Forensic Chemistry of Substituted N-Benzylmethoxy (N-BOMe) Phenethylamines: Isomeric Designer Drugs Related to 25I-N-BOMe

As submitted by the proposer: A number of N-BOMe (N-benzylmethoxy-phenethylamine) drugs of abuse have appeared in illicit drug samples in recent years in the US and in Europe. These drugs represent a variety of aromatic ring substituents on the basic N-benzyl-phenethylamine molecular skeleton. In a number of these cases as many as 18 isomers of equal elemental composition can yield essentially identical mass spectra with potential chromatographic co-elution. This is the case for the 25C-, 25B- and 25I-NBOMe series of current N-BOMe drugs with 18 regioisomers for each of the three series. The possibility of chromatographic co-elution of compounds having identical mass spectra cannot be overlooked. It is unlikely that any current forensic identification of an N-BOMe drug could withstand a challenge/cross examination based on sound analytical principles and knowledge of the regioisomer issues in this drug series. Designer drug development in the N-benzyl-phenethylamine drugs will likely continue for many years. Future designer development will likely follow the pattern previously established in the amphetamine-like drugs. Even with the Controlled Substance Analog Act in place, the forensic chemist must identify the specific drug in order to know if it is an analogue of a controlled substance. Thus, there is an urgent need for a systematic and comprehensive investigation of the forensic chemistry of these N-benzyl-phenethylamine regioisomers. The broad objective of this research is to provide specificity, selectivity and reliability in the methods used to identify N-benzyl-phenethylamines. These goals will be achieved by development of methods allowing the forensic analyst to identify regioisomeric forms of substituted N-benzyl-phenethylamines among many compounds of mass spectral equivalence. The initial phase of this work will involve the synthesis of the halogenated (Cl, Br, and I) regioisomeric N-benzylmethoxy-dimethoxyphenethylamines (18 compounds in each halogenated series), a total of 54 compounds. Further extension will evaluate selected substituents such as monomethoxy, methylenedioxy, trifluoromethyl and variations of hydrocarbon chain and amino groups commonly encountered in designer drug modifications. The analytical phases include characterization using common forensic methods such as MS and IR on each compound. The chromatographic retention properties will be evaluated on a variety of stationary phases to establish structure-retention relationships. This project will significantly increase the forensic drug chemistry knowledge base for N-benzyl-phenethylamines by describing a unified approach for specific drug identification based on structure correlated analytical properties. These results will produce a more scientifically prepared forensic expert to interact at the interface of the legal system and the science of forensic drug chemistry. Note: This project contains a research and/or development component, as defined in applicable law. ca/ncf