Misplaced Pages

5-Chloro-αET (code name PAL-526), or 5-chloro-AET, also known as 5-chloro-α-ethyltryptamine, is a serotonergic agent of the tryptamine and α-alkyltryptamine families. It is the derivative of α-ethyltryptamine (αET or AET) with a 5-chloro substitution. Analogues of 5-chloro-αET include 5-fluoro-αET, 5-chloro-αMT, and 5-fluoro-αMT.

The drug is known to act as a potent serotonin releasing agent (SRA) and relatively weak serotonin 5-HT_2A receptor near-full agonist. It shows negligible induction of norepinephrine and dopamine release but does act as a very weak dopamine reuptake inhibitor (DRI). 5-Chloro-αET's EC₅₀Tooltip half-maximal effective concentration and IC₅₀Tooltip half-maximal inhibitory concentration values are 33.2 nM for serotonin release, 249 nM (E_maxTooltip maximal efficacy = 87%) for serotonin 5-HT_2A receptor agonism (7.5-fold lower than for serotonin release), 1,838 nM for dopamine reuptake inhibition (55-fold lower than for serotonin release), and >10,000 nM for norepinephrine release. The monoamine release assays were performed in rat brain synaptosomes.

References

1. ^ Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (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. PMC 4211607. PMID 25193229. 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 Value is IC50 for uptake inhibition in nM.

This psychoactive drug-related article is a stub. You can help Misplaced Pages by expanding it.

• v
• t
• e

• 5-HT2A agonists
• Alpha-Alkyltryptamines
• Chloroarenes
• Serotonin receptor agonists
• Serotonin releasing agents
• Psychoactive drug stubs