5-Chlorotryptamine (5-Cl-T; developmental code name PAL-441) is a serotonin receptor modulator and monoamine releasing agent of the tryptamine family. It is the 5-chloro derivative of tryptamine.
The drug shows affinity for the serotonin 5-HT1A, 5-HT2A, 5-HT6, and 5-HT7 receptors (Ki = 5.5–16nM, 317–889nM, 38nM, and 16nM, respectively). It acts as a potent agonist of the serotonin 5-HT1A receptor ( = 3,846nM) and of the 5-HT2A receptor ( = 4.11–145nM; = 109%). In addition, 5-chlorotryptamine is a serotonin releasing agent (SRA), with values for induction of monoamine release of 19.1nM for serotonin, 476nM for dopamine, and >10,000nM for norepinephrine in rat brain synaptosomes. Similarly to tryptamine and other simple amine-unsubstituted tryptamines, 5-chlorotryptamine was ineffective in producing the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.
Tryptamines without substitutions at the amine or alpha carbon, such as tryptamine, serotonin (5-hydroxytryptamine; 5-HT), and 5-methoxytryptamine (5-MeO-T), are known to be very rapidly metabolized and thereby inactivated by monoamine oxidase A (MAO-A) in vivo and to have very short elimination half-lives. However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.
The chemical synthesis of 5-chlorotryptamine has been described.
5-Chlorotryptamine was first described in the scientific literature by 1959.
See also Substituted tryptamine 5-Fluorotryptamine 5-Bromotryptamine 7-Chlorotryptamine 5-Chloro-DMT 5-Chloro-AMT
References
External links 5-Chlorotryptamine - Isomer Design