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Systematic (IUPAC) name
Clinical data
Legal status
CAS number 712-07-2
ATC code None
PubChem CID 12833
ChemSpider 12303
Chemical data
Formula C11H13ClN2
Mol. mass 208.687 g/mol

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known selective serotonin-dopamine releasing agents (SDRAs).[1] It has been investigated in animals as a potential treatment for cocaine dependence.[1] 5-Chloro-αMT has approximately 64-fold and 192-fold greater potency in evoking the release of serotonin and dopamine, respectively, versus norepinephrine.[1]

5-Chloro-αMT was not found to reliably produce intracranial self-administration in rats or substitute for cocaine in rats or monkeys.[1] It was determined through study of 5-chloro-αMT in rhesus monkeys that norepinephrine release has minimal or no influence on the abuse potential of monoamine releasing agents and that loss of norepinephrine release activity does not affect efficacy in reducing cocaine self-administration in SDRAs relative to serotonin-norepinephrine-dopamine releasing agents (SNDRAs) such as 1-(2-naphthyl)propan-2-amine (PAL-287).[1] However, SDRAs like PAL-542 would be expected to produce fewer side effects relative to SNDRAs, and thus would likely be comparatively more favorable in the treatment of cocaine dependence and other conditions.[1]

A related agent, 5-fluoro-α-methyltryptamine (5-fluoro-αMT) (also known as PAL-544), is a potent MAO-A inhibitor and 5-HT2A receptor agonist in addition to monoamine releaser,[1][2] and produces a strong head-twitch response in rats,[3] an effect which is highly correlated with psychedelic effects in humans.[4] Due to their close structural similarity, 5-chloro-αMT could possess similar properties, aspects of it which might limit its potential clinical utility.[5]

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  1. ^ a b c d e f g Banks ML, Bauer CT, Blough BE, et al. (June 2014). "Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys". Exp Clin Psychopharmacol 22 (3): 274–84. doi:10.1037/a0036595. PMID 24796848. 
  2. ^ Kinemuchi H, Arai Y (October 1986). "Selective inhibition of monoamine oxidase A and B by two substrate-analogues, 5-fluoro-alpha-methyltryptamine and p-chloro-beta-methylphenethylamine". Res. Commun. Chem. Pathol. Pharmacol. 54 (1): 125–8. PMID 3797802. 
  3. ^ Chairungsrilerd N, Furukawa K, Tadano T, Kisara K, Ohizumi Y (March 1998). "Effect of gamma-mangostin through the inhibition of 5-hydroxy-tryptamine2A receptors in 5-fluoro-alpha-methyltryptamine-induced head-twitch responses of mice". Br. J. Pharmacol. 123 (5): 855–62. doi:10.1038/sj.bjp.0701695. PMC 1565246. PMID 9535013. 
  4. ^ Corne SJ, Pickering RW (1967). "A possible correlation between drug-induced hallucinations in man and a behavioural response in mice". Psychopharmacologia 11 (1): 65–78. PMID 5302272. 
  5. ^ Yamamoto T, Ueki S (January 1981). "The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by hallucinogenic drugs". Pharmacol. Biochem. Behav. 14 (1): 89–95. PMID 6258178.