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NBOMes——麦角酸二乙酰胺的高效且有毒的替代物。

NBOMes-Highly Potent and Toxic Alternatives of LSD.

作者信息

Zawilska Jolanta B, Kacela Monika, Adamowicz Piotr

机构信息

Department of Pharmacodynamics, Medical University of Łódź, Łódź, Poland.

Department of Forensic Toxicology, Institute of Forensic Research, Kraków, Poland.

出版信息

Front Neurosci. 2020 Feb 26;14:78. doi: 10.3389/fnins.2020.00078. eCollection 2020.

DOI:10.3389/fnins.2020.00078
PMID:32174803
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7054380/
Abstract

Recently, a new class of psychedelic compounds named NBOMe (or 25X-NBOMe) has appeared on the illegal drug market. NBOMes are analogs of the 2C family of phenethylamine drugs, originally synthesized by Alexander Shulgin, that contain a -(2-methoxy)benzyl substituent. The most frequently reported drugs from this group are 25I-NBOMe, 25B-NBOMe, and 25C-NBOMe. NBOMe compounds are ultrapotent and highly efficacious agonists of serotonin 5-HT and 5-HT receptors (Ki values in low nanomolar range) with more than 1000-fold selectivity for 5-HT compared with 5-HT. They display higher affinity for 5-HT receptors than their 2C counterparts and have markedly lower affinity, potency, and efficacy at the 5-HT receptor compared to 5-HT or 5-HT. The drugs are sold as blotter papers, or in powder, liquid, or tablet form, and they are administered sublingually/buccally, intravenously, via nasal insufflations, or by smoking. Since their introduction in the early 2010s, numerous reports have been published on clinical intoxications and fatalities resulting from the consumption of NBOMe compounds. Commonly observed adverse effects include visual and auditory hallucinations, confusion, anxiety, panic and fear, agitation, uncontrollable violent behavior, seizures, excited delirium, and sympathomimetic signs such mydriasis, tachycardia, hypertension, hyperthermia, and diaphoresis. Rhabdomyolysis, disseminated intravascular coagulation, hypoglycemia, metabolic acidosis, and multiorgan failure were also reported. This survey provides an updated overview of the pharmacological properties, pattern of use, metabolism, and desired effects associated with NBOMe use. Special emphasis is given to cases of non-fatal and lethal intoxication involving these compounds. As the analysis of NBOMes in biological materials can be challenging even for laboratories applying modern sensitive techniques, this paper also presents the analytical methods most commonly used for detection and identification of NBOMes and their metabolites.

摘要

最近,一类名为NBOMe(或25X-NBOMe)的新型致幻化合物出现在非法毒品市场上。NBOMe是苯乙胺类2C家族药物的类似物,最初由亚历山大·舒尔金合成,含有一个-(2-甲氧基)苄基取代基。该类中最常被报道的药物是25I-NBOMe、25B-NBOMe和25C-NBOMe。NBOMe化合物是血清素5-HT和5-HT受体的超高效激动剂(Ki值在低纳摩尔范围内),与5-HT相比,对5-HT的选择性超过1000倍。它们对5-HT受体的亲和力高于其2C同类物,与5-HT或5-HT相比,在5-HT受体上的亲和力、效力和效能明显更低。这些药物以吸墨纸形式出售,或以粉末、液体或片剂形式存在,通过舌下/口腔、静脉内、鼻腔吸入或吸烟方式给药。自2010年代初引入以来,已经发表了许多关于食用NBOMe化合物导致临床中毒和死亡的报告。常见的不良反应包括视觉和听觉幻觉、意识模糊、焦虑、恐慌和恐惧、激动、无法控制的暴力行为、癫痫发作、兴奋谵妄以及拟交感神经体征,如瞳孔散大、心动过速、高血压、高热和多汗。还报告了横纹肌溶解、弥散性血管内凝血、低血糖、代谢性酸中毒和多器官功能衰竭。本综述提供了与使用NBOMe相关的药理特性、使用模式、代谢和预期效果的最新概述。特别强调了涉及这些化合物的非致命和致命中毒病例。由于即使对于采用现代灵敏技术的实验室来说,分析生物材料中的NBOMe也具有挑战性,本文还介绍了最常用于检测和鉴定NBOMe及其代谢物的分析方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2d7/7054380/6172d46004ee/fnins-14-00078-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2d7/7054380/2c73792b2547/fnins-14-00078-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2d7/7054380/6172d46004ee/fnins-14-00078-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2d7/7054380/2c73792b2547/fnins-14-00078-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2d7/7054380/6172d46004ee/fnins-14-00078-g002.jpg

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3
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