Stereochemical Analysis of Methorphan Using (−)‐Menthyl Chloroformate

Abstract: Forensic laboratories around the world have seen an increase in the number of drug seizures containing methorphan. Levomethorphan is a narcotic and a controlled substance, and its enantiomer dextromethorphan is an antitussive agent used in over‐the‐counter medications. For the forensic analysis of seized drugs containing methorphan, it is important to report the stereochemical composition of the drug. Ideally, a method based on common forensic laboratory instrumentation is desirable. The use of the chiral derivatizing agent (?)‐menthyl chloroformate followed by routine gas chromatography–mass spectrometry analysis of the derivative was shown to successfully determine the stereochemical composition of methorphan. This approach was applied to a street seizure containing methorphan proving that it was pure dextromethorphan. The derivatives of dextro‐ and levomethorphan were subjected to mass spectroscopic and nuclear magnetic resonance analysis, which confirmed that the structure of the derivatives remained unchanged as a result of the derivatization process.     

Morbidity Involving the Hallucinogenic Designer Amines MDA and 2C‐I*

Abstract: A case is presented of a 39‐year‐old woman who suffered severe debilitation because of a hemorrhagic stroke in the context of substance abuse. The patient presented to the emergency room with rapidly diminishing mental status, hypertension, and vasoconstriction; her friends provided a history of ingestion of cocaine, 3,4‐methylenedioxymethamphetamine (MDMA), and 2C‐I, a novel designer amine. A multi‐targeted LC‐MS/MS method for sympathomimetic amines and related drugs in urine detected and quantified 2C‐I and MDA, while ruling out MDMA. The cause of the stroke was determined to be an underlying cerebrovascular abnormality called Moyamoya, secondary to substance abuse. In clinical laboratories, gas chromatography–mass spectrometry or liquid chromatography–tandem mass spectrometry (LC‐MS/MS) confirmation of a positive amphetamine immunoassay is usually directed only towards amphetamine, methamphetamine, MDMA and MDA. This report demonstrates the utility of testing for a wider menu of compounds using LC‐MS/MS in order to better characterize the prevalence and toxicities of novel amines such as 2C‐I.     

Validation of an LC–MS Method for the Detection and Quantification of BZP and TFMPP and their Hydroxylated Metabolites in Human Plasma and its Application to the Pharmacokinetic Study of TFMPP in Humans*

Abstract: An LC–MS method was developed for benzylpiperazine (BZP) and trifluoromethylphenylpiperazine (TFMPP), constituents of “party pills” or “legal herbal highs,” and their metabolites in human blood plasma. Compounds were resolved using a mixture of ammonium formate (pH 4.5, 0.01 M) and acetonitrile (flow rate of 1.0 mL/min) with a C18 column. Calibration curves were linear from 1 to 50 ng/mL (R² > 0.99); the lower limit of quantification (LLOQ) was 5 ng/mL; the accuracy was >90%; the intra‐ and interday relative standard deviations (R.S.D) were <5% and <10%, respectively. Human plasma concentrations of TFMPP were measured in blood samples taken from healthy adults (n = 6) over 24 h following a 60‐mg oral dose of TFMPP: these peaked at 24.10 ng/mL (±1.8 ng/mL) (C_max) after 90 min (T_max). Plasma concentrations of 1‐(3‐trifluoromethyl‐4‐hydroxyphenyl) piperazine peaked at 20.2 ng/mL (±4.6 ng/mL) after 90 min. TFMPP had two disposition phases (t_½ = 2.04 h (±0.19 h) and 5.95 h (±1.63 h). Apparent clearance (Cl/F) was 384 L/h (±45 L/h).     

Preliminary Studies into the Characterization of Chemical Markers of Decomposition for Geoforensics*

Abstract: In this paper, we report the results of our preliminary studies into chemical characterization of the fluids produced during decomposition in the absence of a soil matrix. Pig (Sus domestica) carcasses were used to model the human decomposition process in two separate locations, Western Australia (Perth) and Canada (Oshawa). Analysis involved simple dilution and filtration of the decomposition fluids followed by gas chromatography–mass spectrometry. Several previously unreported compounds were detected in the decomposition fluid samples during the trials, including benzeneacetic acid, benzenepropionic acid, 2‐piperidone, and isocaproic acid. Possible biosynthetic pathways for some of the compounds produced are proposed. Further research trials are required, particularly in the presence of soil matrices.