TDMA
Also called 1-(2,1,3-Benzothiadiazol-5-yl)-N-methylpropan-2-amine
Overview
TDMA is a bioisosteric analogue of 3,4-methylenedioxy-N-methylamphetamine (MDMA) which was developed in an attempt to create an improved MDMA alternative for potential clinical use. It is the analogue of MDMA in which the 1,3-benzodioxole ring has been replaced with a 2,1,3-benzothiadiazole ring. ODMA and SeDMA are closely related analogues. ODMA, TDMA, and SeDMA are releasing agents of serotonin, norepinephrine, and dopamine similarly to MDMA. However, they are less potent and efficacious in activating the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors than MDMA and show differing and potentially improved metabolic and pharmacokinetic properties in comparison. ODMA, TDMA, and SeDMA were first described in the scientific literature in June 2024.[1] WP
MDMA and 3,4-methylenedioxyamphetamine (MDA) are well-known serotonergic neurotoxins that damage serotonergic neurons in the brain. However, MDMA and MDA injected directly into the brain have been found to not produce serotonergic neurotoxicity in rodents. This suggests that peripherally formed metabolites of MDMA and MDA may be the actual mediators of the neurotoxicity rather than MDMA and MDA themselves. ODMA, TDMA, and SeDMA, with the exception of N-demethylation, do not share any of the phase I or phase II metabolic pathways of MDMA. Notably, in contrast to MDMA, methylenedioxy ring opening and consequent formation of catechol metabolites, which have been linked with free radical generation, does not occur. As a result, ODMA, TDMA, and SeDMA might not share the serotonergic neurotoxicity of MDMA and MDA. However, more research is needed to assess this possibility. Moreover, other studies have found that slow infusion of MDMA directly into the brain does produce signs of serotonergic neurotoxicity.[1–9] WP
Drug class
Serotonin–norepinephrine–dopamine releasing agent Entactogen Stimulant WP
From the Wikipedia article's infobox.
Chemistry
Mixing
For best safety practice, don't mix this drug with other stimulants.
Why: vasoconstriction, heart rate and blood pressure. PsychonautWiki says:
- “... may be dangerous to combine with other stimulants ... as they can increase one's heart rate and blood pressure to dangerous levels.” (PsychonautWiki, dangerous interactions table, "Stimulants" row, revision 148925)
- “Vasoconstriction can be described as a narrowing of the veins and blood vessels which results from a contraction of their muscular wall.” (PsychonautWiki, Vasoconstriction, revision 170337)
- “... it can also occur under the influence of traditional stimulants such as methamphetamine, caffeine, and MDMA.” (PsychonautWiki, Vasoconstriction, revision 170337)
- “Increased blood pressure is most commonly induced under the influence of heavy dosages of vasoconstricting compounds, such as traditional stimulants and stimulating psychedelics.” (PsychonautWiki, Increased blood pressure, revision 152273)
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.
User reports
Erowid erowid.org
ListingsBluelight bluelight.org
ListingsReddit reddit.com
ListingsPop culture
No references added yet.
Add a reference
Registered users can add songs, films, books, shows, games and art about this substance. Link a source that names the substance, such as the work's Wikipedia article, a review or an interview, not only the work itself. Entries are voted on and moderated like every other value on this page.
Opens when accounts launch.
Sources
- Journal / agency Alberto-Silva AS, Hemmer S, Bock HA, da Silva LA, Scott KR, Kastner N, Bhatt M, Niello M, Jäntsch K, Kudlacek O, Bossi E, Stockner T, Meyer MR, McCorvy JD, Brandt SD, Kavanagh P, Sitte HH. Bioisosteric analogs of MDMA: Improving the pharmacological profile?. J Neurochem. June 2024. doi:10.1111/jnc.16149 · PMID 38898705 · PMC11449655
- Journal / agency Costa G, Gołembiowska K. Neurotoxicity of MDMA: Main effects and mechanisms. Exp Neurol. January 2022. doi:10.1016/j.expneurol.2021.113894 · PMID 34655576
- Journal / agency Kostrzewa RM. Handbook of Neurotoxicity. 2022. doi:10.1007/978-3-031-15080-7_53
- Journal / agency Parrott AC. MDMA, serotonergic neurotoxicity, and the diverse functional deficits of recreational 'Ecstasy' users. Neurosci Biobehav Rev. September 2013. doi:10.1016/j.neubiorev.2013.04.016 · PMID 23660456
- Journal / agency Aguilar MA, García-Pardo MP, Parrott AC. Of mice and men on MDMA: A translational comparison of the neuropsychobiological effects of 3,4-methylenedioxymethamphetamine ('Ecstasy'). Brain Res. January 2020. doi:10.1016/j.brainres.2019.146556 · PMID 31734398
- Journal / agency Montgomery C, Roberts CA. Neurological and cognitive alterations induced by MDMA in humans. Exp Neurol. January 2022. doi:10.1016/j.expneurol.2021.113888 · PMID 34624331
- Journal / agency Monks TJ, Jones DC, Bai F, Lau SS. The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity. Ther Drug Monit. April 2004. doi:10.1097/00007691-200404000-00008 · PMID 15228153
- Journal / agency Esteban B, O'Shea E, Camarero J, Sanchez V, Green AR, Colado MI. 3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose. Psychopharmacology (Berl). March 2001. doi:10.1007/s002130000645 · PMID 11351932
- Other Ecstasy: The Complete Guide: A Comprehensive Look at the Risks and Benefits of MDMA. 2001
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.