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Rapid Communications in Mass Spectrometry

Rapid Communications in Mass Spectrometry

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Chromatographic-mass spectrometric analysis of the urinary metabolite profile of chlorphenesin observed after dermal application of chlorphenesin-containing sunscreen

Published:25 August 2021 DOI: 10.1002/rcm.9183 PMID: 34431558
Ana Rubio, Christian G?rgens, Oliver Krug, Masato Okano, Matthew Fedoruk, Brian Ahrens, Hans Geyer, Mario Thevis

Abstract

RATIONALE Chlorphenesin is an approved biocide frequently used in cosmetics, and its carbamate ester is an approved skeletal muscle relaxant in certain countries for the treatment of discomfort related to skeletal muscle trauma and inflammation. A major urinary metabolite is 4-chlorophenoxy acetic acid (4-CPA), also known as para-chlorophenoxyacetate (pCPA), which is also employed as target analyte in sports drug testing to detect the use of the prohibited nootropic stimulant meclofenoxate. In order to distinguish between 4-CPA resulting from chlorphenesin, chlorphenesin carbamate, and meclofenoxate, urinary metabolite profiles of chlorphenesin after legitimate use were investigated. METHODS Human administration studies with commercially available sunscreen containing 0.25% by weight of chlorphenesin were conducted. Six study participants dermally applied 8 g of sunscreen and collected urine samples before and up to 7 days post-application. Another set of six study participants applied 8 g of sunscreen on three consecutive days and urine samples were also taken for up to 5 days after the last dosing. Urine specimens were analyzed by liquid chromatography-high resolution (tandem) mass spectrometry, and urinary metabolites were identified in accordance with literature data by accurate mass analysis of respective precursor and characteristic product ions. RESULTS In accordance with literature data, chlorphenesin yielded the characteristic urinary metabolites chlorphenesin glucuronide, chlorphenesin sulfate, and 3-(4-chlorophenoxy)-2-hydroxypropanoic acid (4-CPP) as well as the common metabolite 4-CPA. 4-CPA and 4-CPP were observed at similar abundances, with urinary concentrations of 4-CPA reaching up to approximately 1500 ng/mL and 2300 ng/mL after single and multiple sunscreen application, respectively. CONCLUSION 4-CPA is a common metabolite of meclofenoxate, chlorphenesin and chlorphenesin carbamate. Monitoring the diagnostic urinary metabolites of chlorphenesin provides conclusive supporting evidence whether chlorphenesin or the prohibited nootropic meclofenoxate was administered.

Substances (9)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Chlorphenesin 104-29-0 C9H11ClO3 574 suppliers $8.00-$847.00
4-Chlorophenylacetic acid 1878-66-6 C8H7ClO2 566 suppliers $5.00-$1920.00
4-Chlorophenoxyacetic acid 122-88-3 C8H7ClO3 501 suppliers $10.00-$908.86
2-(4-CHLOROPHENOXY) PROPIONIC ACID 3307-39-9 C9H9ClO3 99 suppliers $10.00-$1114.58
Chlorphenesin carbamate 886-74-8 C10H12ClNO4 56 suppliers $87.00-$4984.40
2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate 51-68-3 C12H16ClNO3 36 suppliers Inquiry
2-(4-chlorophenoxy)-3-methylbutanoic acid 76075-79-1 C11H13ClO3 9 suppliers $22.00-$1491.68
Chlorphenesin Carbamate Isomer 61514-96-3 C10H12ClNO4 6 suppliers Inquiry
chlorphenesin carbamate 126632-50-6 C10H12ClNO4 - Inquiry

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