5-Chloro-DMT

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. It has been encountered as a novel designer drug.

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

5-Chloro-DMT acts as a serotonin receptor agonist. It is known to have affinity for and act as an agonist of the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors. 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. It exhibits lower efficacy in terms of serotonin 5-HT2A receptor calcium mobilization relative to the parent compound DMT.

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

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.

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.

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

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

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

• Substituted tryptamine

• 5-Chloro-DMT - Isomer Design