Next Article in Journal
Elicitation: A Tool for Enriching the Bioactive Composition of Foods
Previous Article in Journal
Novel Schiff Bases Based on the Quinolinone Skeleton: Syntheses, X-ray Structures and Fluorescent Properties
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(9), 13526-13540; doi:10.3390/molecules190913526

Synthesis of [13C4]-labeled ∆9-Tetrahydrocannabinol and 11-nor-9-Carboxy-∆9-tetrahydrocannabinol as Internal Standards for Reducing Ion Suppressing/Alteration Effects in LC/MS-MS Quantification

1
Department of Chemistry, Norwegian University of Science and Technology, Høgskoleringen 5, 7491 Trondheim, Norway
2
Chiron AS, Stiklestadveien 1, 7041 Trondheim 7041, Norway
*
Author to whom correspondence should be addressed.
Received: 30 July 2014 / Revised: 22 August 2014 / Accepted: 26 August 2014 / Published: 1 September 2014
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1064 KB, uploaded 1 September 2014]   |  

Abstract

(−)-∆9-Tetrahydrocannabinol is the principal psychoactive component of the cannabis plant and also the active ingredient in some prescribed drugs. To detect and control misuse and monitor administration in clinical settings, reference samples of the native drugs and their metabolites are needed. The accuracy of liquid chromatography/mass spectrometric quantification of drugs in biological samples depends among others on ion suppressing/alteration effects. Especially, 13C-labeled drug analogues are useful for minimzing such interferences. Thus, to provide internal standards for more accurate quantification and for identification purpose, synthesis of [13C4]-∆9-tetrahydro-cannabinol and [13C4]-11-nor-9-carboxy-∆9-tetrahydrocannabinol was developed via [13C4]-olivetol. Starting from [13C4]-olivetol the synthesis of [13C4]-11-nor-9-carboxy-∆9-tetrahydrocannabinol was shortened from three to two steps by employing nitromethane as a co-solvent in condensation with (+)-apoverbenone. View Full-Text
Keywords: 13C-labeled standards; [13C4]-olivetol; [13C4]-∆9-tetrahydrocannabinol; [13C4]-11-nor-9-carboxy-∆9-tetrahydrocannabinol 13C-labeled standards; [13C4]-olivetol; [13C4]-∆9-tetrahydrocannabinol; [13C4]-11-nor-9-carboxy-∆9-tetrahydrocannabinol
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Karlsen, M.; Liu, H.; Johansen, J.E.; Hoff, B.H. Synthesis of [13C4]-labeled ∆9-Tetrahydrocannabinol and 11-nor-9-Carboxy-∆9-tetrahydrocannabinol as Internal Standards for Reducing Ion Suppressing/Alteration Effects in LC/MS-MS Quantification. Molecules 2014, 19, 13526-13540.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top