greater potency as a monoamine releasing agent, SDA may be active at lower doses or concentrations than MDA.[1] WP

SDA produced hyperlocomotion and hyperthermia in rodents and to a greater extent than SDMA or MDMA. However, SDA did not produce significant rewarding effects in the conditioned place preference (CPP) paradigm unlike MDMA but similarly to SDMA. Hence, SDA might have reduced misuse potential compared to other related drugs like MDMA. 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. Unlike SDMA and MDMA, SDA produced thigmotaxis in the open field test, an anxiety-like effect. SDA may be cardiotoxic due to serotonin 5-HT2B receptor agonism.[1] WP

Pharmacokinetics

The metabolism and metabolites of SDA have been studied. It showed more rapid clearance than MDA in rodents and hence may have a shorter elimination half-life and/or duration.[1] WP

History

History

SDA was first mentioned in the scientific literature by 2013, but was only conceptually described at this time. Subsequently, its synthesis and preclinical pharmacology were described by Nina Kastner and colleagues including Matthias Grill at MiHKAL in 2025. Prodrugs of SDA and/or related compounds have also been described.[1][2][3] WP

Chemistry

Formula
C10H13NOS PC
Molar mass (g/mol)
195.28 PC
IUPAC name (computed by PubChem)
1-(1,3-benzoxathiol-5-yl)propan-2-amine PC
SMILES
CC(CC1=CC2=C(C=C1)OCS2)N PC
InChIKey
OXGJJEZWSWXUNB-UHFFFAOYSA-N PC
PubChem CID
117285706
IUPAC name
1-(1,3-benzoxathiol-5-yl)propan-2-amine WP

Mixing

For best safety practice, don't mix this drug with other stimulants.

Why: vasoconstriction, heart rate and blood pressure. PsychonautWiki says:

Quotes from PsychonautWiki, CC BY-SA 4.0.

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

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Pop culture

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Sources

  1. Journal / agency Kastner N, Nadal-Gratacós N, Hemmer S, Alves da Silva L, McKee JL, Hell T, Cicalese G, Holy M, Kooti F, Jäntsch K, Baron R, Shacham N, Cuccurazzu B, Halberstadt AL, McCorvy JD, Stockner T, Meyer MR, López-Arnau R, Grill M, Sitte HH. Next-Generation MDMA Analogue SDMA: Pharmacological and Metabolic Insights. ACS Chemical Neuroscience. December 2025. doi:10.1021/acschemneuro.5c00782 · PMID 41329099
  2. Journal / agency Sáez-Briones P, Hernández A. MDMA (3,4-Methylenedioxymethamphetamine) Analogues as Tools to Characterize MDMA-Like Effects: An Approach to Understand Entactogen Pharmacology. Current Neuropharmacology. September 2013. doi:10.2174/1570159X11311050007 · PMID 24403876 · PMC3763760
  3. Other WIPO - Search International and National Patent Collections

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.