5-HT2A/5-HT2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism.
Sebastian Leth-Petersen, Ida N Petersen, Anders A. Jensen, Christoffer Bundgaard, Mathias Bæk, Jan Kehler, Jesper L. Kristensen
ACS Chemical Neuroscience November 16, 2016 DOI: 10.1021/acschemneuro.6b00265 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Serotonin |
| Keywords | 5-ht2a receptor agonists Phenethylamines Hallucinogens Microsomal stability |
| Key points | All novel analogues of 25B-NBOMe had an intrinsic clearance above 1.3 L/kg/h, predictive of high first-pass metabolism. |
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-HT2A/5-HT2C 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-HT2 receptor agonist properties, all analogues had an intrinsic clearance above 1.3 L/kg/h predictive of high first-pass metabolism.
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Cites 6
- Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chemical Neuroscience March 19, 2014
- Serotonin 2A Receptor Agonist Binding in the Human Brain with [11C]Cimbi-36 Journal of Cerebral Blood Flow & Metabolism April 30, 2014
- Structure–activity relationships of serotonin 5‐HT2Aagonists Wiley Interdisciplinary Reviews Membrane Transport and Signalling February 28, 2012
- Metabolic Fate of Hallucinogenic NBOMes Chemical Research in Toxicology December 16, 2015
- Toxicities associated with NBOMe ingestion-a novel class of potent hallucinogens: a review of the literature. Psychosomatics 2015
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