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Synthesis and bioanalytical evaluation of morphine-3-O-sulfate and morphine-6-O-sulfate in human urine and plasma using LC-MS/MS
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.ORCID iD: 0000-0002-8444-181X
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2012 (English)In: Journal of Separation Science, ISSN 1615-9306, E-ISSN 1615-9314, Vol. 35, no 3, 367-375 p.Article in journal (Refereed) Published
Abstract [en]

The aim of this work was to synthesize morphine-3-O-sulfate and morphine-6-O-sulfate for use as reference substances, and to determine the sulfate conjugates as possible heroin and morphine metabolites in plasma and urine by a validated LC-MS/MS method. Morphine-6-O-sulfate and morphine-3-O-sulfate were prepared as dihydrates from morphine hydrochloride, in overall yields of 41 and 39% with product purities of >99.5% and >98%, respectively. For bioanalysis, the chromatographic system consisted of a reversed-phase column and gradient elution. The tandem mass spectrometer was operated in the positive electrospray mode using selected reaction monitoring, of transition m/z 366.15 to 286.40. The measuring range was 5500?ng/mL for morphine-3-O-sulfate and 4.5454?ng/mL for morphine-6-O-sulfate in plasma. In urine, the measuring range was 505000?ng/mL for morphine-3-O-sulfate and 45.44544?ng/mL for morphine-6-O-sulfate. The intra-assay and total imprecision (coefficient of variation) was below 11% for both analytes in urine and plasma. Quantifiable levels of morphine-3-O-sulfate in authentic urine and plasma samples were found. Only one authentic urine sample contained a detectable level of morphine-6-O-sulfate, while no detectable morphine-6-O-sulfate was found in plasma samples.

Place, publisher, year, edition, pages
2012. Vol. 35, no 3, 367-375 p.
Keyword [en]
Human, LC-MS, MS, Morphine-3-O-sulfate, Morphine-6-O-sulfate, Synthesis
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-91129DOI: 10.1002/jssc.201100739ISI: 000299254000004ScopusID: 2-s2.0-84856094352OAI: diva2:508724
QC 20120309Available from: 2012-03-09 Created: 2012-03-08 Last updated: 2012-03-09Bibliographically approved

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