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Komarapuri S, Krishnan K, Covey DF. Synthesis of 19-Trideuterated ent-Testosterone and the GABA(A) Receptor Potentiators ent-Androsterone and ent-Etiocholanolone. J Labelled Comp Radiopharm. 2008;51(14):430-434doi: 10.1002/jlcr.1558.
Komarapuri, S., Krishnan, K., & Covey, D. F. (2008). Synthesis of 19-Trideuterated ent-Testosterone and the GABA(A) Receptor Potentiators ent-Androsterone and ent-Etiocholanolone. Journal of labelled compounds & radiopharmaceuticals, 51(14), 430-434. https://doi.org/10.1002/jlcr.1558
Komarapuri, Shirisha, et al. "Synthesis of 19-Trideuterated ent-Testosterone and the GABA(A) Receptor Potentiators ent-Androsterone and ent-Etiocholanolone." Journal of labelled compounds & radiopharmaceuticals vol. 51,14 (2008): 430-434. doi: https://doi.org/10.1002/jlcr.1558
Komarapuri S, Krishnan K, Covey DF. Synthesis of 19-Trideuterated ent-Testosterone and the GABA(A) Receptor Potentiators ent-Androsterone and ent-Etiocholanolone. J Labelled Comp Radiopharm. 2008 Nov;51(14):430-434. doi: 10.1002/jlcr.1558. PMID: 19122784; PMCID: PMC2613317.
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J Labelled Comp Radiopharm. 2008 Nov;51(14):430-434. doi: 10.1002/jlcr.1558.

Synthesis of 19-Trideuterated ent-Testosterone and the GABA(A) Receptor Potentiators ent-Androsterone and ent-Etiocholanolone.

Journal of labelled compounds & radiopharmaceuticals

Shirisha Komarapuri, Kathiresan Krishnan, Douglas F Covey

Affiliations

  1. Washignton Univ. school of Medicine, Developmental Biology.

PMID: 19122784 PMCID: PMC2613317 DOI: 10.1002/jlcr.1558

Abstract

19-Trideuteromethyl enantiomers of androgens namely ent-testosterone, ent-androsterone and ent-etiocholanolone were prepared by total synthesis. The isotope labeling at the carbon-19 angular methyl group was achieved by using deuterated methyl iodide (99.5% d(3)) for introduction of C-19 before closure of the steroid A-ring. This method yields 19,19,19-trideuterated steroids without increasing the number of steps involved in the total synthesis of ent-androgens. Analysis by mass spectrometry showed no loss of deuterium during incorporation of C-19 into ent-testosterone. The availability of the compounds will enable these ent-androgens to be distinguished by mass spectrometry from their natural enantiomers in future pharmacokinetic and metabolic studies.

References

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