MilliporeSigma
  • Home
  • Search Results
  • GC-MS, LC-MS(n), LC-high resolution-MS(n), and NMR studies on the metabolism and toxicological detection of mesembrine and mesembrenone, the main alkaloids of the legal high "Kanna" isolated from Sceletium tortuosum.

GC-MS, LC-MS(n), LC-high resolution-MS(n), and NMR studies on the metabolism and toxicological detection of mesembrine and mesembrenone, the main alkaloids of the legal high "Kanna" isolated from Sceletium tortuosum.

Analytical and bioanalytical chemistry (2014-09-23)
Golo M J Meyer, Carina S D Wink, Josef Zapp, Hans H Maurer
ABSTRACT

Mesembrine and mesembrenone are the main alkaloids of Sceletium tortuosum, a plant species that was used for sedation and analgesia by the KhoiSan, previously known as Hottentots, a tribe in South Africa. After fermentation, the obtained preparation called "Kanna" or "Kougoed" was used by chewing, smoking, or sniffing. Today, Kanna gains popularity by drug users as legal high. For monitoring such consumption, metabolism studies are mandatory because the metabolites are mostly the analytical targets, especially in urine. Therefore, the metabolism of both alkaloids was investigated in rat urine and pooled human liver preparations after several sample work-up procedures. As both alkaloids were not commercially available, they were isolated from plant material by Soxhlet extraction, and their identity confirmed by NMR. The metabolites were identified using gas chromatography-mass spectrometry (GC-MS) and liquid chromatography coupled to linear ion trap high resolution mass spectrometry (LC-HR-MS(n)). Both alkaloids were O- and N-demethylated, dihydrated, and/or hydroxylated at different positions. The phenolic metabolites were partly excreted as glucuronides and/or sulfates. Most of the phase I metabolites identified in rat urine could be detected also in the human liver preparations. After a common user's low dose application of mesembrine, mainly the O- and N demethyl-dihydro, hydroxy, and bis-demethyl-dihydro metabolites, and in case of mesembrenone only the N-demethyl and the N-demethyl-dihydro metabolite could be detected in rat urine using the authors' standard urine screening approaches (SUSA) by GC-MS or LC-MS(n). Thus, it should be possible to monitor a consumption of mesembrine and/or mesembrenone assuming similar pharmacokinetics in humans.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Acetonitrile solution, contains 10.0% acetone, 40.0% 2-propanol, 0.05% formic acid
Sigma-Aldrich
Hydrogen chloride solution, 3 M in cyclopentyl methyl ether (CPME)
Sigma-Aldrich
Methanol, NMR reference standard
Supelco
Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Chloroform, anhydrous, ≥99%, contains 0.5-1.0% ethanol as stabilizer
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.1 % (v/v) TMS
Supelco
Chloroform, suitable for HPLC, ≥99.8%
Sigma-Aldrich
Chloroform-d, 99.8 atom % D
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, anhydrous
Supelco
Ethanol solution, certified reference material, 2000 μg/mL in methanol
Sigma-Aldrich
Acetonitrile solution, contains 0.05 % (v/v) trifluoroacetic acid
Supelco
Chloroform, analytical standard
Sigma-Aldrich
Acetonitrile solution, contains 0.1 % (v/v) trifluoroacetic acid, suitable for HPLC
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D
Sigma-Aldrich
Acetonitrile solution, contains 0.05 % (w/v) ammonium formate, 0.1 % (v/v) formic acid, 5 % (v/v) water, suitable for HPLC
Supelco
Calcium formate, Standard for quantitative NMR, TraceCERT®
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.05 % (v/v) TMS
Sigma-Aldrich
Acetonitrile solution, contains 0.1 % (v/v) formic acid, suitable for HPLC
Sigma-Aldrich
Hydrochloric acid solution, 32 wt. % in H2O, FCC
Sigma-Aldrich
Methanol, HPLC Plus, ≥99.9%, poly-coated bottles
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.5 wt. % silver wire as stabilizer
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Aluminum oxide, mesoporous, MSU-X (wormhole), average pore size 3.8 nm
Sigma-Aldrich
Chloroform, ACS reagent, ≥99.8%, contains 0.5-1.0% ethanol as stabilizer
Sigma-Aldrich
Chloroform, anhydrous, contains amylenes as stabilizer, ≥99%
Sigma-Aldrich
Methanol, anhydrous, 99.8%
Sigma-Aldrich
Chloroform-d, 99.8 atom % D
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform, ACS reagent, ≥99.8%, contains amylenes as stabilizer