5-Chloro-DMT
Psychedelic drug
From Wikipedia, the free encyclopedia
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]
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| Other names | 5-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] |
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| Chemical and physical data | |
| Formula | C12H15ClN2 |
| Molar mass | 222.72 g·mol−1 |
| 3D model (JSmol) | |
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Use and effects
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
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 33 (Ki) 41 (EC50) 94% (Emax) |
| 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 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
Analogues
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
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
Legal status
Canada
5-Chloro-DMT is not a controlled substance in Canada as of 2025.[17]
United States
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.