de Araujo Karen Rafaela Gonçalves, Fabris André Luis, Neves Júnior Luiz F, de Carvalho Ponce Júlio, Soares Alexandre Learth, Costa José Luiz, Yonamine Mauricio
School of Pharmaceutical Sciences, University of São Paulo, São Paulo, SP, 05508-000, Brazil.
Superintendence of the Technical-Scientific Police, Institute of Criminalistics, São Paulo, SP, 05507-060, Brazil.
Forensic Toxicol. 2023 Jan;41(1):142-150. doi: 10.1007/s11419-022-00646-6. Epub 2022 Oct 8.
MDA-19 or BZO-HEXOXIZID (N'-[(3Z)-1-(1-hexyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-benzohydrazide), in a more recent nomenclature, was first synthesized in 2008 as a selective type-2 cannabinoid receptor (CB2) agonist due to its potential to treat neuropathic pain. In Brazil, this substance was identified in a series of 53 apprehensions between September 2021 and February 2022. Nevertheless, what intrigues toxicologists is that BZO-HEXOXIZID does not exert significant type-1 cannabinoid receptor (CB1) agonism-which is responsible for the well-known psychoactivity of Δ-9-tetrahydrocannabinol. Thus, the objective of this work is to report the first apprehension and identification of BZO-HEXOXIZID in Brazil and to discuss pharmacologically the possible reasons why a CB2 agonist has been incorporated to the illicit market.
Suspected seized samples were sent to the Laboratory of the Scientific Police of the State of Sao Paulo. After the screening, samples were confirmed for the presence of BZO-HEXOXIZID using chromatography gas-mass spectrometry, Fourier-transform infrared spectroscopy and nuclear magnetic resonance techniques.
Of the 53 samples analyzed, 25 contained only BZO-HEXOXIZID and 28 with mixtures, of which 11 with the CB1 agonist ADB-BUTINACA. Other substances were found in association such as cocaine and caffeine.
BZO-HEXOXIZID was detected in a series of seized materials for the first time in Brazil. Nevertheless, there are still unanswered questions regarding the use of this selective CB2 agonist as a drug of abuse.
MDA - 19或BZO - HEXOXIZID(N'-[(3Z)-1-(1-己基)-2-氧代-1,2-二氢-3H-吲哚-3-亚基]-苯甲酰肼,在更新的命名法中)于2008年首次合成,作为一种选择性2型大麻素受体(CB2)激动剂,因其具有治疗神经性疼痛的潜力。在巴西,2021年9月至2022年2月期间的一系列53次查获中发现了这种物质。然而,毒理学家感兴趣的是,BZO - HEXOXIZID不会产生显著的1型大麻素受体(CB1)激动作用——而CB1激动作用是Δ-9-四氢大麻酚众所周知的精神活性的原因。因此,本研究的目的是报告巴西首次查获和鉴定BZO - HEXOXIZID,并从药理学角度讨论一种CB2激动剂被纳入非法市场的可能原因。
疑似查获的样本被送往圣保罗州科学警察局实验室。筛选后,使用气相色谱-质谱联用、傅里叶变换红外光谱和核磁共振技术确认样本中存在BZO - HEXOXIZID。
在分析的53个样本中,25个仅含有BZO - HEXOXIZID,28个含有混合物,其中11个含有CB1激动剂ADB - BUTINACA。还发现了其他相关物质,如可卡因和咖啡因。
巴西首次在一系列查获的材料中检测到BZO - HEXOXIZID。然而,关于这种选择性CB2激动剂作为滥用药物的使用仍有一些未解决的问题。