Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens

  • Adam L. HalberstadtEmail author
Part of the Current Topics in Behavioral Neurosciences book series (CTBN, volume 32)


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.


Head twitch response Locomotor activity Psychedelic Research chemical Serotonin syndrome 



This work was supported by grants from NIDA (R01 DA002925), NIMH (K01 MH100644), and the Veteran’s Affairs VISN 22 MIRECC. I would like to than Drs. Mark Geyer and Susan Powell, as well as Mr. Landon Klein, for their support and assistance with these studies.


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Authors and Affiliations

  1. 1.Department of PsychiatryUniversity of California San DiegoLa JollaUSA
  2. 2.Research Service, VA San Diego Healthcare SystemSan DiegoUSA

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