Top

Published in:

01-01-2017 | Short Communication

Simple regioisomeric differentiation of 2-, 3- and 4-methyl-α-pyrrolidinobutiophenones by gas chromatography–mass spectrometry using bromination

Authors: Hiroshi Fujii, Brian Waters, Kenji Hara, Masayuki Kashiwagi, Aya Matsusue, Shin-ichi Kubo

Published in: Forensic Toxicology | Issue 1/2017

Abstract

A simple method for the differentiation of three cathinone-type regioisomers, 2-, 3- and 4-methyl-α-pyrrolidinobutiophenone (MePBPs), using a bromination procedure was developed in this study. The bromination was performed in a vial where isomers of MePBP, iron(III) bromide, and liquid bromine were added. After excess bromine in the vial was evacuated and an alkaline solution was added, the compounds were extracted with n-hexane and analyzed by gas chromatography–mass spectrometry. This method is a useful way to differentiate among isomers of MePBPs using the differences in the number of peaks generated and the intensity ratio between peaks on the extracted ion chromatograms. This method seems to have great potential to be applied to regioisomer differentiation of other drugs.

Archer RP (2009) Fluoromethcathinone, a new substance of abuse. Forensic Sci Int 185:10–20CrossRefPubMed

Power JD, McGlynn P, Clarke K, McDermott SD, Kavanagh P, O’Brien J (2011) The analysis of substituted cathinones. Part 1: chemical analysis of 2-, 3- and 4-methylmethcathinone. Forensic Sci Int 212:6–12CrossRefPubMed

Kavanagh P, O’Brien J, Fox J, O’Donnell C, Christie R, Power JD, McDermott SD (2012) The analysis of substituted cathinones. Part 3. Synthesis and characterization of 2, 3-methylenedioxy substituted cathinones. Forensic Sci Int 216:19–28CrossRefPubMed

Abdel-Hay KM, DeRuiter J, Clark CR (2014) Regioisomeric bromodimethoxy benzyl piperazines related to the designer substance 4-bromo-2,5-dimethoxybenzylpiperazine: GC–MS and FTIR analysis. Forensic Sci Int 240:126–136CrossRefPubMed

Abdel-Hay KM, DeRuiter J, Clark CR (2014) Differentiation of the 1-(methylenedioxyphenyl)-2-piperazinopropanes and 1-(methoxyphenyl)-2-piperazinopropanones by GC-IRD and GC-MS. Forensic Sci Int 235:40–51CrossRefPubMed

Vaughn DL, Anderson KB (2006) Characterization of 1, 2, 3, 4-tetrabromocyclohexane isomers by GC-matrix isolation FTIR-MS. New J Chem 30:868–872CrossRef

Maher HM, Awad T, DeRuiter J, Clark CR (2012) GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: regioisomers related to 4-Br-2, 5-DMA (DOB). Drug Test Anal 4:591–600CrossRefPubMed

Tsujikawa K, Mikuma T, Kuwayama K, Miyaguchi H, Kanamori T, Iwata YT, Inoue H (2013) Identification and differentiation of methcathinone analogs by gas chromatography-mass spectrometry. Drug Test Anal 5:670–677CrossRefPubMed

Negishi S, Nakazono Y, Kanda K, Tsujikawa K, Kuwayama K, Kanamori T, Iwata YT, Miyamoto K, Kasuya F, Inoue H (2014) Differentiation of regioisomeric methylamphetamines by GC/MS (in Japanese with English abstract). Jpn J Forensic Sci Technol 19:111–119CrossRef

10.

Westphal F, Rösner P, Junge T (2010) Differentiation of regioisomeric ring-substituted fluorophenethylamines with product ion spectrometry. Forensic Sci Int 194:53–59CrossRefPubMed

11.

Westphal F, Junge T (2012) Ring positional differentiation of isomeric N-alkylated fluorocathinones by gas chromatography/tandem mass spectrometry. Forensic Sci Int 223:97–105CrossRefPubMed

12.

Zaitsu K, Miyagawa H, Sakamoto Y, Matsuda S, Tsuboi K, Nishioka H, Katagi M, Sato T, Tatsuno M, Tsuchihashi H, Suzuki K, Ishii A (2013) Mass spectrometric differentiation of the isomers of mono-methoxyethylamphetamines and mono-methoxydimethylamphetamines by GC–EI–MS–MS. Forensic Toxicol 31:292–300CrossRef

13.

Nakazono Y, Tsujikawa K, Kuwayama K, Kanamori T, Iwata YT, Miyamoto K, Kasuya F, Inoue H (2013) Differentiation of regioisomeric fluoroamphetamine analogs by gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry. Forensic Toxicol 31:241–250CrossRef

14.

Negishi S, Nakazono Y, Iwata YT, Kanamori T, Tsujikawa K, Kuwayama K, Yamamuro T, Miyamoto K, Yamashita T, Kasuya F, Inoue H (2015) Differentiation of regioisomeric chloroamphetamine analogs using gas chromatography–chemical ionization-tandem mass spectrometry. Forensic Toxicol 33:338–347CrossRefPubMedPubMedCentral

15.

Inoue H, Negishi S, Nakazono Y, Iwata YT, Tsujikawa K, Ohtsuru O, Miyamoto K, Yamashita T, Kasuya F (2016) Differentiation of ring-substituted bromoamphetamine analogs by gas chromatography–tandem mass spectrometry. Forensic Toxicol 34:125–132CrossRefPubMed

16.

McMurry JE (2003) Fundamentals of organic chemistry, 5th edn. Brooks/Cole, Pacific Grove

Title: Simple regioisomeric differentiation of 2-, 3- and 4-methyl-α-pyrrolidinobutiophenones by gas chromatography–mass spectrometry using bromination
Authors: Hiroshi Fujii
Brian Waters
Kenji Hara
Masayuki Kashiwagi
Aya Matsusue
Shin-ichi Kubo
Publication date: 01-01-2017
Publisher: Springer Japan
Published in: Forensic Toxicology / Issue 1/2017
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI: https://doi.org/10.1007/s11419-016-0329-6

At a glance: The ONWARDS insulin icodec trials

Springer Medicine

Simple regioisomeric differentiation of 2-, 3- and 4-methyl-α-pyrrolidinobutiophenones by gas chromatography–mass spectrometry using bromination

Abstract

At a glance: The ONWARDS insulin icodec trials

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 1/2017

Identification of (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (DP-UR-144) in a herbal drug product that was commercially available in the Tokyo metropolitan area

Rapid and ultrasensitive detection of botulinum neurotoxin serotype A1 in human serum and urine using single-molecule array method

Identification of exposure to toxic metals by means of segmental hair analysis: a case report of alleged chromium intoxication

Analytical differentiation of quinolinyl- and isoquinolinyl-substituted 1-(5-fluoropentyl)-1H-indole-3-carboxylates: 5F-PB-22 and its ten isomers

The Duquenois reaction revisited: mass spectrometric estimation of chromophore structures derived from major phytocannabinoids

Spectroscopic characterization and crystal structures of two cathinone derivatives: N-ethyl-2-amino-1-phenylpropan-1-one (ethcathinone) hydrochloride and N-ethyl-2-amino-1-(4-chlorophenyl)propan-1-one (4-CEC) hydrochloride