Open AccessDARK Classics in Chemical Neuroscience: NBOMes
Author(s) -
Christian B. M. Poulie,
Anders A. Jensen,
Adam L. Halberstadt,
Jesper L. Kristensen
Publication year - 2019
Publication title -
acs chemical neuroscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.158
H-Index - 69
ISSN - 1948-7193
DOI - 10.1021/acschemneuro.9b00528
Subject(s) - mescaline , psilocybin , lysergic acid , hallucinogen , lysergic acid diethylamide , adme , pharmacology , chemistry , phenethylamine , recreational use , 5 ht2a receptor , neuroscience , serotonin , psychology , receptor , 5 ht receptor , medicine , stereochemistry , biochemistry , biology , drug , recreation , ecology
N -Benzylphenethylamines, commonly known as NBOMes, are synthetic psychedelic compounds derived from the phenethylamine class of psychedelics (2C- X compounds), which originally have been derived from the naturally occurring alkaloid mescaline. Analogously to their parent compounds and other classical psychedelics, such as psilocybin and lysergic acid diethylamide (LSD), NBOMes are believed to exert their main pharmacological effects through activation of serotonin 2A (5-HT 2A ) receptors. Since their introduction as New Psychoactive Substances (NPSs) in 2010, NBOMes have been widely used for recreational purposes; this has resulted in numerous cases of acute toxicity, sometimes with lethal outcomes, leading to the classification of several NBOMes as Schedule I substances in 2013. However, in addition to their recreational use, the NBOMe class has yielded several important biochemical tools, including [ 11 C]Cimbi-36, which is now being used in positron emission tomography (PET) studies of the 5-HT 2A and 5-HT 2C receptors in the mammalian brain, and 25CN-NBOH, one of the most selective 5-HT 2A receptor agonists developed to date. In this Review, the history, chemistry, structure-activity relationships, ADME (absorption, distribution, metabolism, and excretion) properties, and safety profiles of NBOMes will be outlined and discussed.