25I-NBOMe ("N-Bomb")

"In 2010, a potent new synthetic hallucinogen known as “N-Bomb” emerged on the international recreational drug market [1]. First synthesized in 2003 by German chemist Ralph Heim, 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine, or 25I-NBOMe, was discovered to be a potent serotonin 2A (5-HT2A) receptor agonist [2]. In 2008, David Nichols furthered this work, creating a radiolabeled form of 25I-NBOMe for use as a high affinity, traceable 5-HT2A ligand, applicable to positron emission tomography and other research purposes [3]. By 2010, 25I-NBOMe began to appear on the Internet [2]. Soon, recreational user experiences were being posted on EROWID, a popular online psychoactive drug and plant library, which recently described NBOMes as “the defining psychedelics of 2013” [4].

"25I-NBOMe was the prototype and remains as one of this now expanding class of NBOMes, which are defined by the addition of a 2-methoxybenzyl (MeOB) functional group to the nitrogen of the phenylethylamine backbone (Fig. 1). While this 2-MeOB addition imparts an increased affinity for the 5-HT2A receptor, up to 16 times that of the well-described 2C-I amphetamine derivative, the impact of the specific halogen substitution on the benzene ring, which differentiates NBOMe variants, is less well-understood [5]. At least seven NBOMe variants seized from the recreational drug market have been described [6]. In November 2013, three, including 25I-NBOMe, 25C-NBOMe, and 25B-NBOMe were placed by the DEA in schedule I.