Preparation and chromatographic characterization of tetrahydrogestrinone, a new "designer" anabolic steroid

W. Karpiesiuk; A. F. Lehner; C. G. Hughes; T. Tobin

doi:10.1365/s10337-004-0389-3

Preparation and chromatographic characterization of tetrahydrogestrinone, a new "designer" anabolic steroid

W. Karpiesiuk, A. F. Lehner, C. G. Hughes, T. Tobin

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Tetrahydrogestrinone (THG, (17α)-13β-ethyl-17β-hydroxy-18, 19-dinorpregna-4,9,11-trien-3-one, C₂₁H₂₈O₂, 312 m.w.) is a synthetic 19-norsteroid closely related to gestrinone ((17α)-13β-ethyl-17β-hydroxy-18,19-dinorpregna-4,9, 11-trien-20-yn-3-one, C₂₁H₂₄O₂, 308 m.w.) which was originally developed as an oral contraceptive for women. Recent press reports detail the probable use of THG by athletes to enhance athletic performance, and the FDA has banned THG, declaring it a "designer drug." THG has been difficult to analyze because of its instability, lack of commercially available analytical standards, and the fact that no published synthetic methods for the compound exist. We now report a method for the preparation of THG via the carefully controlled hydrogenation of gestrinone.

Original language	English
Pages (from-to)	359-363
Number of pages	5
Journal	Chromatographia
Volume	60
Issue number	5-6
DOIs	https://doi.org/10.1365/s10337-004-0389-3
State	Published - Sep 2004

Bibliographical note

Funding Information:
This research is supported by funding from the Alabama, Arkansas, Kentucky, Pennsylvania, Ohio, Michigan, Charles- ton WV, Florida, Nebraska, and the National Horsemen’s Benevolent and Protective Associations and Mrs. John Hay Whitney.

Keywords

Anabolic steroid, synthesis
Designer drug
Gas chromatography-mass spectrometry
Tetrahydrogestrinone

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry
Clinical Biochemistry

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10.1365/s10337-004-0389-3

Cite this

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title = "Preparation and chromatographic characterization of tetrahydrogestrinone, a new {"}designer{"} anabolic steroid",

abstract = "Tetrahydrogestrinone (THG, (17α)-13β-ethyl-17β-hydroxy-18, 19-dinorpregna-4,9,11-trien-3-one, C21H28O2, 312 m.w.) is a synthetic 19-norsteroid closely related to gestrinone ((17α)-13β-ethyl-17β-hydroxy-18,19-dinorpregna-4,9, 11-trien-20-yn-3-one, C21H24O2, 308 m.w.) which was originally developed as an oral contraceptive for women. Recent press reports detail the probable use of THG by athletes to enhance athletic performance, and the FDA has banned THG, declaring it a {"}designer drug.{"} THG has been difficult to analyze because of its instability, lack of commercially available analytical standards, and the fact that no published synthetic methods for the compound exist. We now report a method for the preparation of THG via the carefully controlled hydrogenation of gestrinone.",

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author = "W. Karpiesiuk and Lehner, {A. F.} and Hughes, {C. G.} and T. Tobin",

note = "Funding Information: This research is supported by funding from the Alabama, Arkansas, Kentucky, Pennsylvania, Ohio, Michigan, Charles- ton WV, Florida, Nebraska, and the National Horsemen{\textquoteright}s Benevolent and Protective Associations and Mrs. John Hay Whitney.",

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AU - Tobin, T.

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N2 - Tetrahydrogestrinone (THG, (17α)-13β-ethyl-17β-hydroxy-18, 19-dinorpregna-4,9,11-trien-3-one, C21H28O2, 312 m.w.) is a synthetic 19-norsteroid closely related to gestrinone ((17α)-13β-ethyl-17β-hydroxy-18,19-dinorpregna-4,9, 11-trien-20-yn-3-one, C21H24O2, 308 m.w.) which was originally developed as an oral contraceptive for women. Recent press reports detail the probable use of THG by athletes to enhance athletic performance, and the FDA has banned THG, declaring it a "designer drug." THG has been difficult to analyze because of its instability, lack of commercially available analytical standards, and the fact that no published synthetic methods for the compound exist. We now report a method for the preparation of THG via the carefully controlled hydrogenation of gestrinone.

AB - Tetrahydrogestrinone (THG, (17α)-13β-ethyl-17β-hydroxy-18, 19-dinorpregna-4,9,11-trien-3-one, C21H28O2, 312 m.w.) is a synthetic 19-norsteroid closely related to gestrinone ((17α)-13β-ethyl-17β-hydroxy-18,19-dinorpregna-4,9, 11-trien-20-yn-3-one, C21H24O2, 308 m.w.) which was originally developed as an oral contraceptive for women. Recent press reports detail the probable use of THG by athletes to enhance athletic performance, and the FDA has banned THG, declaring it a "designer drug." THG has been difficult to analyze because of its instability, lack of commercially available analytical standards, and the fact that no published synthetic methods for the compound exist. We now report a method for the preparation of THG via the carefully controlled hydrogenation of gestrinone.

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Preparation and chromatographic characterization of tetrahydrogestrinone, a new "designer" anabolic steroid

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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