Identification of Metabolite Biomarkers of the Designer Hallucinogen 25I-NBOMe in Mouse Hepatic Microsomal Preparations and Human Urine Samples Associated with Clinical Intoxication.
Justin L. Poklis, Sara K Dempsey, Kai Liu, Joseph K Ritter, Carl E. Wolf, Shijun Zhang, Alphonse Poklis
Journal of Analytical Toxicology October 1, 2015 DOI: 10.1093/jat/bkv079 (opens in new tab) via PubMed
Summary
AI-generated from the abstractFifteen metabolites of the designer hallucinogen 25I-NBOMe were identified in mouse liver microsomal preparations and in urine from two intoxicated patients. One patient's urine contained the parent drug and all fifteen metabolites; the other contained only three O-desmethyl metabolites. Two major urinary metabolites were synthesized. The authors recommend using β-glucuronidase hydrolysis before screening and using the metabolite M5 as the primary biomarker for detecting 25I-NBOMe use.
Study at a glance
| Characteristics | Laboratory study with human urine analysis Peer reviewed |
|---|---|
| Sample size | 2 |
| Population | Two patients intoxicated with 25I-NBOMe |
| Key finding | Fifteen 25I-NBOMe metabolites were identified; M5 is recommended as the primary biomarker for drug testing. |
Abstract
'NBOMe' (dimethoxyphenyl-N-[(2-methoxyphenyl)methyl]ethanamine) derivatives are a new class of designer hallucinogenic drugs widely available on the Internet. Currently, 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe) is the most popular abused derivative in the USA. There are little published data on the absorption, metabolism and elimination of 25I-NBOMe, or any of the other NBOMe derivatives. Therefore, there are no definitive metabolite biomarkers. We present the identification of fifteen 25I-NBOMe metabolites in phase I and II mouse hepatic microsomal preparations, and analysis of two human urine samples from 25I-NBOMe-intoxicated patients to test the utility of these metabolites as biomarkers of 25I-NBOMe use. The synthesis of two major urinary metabolites, 2-iodo-4-methoxy-5-[2-[(2-methoxyphenyl) methylamino]ethyl]phenol (2-O-desmethyl-5-I-NBOMe, M5) and 5-iodo-4-methoxy-2-[2-[(2-methoxyphenyl)methylamino]ethyl]phenol (5-O-desmethyl-2-I-NBOMe), is also presented. Seven phase II glucuronidated metabolites of the O-desmethyl or the hydroxylated phase I metabolites were identified. One human urine sample contained 25I-NBOMe as well as all 15 metabolites identified in mouse hepatic microsomal preparations. Another human urine sample contained no parent 25I-NBOMe, but was found to contain three O-desmethyl metabolites. We recommend β-glucuronidase enzymatic hydrolysis of urine prior to 25I-NBOMe screening and the use of M5 as the primary biomarker in drug testing.