5-Chloro-DMT

Last updated

5-Chloro-DMT
5-Chloro-DMT.svg
Clinical data
Other names5-Chloro-N,N-dimethyltryptamine; 5-Chloro-DMT; 5-Cl-DMT
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 2-(5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H15ClN2
Molar mass 222.72 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C=C(C=C2)Cl
  • InChI=1S/C12H15ClN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3
  • Key:BXYDWQABVPBLBU-UHFFFAOYSA-N

5-Chloro-DMT, or 5-Cl-DMT, also known as 5-chloro-N,N-dimethyltryptamine, is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT) and other drugs such as 5-bromo-DMT and 5-fluoro-DMT. [1] It acts as a serotonin receptor agonist. [1] [2] [3] [4] The drug is known to have affinity for and to act as an agonist of the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors. [1] [5] [6] [7] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [1] [8] In addition, it produces hypolocomotion and hypothermia. [1] 5-Chloro-DMT was first described in the scientific literature by Benington and colleagues by 1960. [9] It has been encountered as a novel designer drug. [10] [11]

Contents

See also

References

  1. 1 2 3 4 5 Puigseslloses P, Nadal-Gratacós N, Fumàs B, Modenutti CP, Pottie E, Ortigosa JR, et al. (October 2025). "Neuropharmacology of halogenated DMT analogs: psychoplastogenic and antidepressant properties of 5-Br-DMT, a psychedelic derivative with low hallucinogenic potential". Molecular Psychiatry. doi:10.1038/s41380-025-03308-2. PMID   41120735.
  2. ↑ Benington F, Morin RD, Clark LC (September 1960). "Synthesis of some 5- and 6-chloro, 5-methyl, and 5,6,7-trimethyl derivatives of tryptamine". Journal of Organic Chemistry. 25 (9): 1542–1547. doi:10.1021/jo01079a020.
  3. ↑ Ibrahim MA, El-Alfy AT, Ezel K, Radwan MO, Shilabin AG, Kochanowska-Karamyan AJ, et al. (August 2017). "Marine Inspired 2-(5-Halo-1H-indol-3-yl)-N,N-dimethylethanamines as Modulators of Serotonin Receptors: An Example Illustrating the Power of Bromine as Part of the Uniquely Marine Chemical Space". Marine Drugs. 15 (8): 248. doi: 10.3390/md15080248 . PMC   5577603 . PMID   28792478.
  4. ↑ Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, et al. (May 2021). "Psychedelic-inspired drug discovery using an engineered biosensor". Cell. 184 (10): 2779–2792.e18. doi:10.1016/j.cell.2021.03.043. PMC   8122087 . PMID   33915107.
  5. ↑ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC   10029822 . PMID   36669875.
  6. ↑ Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, et al. (October 2023). "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". The Journal of Biological Chemistry. 299 (10) 105231. doi: 10.1016/j.jbc.2023.105231 . PMC   10570959 . PMID   37690691.
  7. ↑ Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, et al. (10 March 2023), Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery (PDF), doi: 10.21203/rs.3.rs-2667175/v1 , retrieved 18 March 2025
  8. ↑ Fumàs B, Nadal-Gratacós N, Pablo-Quesada A, Berzosa X, Camarasa J, Pubill D, et al. (2024). "5-halo-substituted DMT derivatives. Hallucinogenic response and early gene expression in mice". Neuroscience Applied. 3 104390. doi: 10.1016/j.nsa.2024.104390 .
  9. ↑ Benington F, Morin RD, Clark LC (1960). "Synthesis of Some 5- and 6-Chloro, 5-Methyl, and 5,6,7-Trimethyl Derivatives of Tryptamine". The Journal of Organic Chemistry. 25 (9): 1542–1547. doi:10.1021/jo01079a020. ISSN   0022-3263 . Retrieved 29 October 2025.
  10. ↑ "Analytical Report: 5-Cl-DMT" (PDF). Slovenia: Nacionalni Forenzični Laboratorij. July 2020.
  11. ↑ "5-Cl-DMT". АИПСИН[AIPSIN] (in Russian). Retrieved 29 October 2025.
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