title: Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens.
abstract: Serotonergic hallucinogens induce profound changes in perception and cognition. The characteristic effects of hallucinogens are mediated by 5-HT2Areceptor 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-HT2Areceptor 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.
authors.affiliation: Department of Psychiatry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0804, USA. ahalbers@ucsd.edu.|Research Service, VA San Diego Healthcare System, San Diego, CA, USA. ahalbers@ucsd.edu.
authors.forename: Adam L
authors.initials: AL
authors.lastname: Halberstadt
mesh_terms: D000818:Animals; D004118:Dimethoxyphenylethylamine / Q000009:adverse effects / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D005021:Ethylamines / Q000009:adverse effects / Q000737:chemistry / Q000494:pharmacology; D005334:Fever / Q000139:chemically induced; D006213:Hallucinogens / Q000009:adverse effects / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007462:Iodobenzenes / Q000009:adverse effects / Q000737:chemistry / Q000494:pharmacology; D051379:Mice; D044402:Receptor, Serotonin, 5-HT2A / Q000187:drug effects*; D044405:Receptor, Serotonin, 5-HT2C / Q000187:drug effects; D012206:Rhabdomyolysis / Q000139:chemically induced; D012640:Seizures / Q000139:chemically induced; D058826:Serotonin 5-HT2 Receptor Agonists / Q000009:adverse effects / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014661:Vasoconstriction / Q000187:drug effects
chemical_list: D004118:Dimethoxyphenylethylamine; D005021:Ethylamines; D006213:Hallucinogens; D007462:Iodobenzenes; C531104:N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine; D044402:Receptor, Serotonin, 5-HT2A; D044405:Receptor, Serotonin, 5-HT2C; D058826:Serotonin 5-HT2 Receptor Agonists; C554181:2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine; C521995:4-iodo-2,5-dimethoxy-beta-phenethylamine; C079321:2-(4-bromo-2,5-dimethoxyphenyl)ethylamine
keywords: Head twitch response; Locomotor activity; Psychedelic; Research chemical; Serotonin syndrome