Top

Published in:

Open Access 01-07-2016 | Short Communication

Successful quantification of 4′-methyl-α-pyrrolidinohexanophenone (MPHP) in human urine using LC–TOF-MS in an autopsy case

Authors: Kaori Shintani-Ishida, Yasuhiro Kakiuchi, Hiroshi Ikegaya

Published in: Forensic Toxicology | Issue 2/2016

Abstract

The toxicological detection of the new synthetic cathinone 4′-methyl-α-pyrrolidinohexanophenone (MPHP) in urine samples has been impossible, because much of MPHP is metabolized before its excretion into urine. In this study, we successfully quantified unmetabolized MPHP in urine of an autopsy case using a sensitive method by liquid chromatography–time-of-flight-mass spectrometry. The quantification method showed good linearity in the range of 1.00–100 ng/mL, and the limit of detection was 0.5 ng/mL in human urine. In the autopsy case, the concentrations of MPHP in urine, plasma, and liver tissue samples were determined to be 60.1, 32.9 ng/mL, and 63.1 ng/g, respectively.

Zaitsu K, Katagi M, Tsuchihashi H, Ishii A (2014) Recently abused synthetic cathinones, alpha-pyrrolidinophenone derivatives: a review of their pharmacology, acute toxicity, and metabolism. Forensic Toxicol 32:1–8CrossRef

Kelly JP (2011) Cathinone derivatives: a review of their chemistry, pharmacology and toxicology. Drug Test Anal 3:439–453CrossRefPubMed

Westphal F, Junge T, Rosner P, Fritschi G, Klein B, Girreser U (2007) Mass spectral and NMR spectral data of two new designer drugs with an alpha-aminophenone structure: 4′-methyl-alpha-pyrrolidinohexanophenone and 4′-methyl-alpha-pyrrolidinobutyrophenone. Forensic Sci Int 169:32–42CrossRefPubMed

Uchiyama N, Matsuda S, Kawamura M, Shimokawa Y, Kikura-Hanajiri R, Aritake K, Urade Y, Goda Y (2014) Characterization of four new designer drugs, 5-chloro-NNEI, NNEI indazole analog, alpha-PHPP and alpha-POP, with 11 newly distributed designer drugs in illegal products. Forensic Sci Int 243:1–13CrossRefPubMed

Kalant H (2001) The pharmacology and toxicology of “ecstasy” (MDMA) and related drugs. Can Med Assoc J 165:917–928

Simmler LD, Buser TA, Donzelli M, Schramm Y, Dieu LH, Huwyler J, Chaboz S, Hoener MC, Liechti ME (2013) Pharmacological characterization of designer cathinones in vitro. Br J Pharmacol 168:458–470CrossRefPubMed

Sauer C, Hoffmann K, Schimmel U, Peters FT (2011) Acute poisoning involving the pyrrolidinophenone-type designer drug 4′-methyl-alpha-pyrrolidinohexanophenone (MPHP). Forensic Sci Int 208:e20–e25CrossRefPubMed

Springer D, Peters FT, Fritschi G, Maurer HH (2003) New designer drug 4′-methyl-alpha-pyrrolidinohexanophenone: studies on its metabolism and toxicological detection in urine using gas chromatography-mass spectrometry. J Chromatogr B 789:79–91CrossRef

Peters FT, Dragan CA, Kauffels A, Schwaninger AE, Zapp J, Bureik M, Maurer HH (2009) Biotechnological synthesis of the designer drug metabolite 4′-hydroxymethyl-alpha-pyrrolidinohexanophenone in fission yeast heterologously expressing human cytochrome P450 2D6–a versatile alternative to multistep chemical synthesis. J Anal Toxicol 33:190–197CrossRefPubMed

10.

Minakata K, Yamagishi I, Nozawa H, Hasegawa K, Wurita A, Gonmori K, Suzuki M, Watanabe K, Suzuki O (2015) Determination of new pyrrolidino cathinone derivatives, PVT, F-PVP, MPHP, PV8, PV9, and F-PV9, in human blood by MALDI-Q-TOF mass spectrometry. Forensic Toxicol 33:148–154CrossRef

11.

Shintani-Ishida K, Nakamura M, Tojo M, Idota N, Ikegaya H (2015) Identification and quantification of 4-methoxy-α-pyrrolidinobutiophenone (4-MeOPBP) in human plasma and urine using LC–TOF-MS in an autopsy case. Forensic Toxicol 33:348–354CrossRef

12.

Springer D, Fritschi G, Maurer HH (2003) Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4′-methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in rat urine using gas chromatography-mass spectrometry. J Chromatogr B 796:253–266CrossRef

13.

Springer D, Peters FT, Fritschi G, Maurer HH (2002) Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-alpha-pyrrolidinopropiophenone in urine using gas chromatography-mass spectrometry. J Chromatogr B 773:25–33CrossRef

14.

A database for new psychoactive substances, National Institute of Health Sciences, Tokyo, Japan. http://npsdb.nihs.go.jp/Search/ (in Japanese). Accessed December 8, 2015

15.

Wurita A, Hasegawa K, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Suzuki O, Watanabe K (2014) Postmortem distribution of α-pyrrolidinobutiophenone in body fluids and solid tissues of a human cadaver. Leg Med 16:241–246CrossRef

Title: Successful quantification of 4′-methyl-α-pyrrolidinohexanophenone (MPHP) in human urine using LC–TOF-MS in an autopsy case
Authors: Kaori Shintani-Ishida
Yasuhiro Kakiuchi
Hiroshi Ikegaya
Publication date: 01-07-2016
Publisher: Springer Japan
Published in: Forensic Toxicology / Issue 2/2016
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI: https://doi.org/10.1007/s11419-016-0307-z

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Successful quantification of 4′-methyl-α-pyrrolidinohexanophenone (MPHP) in human urine using LC–TOF-MS in an autopsy case

Abstract

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 2/2016

Blood concentrations of α-pyrrolidinovalerophenone (α-PVP) determined in 66 forensic samples

In vitro elucidation of the metabolic profile of the synthetic cannabinoid receptor agonists JWH-175 and JWH-176

Simultaneous determination of cyclic antidepressants and their related drugs and the estimation of new metabolites in human whole blood and urine by MALDI-QTOF-mass spectrometry

Pharmacokinetics of heroin and its metabolites in vitreous humor and blood in a living pig model

Old opioids, new concerns: the case of acetylfentanyl

Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice