Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens.

NBOMe hallucinogens, such as 25I-NBOMe, are N-benzyl derivatives of 2C-X phenethylamines that bind with subnanomolar affinity to the 5-HT2A receptor and are highly potent in humans. Since 2010, online availability of these compounds has led to numerous toxicity cases and fatalities. A review of 51 reported cases indicates that rhabdomyolysis is a relatively common complication of severe NBOMe toxicity, potentially linked to seizures, hyperthermia, and vasoconstriction.

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Abstract

Serotonergic hallucinogens induce profound changes in perception and cognition. The characteristic effects of hallucinogens are mediated by 5-HT2A receptor activation. One class of hallucinogens are 2,5-dimethoxy-substituted phenethylamines, such as the so-called 2C-X compounds 2,5-dimethoxy-4-bromophenethylamine (2C-B) and 2,5-dimethoxy-4-iodophenethylamine (2C-I). Addition of an N-benzyl group to phenethylamine hallucinogens produces a marked increase in 5-HT2A-binding affinity and hallucinogenic potency. N-benzylphenethylamines ("NBOMes") such as N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (25I-NBOMe) show subnanomolar affinity for the 5-HT2A receptor and are reportedly highly potent in humans. Several NBOMEs have been available from online vendors since 2010, resulting in numerous cases of toxicity and multiple fatalities. This chapter reviews the structure-activity relationships, behavioral pharmacology, metabolism, and toxicity of members of the NBOMe hallucinogen class. Based on a review of 51 cases of NBOMe toxicity reported in the literature, it appears that rhabdomyolysis is a relatively common complication of severe NBOMe toxicity, an effect that may be linked to NBOMe-induced seizures, hyperthermia, and vasoconstriction.