5-Chloro-DMT

Last updated

5-Chloro-DMT
5-Chloro-DMT.svg
5-Cl-DMT 3D.png
Clinical data
Other names5-Chloro-N,N-dimethyltryptamine; 5-Chloro-DMT; 5-Cl-DMT
Routes of
administration 		Unknown [1] [2]
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Pharmacokinetic data
Onset of action Unknown [1] [2]
Duration of action Unknown [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
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 psychedelic tryptamines such as 5-bromo-DMT and 5-fluoro-DMT. [3] It has been encountered as a novel designer drug. [2] [4] [1]

Contents

Use and effects

5-Chloro-DMT was not included or 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

Pharmacology

Pharmacodynamics

5-Chloro-DMT activities
TargetAffinity (Ki, nM)
5-HT1A 33 (Ki)
41 (EC50 Tooltip half-maximal effective concentration)
94% (Emax Tooltip maximal efficacy)
5-HT2A 134 (Ki)
310a (EC50)
45%a (Emax)
5-HT2C 55 (Ki)
22a (EC50)
81%a (Emax)
SERT 830 (Ki)
394 ( IC50 )
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes:a = Stimulation of IP1 Tooltip 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] 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

Analogues

Analogues of 5-chloro-DMT include 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

5-Chloro-DMT was first described in the scientific literature by Benington and colleagues by 1960. [14] It was encountered as a novel designer drug by 2020. [2] [4] [1]

See also

References

  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 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.
  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 21 October 2015.
  7. 1 2 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.
  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. ↑ 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.
  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. ↑ 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 .
  14. ↑ 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.
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