5-HT2A/5-HT2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism

2016/08/26 by Sebastian Leth‐Petersen, Ida Nymann Petersen, Anders A. Jensen +4 · 1 citation
Psychology · Chemistry · Neuroscience · #Psychedelics and Drug Studies #Chemical synthesis and alkaloids #Neurotransmitter Receptor Influence on Behavior

paper · doi:10.1021/acschemneuro.6b00265

openalex publication_date 2016/08/26 · openalex created_date 2016/09/16 · openalex updated_date 2026/06/24

Abstract

The toxic hallucinogen 25B-NBOMe is very rapidly degraded by human liver microsomes and has low oral bioavailability. Herein we report on the synthesis, microsomal stability, and 5-HT 2A /5-HT 2C receptor profile of novel analogues of 25B-NBOMe modified at the primary site of metabolism. Although microsomal stability could be increased while maintaining potent 5-HT 2 receptor agonist properties, all analogues had an intrinsic clearance above 1.3 L/kg/h predictive of high first-pass metabolism.

Citations

• Psychedelics

Cited by

• 2C (psychedelics) [wikipedia]

Related

• Discovery of Highly Potent Serotonin 5-HT2 Receptor Agonists Inspired by Heteroyohimbine Natural Products
• Discovery ofNew N -H AporphineDerivatives As Brain-Penetrant Gq-Biased 5-HT2C Receptor Agonists and Dual 5-HT2C/5-HT2A Receptor Agonists
• Exploring a Druggable Hydrophobic Tunnel in the 5-HT2A Receptor with Potent Phenethylamines
• Investigation of the Structure–Activity Relationships of Psilocybin Analogues
• 25B‐NBOMe, a novel N‐2‐methoxybenzyl‐phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: Evidence of abuse potential