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

Producción científica: Article › revisión exhaustiva

12 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	359-363
Número de páginas	5
Publicación	Chromatographia
Volumen	60
N.º	5-6
DOI	https://doi.org/10.1365/s10337-004-0389-3
Estado	Published - sept 2004

Nota bibliográfica

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.

Financiación

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.

Financiadores
National Horsemen’s

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Clinical Biochemistry
Organic Chemistry

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10.1365/s10337-004-0389-3

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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 - Karpiesiuk, W.

AU - Lehner, A. F.

AU - Hughes, C. G.

AU - Tobin, T.

N1 - 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.

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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.

KW - Anabolic steroid, synthesis

KW - Designer drug

KW - Gas chromatography-mass spectrometry

KW - Tetrahydrogestrinone

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JO - Chromatographia

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

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

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