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Psychedelic drug

Pharmaceutical compound
5-Chloro-DMT
Clinical data
Other names5-Chloro-N,N-dimethyltryptamine; 5-Chloro-DMT; 5-Cl-DMT
Routes of
administration		Unknown[1][2]
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Pharmacokinetic data
Onset of actionUnknown[1][2]
Duration of actionUnknown[1][2]
Identifiers
  • 2-(5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H15ClN2
Molar mass222.72 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 psychedelic tryptamines such as 5-bromo-DMT and 5-fluoro-DMT.[3] It has been encountered as a novel designer drug.[2][4][1]

Use and effects

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5-Chloro-DMT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[5] No experience reports existed for the drug as of 2020.[2] In addition, its routes of administration and doses were unavailable as of 2020.[1] In any case, it is known that the closely structurally related psychedelics DMT, 5-bromo-DMT, and 5-MeO-DMT are all inactive orally.[6][5]

Interactions

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Pharmacology

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Pharmacodynamics

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5-Chloro-DMT activities
TargetAffinity (Ki, nM)
5-HT1A33 (Ki)
41 (EC50Tooltip half-maximal effective concentration)
94% (EmaxTooltip maximal efficacy)
5-HT2A134 (Ki)
310a (EC50)
45%a (Emax)
5-HT2C55 (Ki)
22a (EC50)
81%a (Emax)
SERT830 (Ki)
394 (IC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes: a = Stimulation of IP1Tooltip inositol phosphate formation. Sources: [7]

5-Chloro-DMT acts as a serotonin receptor agonist.[3][8][9][10] It is known to have affinity for and act as an agonist of the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors.[3][7][11][12] The drug shows higher affinity for the serotonin 5-HT1A receptor compared to unsubstituted dimethyltryptamine (DMT), with around 10-fold higher selectivity for this receptor over the serotonin 5-HT2A receptor.[3] It exhibits lower efficacy in terms of serotonin 5-HT2A receptor calcium mobilization relative to the parent compound DMT.[3]

The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, with intermediate potency among halogenated derivatives.[3][10][13][14][15] In addition, it produces hypolocomotion and hypothermia, effects that appear to be mediated through serotonin 5-HT1A receptor activation.[3]

5-Chloro-DMT demonstrates similar biased agonism patterns at the serotonin 5-HT2A receptor compared to other halogenated derivatives, showing higher potency and efficacy for β-arrestin2 recruitment relative to miniGαq recruitment, with bias factors comparable to serotonin.[3]

Chemistry

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Analogues

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Analogues of 5-chloro-DMT include 5-chlorotryptamine, dimethyltryptamine (DMT), 5-fluoro-DMT, 5-bromo-DMT, 5-TFM-DMT, 6-fluoro-DMT, bretisilocin (5-fluoro-MET), 5-chloro-AMT, 6-fluoro-AMT, 7-chloro-AMT, and 5,N,N-TMT, among others.[3]

History

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5-Chloro-DMT was first described in the scientific literature by Benington and colleagues by 1960.[16] It was encountered as a novel designer drug by 2020.[2][4][1]

Society and culture

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5-Chloro-DMT is not a controlled substance in Canada as of 2025.[17]

United States

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5-Chloro-DMT is not an explicitly controlled substance in the United States.[18] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

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References

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  1. 1 2 3 4 5 6 "5-Cl-DMT". АИПСИН [AIPSIN] (in Russian). Retrieved 29 October 2025.
  2. 1 2 3 4 5 6 Catalani V, Arillotta D, Corkery JM, Guirguis A, Vento A, Schifano F (2020). "Identifying New/Emerging Psychoactive Substances at the Time of COVID-19; A Web-Based Approach". Front Psychiatry. 11 632405. doi:10.3389/fpsyt.2020.632405. PMC 7900492. PMID 33633599.
  3. 1 2 3 4 5 6 7 8 9
  4. 1 2 "Analytical Report: 5-Cl-DMT" (PDF). Slovenia: Nacionalni Forenzični Laboratorij. July 2020.
  5. 1 2 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  6. ↑ Morris H, Wallach J (26 March 2013). "Sea DMT: God Molecule or Barnacle Repellent?". Vice. Archived from the original on 26 March 2013. Retrieved 2015.
  7. Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, etal. (April 2023). . . (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
  8. ↑ 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.
  9. ↑
  10. 1 2 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.
  11. ↑ 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.
  12. ↑ 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
  13. ↑
  14. ↑ 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.
  15. ↑ 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 17 March 2025
  16. ↑ 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.
  17. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  18. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
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