2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOME): A Harmful Hallucinogen Review. 2021

Katarzyna Kamińska, and Paweł Świt, and Kamilla Malek
Jagiellonian Centre for Experimental Therapeutics, Jagiellonian University in Krakow, Bobrzynskiego 14, Krakow 30-348, Poland.

NBOMes are N-benzylmethoxy derivatives of the 2C family compounds with N-2-methoxybenzyl moiety substituted by the methoxy group at the 2- and 5-position and the halogen group at the 4-position of the phenyl ring. These substances are a new class of potent serotonin 5-HT2A receptor agonist hallucinogens with potential harmful effects. The substitution with halogen of the already psychoactive phenethylamine produces a derivative (2C-I) with increased hallucinogenic effects. This class of hallucinogens has chemical structures very similar to natural hallucinogenic alkaloid mescaline and these are sold mainly via internet as a 'legal' alternative to other hallucinogenic drug-lysergic acid diethylamide (LSD). 25I-NBOMe is the first synthesized and one of the most common compound from NBOMes. Knowledge of pharmacological properties of 25I-NBOMe is very limited so far. There are only a few in vivo and in vitro so far published studies. The behavioral experiments are mainly related with the hallucinogenic effect of 25I-NBOMe while the in vitro studies concerning mainly the affinity for 5-HT2A receptors. The 25I-NBOMe Critical Review 2016 reported 51 non-fatal intoxications and 21 deaths associated with 25I-NBOMe across Europe. Case reports describe various toxic effects of 25I-NBOMe usage including tachycardia, hypertension, hallucinations, rhabdomyolysis, acute kidney injury and death. The growing number of fatal and non-fatal intoxication cases indicates that 25I-NBOMe should be considered as a serious danger to public health. This review aims to present the current state of knowledge on pharmacological effects and chemical properties of 25I-NBOMe and to describe reported clinical cases and analytical methods available for identification of this agent in biological material.

UI MeSH Term Description Entries
D010627 Phenethylamines A group of compounds that are derivatives of beta- aminoethylbenzene which is structurally and pharmacologically related to amphetamine. (From Merck Index, 11th ed) Phenylethylamines
D004118 Dimethoxyphenylethylamine A derivative of phenethylamine containing two substituent methoxy groups in the phenyl ring.
D005060 Europe The continent north of AFRICA, west of ASIA and east of the ATLANTIC OCEAN. Northern Europe,Southern Europe,Western Europe
D006213 Hallucinogens Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise. Hallucinogen,Hallucinogenic Agent,Hallucinogenic Drug,Hallucinogenic Substance,Psychedelic,Psychedelic Agent,Psychedelic Agents,Psychotomimetic Agent,Psychotomimetic Agents,Hallucinogenic Agents,Hallucinogenic Drugs,Hallucinogenic Substances,Psychedelics,Agent, Hallucinogenic,Agent, Psychedelic,Agent, Psychotomimetic,Agents, Hallucinogenic,Agents, Psychedelic,Agents, Psychotomimetic,Drug, Hallucinogenic,Drugs, Hallucinogenic,Substance, Hallucinogenic,Substances, Hallucinogenic
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D001596 Benzylamines Toluenes in which one hydrogen of the methyl group is substituted by an amino group. Permitted are any substituents on the benzene ring or the amino group. Phenylmethylamine,alpha-Aminotoluene,alpha Aminotoluene
D015198 Designer Drugs Drugs designed and synthesized, often for illegal street use, by modification of existing drug structures (e.g., amphetamines). Of special interest are MPTP (a reverse ester of meperidine), MDA (3,4-methylenedioxyamphetamine), and MDMA (3,4-methylenedioxymethamphetamine). Many drugs act on the aminergic system, the physiologically active biogenic amines. Customized Drug,Customized Drugs,Designer Drug,Drug, Customized,Drug, Designer,Drugs, Customized,Drugs, Designer

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