The drug is known to act as apotentserotonin releasing agent (SRA) and relatively weakserotonin5-HT2A receptor near-full agonist.[1] It shows negligible induction ofnorepinephrine anddopamine release but does act as a very weakdopamine reuptake inhibitor (DRI).[1] 5-Chloro-αET'sEC50Tooltip half-maximal effective concentration andIC50Tooltip half-maximal inhibitory concentration values are 33.2nM for serotonin release, 249nM (EmaxTooltip maximal efficacy = 87%) for serotonin 5-HT2A receptoragonism (7.5-fold lower than for serotonin release), 1,838nM for dopamine reuptake inhibition (55-fold lower than for serotonin release), and >10,000nM for norepinephrine release.[1] Themonoamine releaseassays were performed in rat brainsynaptosomes.[1]
^abcdefgBlough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, et al. (October 2014)."Alpha-ethyltryptamines as dual dopamine-serotonin releasers".Bioorg Med Chem Lett.24 (19):4754–4758.doi:10.1016/j.bmcl.2014.07.062.PMC4211607.PMID25193229.The racemic a-alkyl tryptamines 7a, 7b, 7c, 7d, 7e, and 7f were synthesized by nitro olefin formation followed by lithium ammonium hydride reduction (Scheme 2).32 [...] a-Ethylation of the 5-chloro and 5-fluoro substituted tryptamines, to form 7e and 7f respectively, also weakened NE release activity compared to their a-methyl analogs, but 7e flipped to become a weak DA uptake inhibitor. [...] In the a-ethyltryptamine series, the 5-chloro analog (7e) and 5-fluoro analog (7f) both weakened substantially as 5-HT2A agonists compared to their a-methyl- and non-alkylated tryptamine analogs (7b/7c and 4h/4j), with EC50 values of 249 nM and 246 nM, respectively. [...] Table 1 Comparison of the DAT, SERT, and NET-mediated release activity and 5-HT2A receptor activity of substituted tryptamines [...]d Value is IC50 for uptake inhibition in nM.
^Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144.ISBN978-0-85608-011-1.OCLC2176880.OL4850660M.[...] 5-chloro-, but not 6-chloro-, derivatives of α-methyl- and α-ethyl-tryptamine produced behavioural changes in animals (Whittle and Young, 1963); [...]
^Whittle BA, Young EH (July 1963). "The Synthesis and Pharmacological Activity of Some Chloro-α-alkyltryptamines".J Med Chem.6 (4):378–380.doi:10.1021/jm00340a009.PMID14184890.The synthesis of eight new monochloro analogs of a-methyl- and a-ethyltryptamines are described. These compounds were prepared by condensations of 4-, 5-, 6-, and 7-chloroindole-3-aldehydes with either nitroethane or nitropropane and subsequent reduction of the condensation products with lithium aluminum hydride. The tryptamines have been found to possess stimulant and anticonvulsant properties in rodents and to produce behavioral changes in cats. [...]
