Androsta-3,5-diene-7,17-dione

• CAT Number: M047142
• CAS Number: 1420-49-1
• Molecular Formula: C19H24O2
• Molecular Weight: 284.399
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (8R,9S,10R,13S,14S)-10,13-dimethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-7,17-dione
• InChI: InChI=1S/C19H24O2/c1-18-9-4-3-5-12(18)11-15(20)17-13-6-7-16(21)19(13,2)10-8-14(17)18/h3,5,11,13-14,17H,4,6-10H2,1-2H3/t13-,14-,17-,18-,19-/m0/s1
• InChIKey: VHDOTNMSJDQVEE-ZENYQMPMSA-N
• SMILES: CC12CCC3C(C1CCC2=O)C(=O)C=C4C3(CCC=C4)C

Reference

[1]. Drug Test Anal. 2019 Jul;11(7):1109-1115. doi: 10.1002/dta.2589. Epub 2019 May 3.
Identification of the designer steroid Androsta-3,5-diene-7,17-dione in a dietary supplement.
Lorenz LM(1), Toomey VM(1), Lanzarotta AC(1), Flurer RA(1), Falconer TM(1).
Author information: (1)U.S. Food and Drug Administration, Forensic Chemistry Center, Cincinnati, OH, United States.
A liquid chromatography-mass spectrometry (LC-MS) screen for known anabolic-androgenic steroids in a dietary supplement product marketed for "performance enhancement" detected an unknown compound having steroid-like spectral characteristics. The compound was isolated using high performance liquid chromatography with ultraviolet detection (HPLC-UV) coupled with an analytical scale fraction collector. After the compound was isolated, it was then characterized using gas chromatography with simultaneous Fourier Transform infrared detection and mass spectrometry (GC-FT-IR-MS), liquid chromatography-high resolution accurate mass-mass spectrometry (LC-HRAM-MS) and nuclear magnetic resonance (NMR). The steroid had an accurate mass of m/z 285.1847 (error-0.57 ppm) for the protonated species [M + H]+ , corresponding to a molecular formula of C19 H24 O2 . Based on the GC-FT-IR-MS data, NMR data, and accurate mass, the compound was identified as androsta-3,5-diene-7,17-dione. Although this is not the first reported identification of this designer steroid in a dietary supplement, the data provided adds information for identification of this compound not previously reported. This compound was subsequently detected in another dietary supplement product, which contained three additional active ingredients.
Published 2019. This article is a U.S. Government work and is in the public domain in the USA.
DOI: 10.1002/dta.2589 PMID: 30892803 [Indexed for MEDLINE]

[2]. Endocrinol Exp. 1971 Dec;5(4):205-10.
Androsta-3,5-diene-7,17-dione: isolation from urine and formation from 7-keto-dehydro-epiandrosterone sulphate under various conditions of hydrolysis.
Schubert K, Wehrberger K, Hobe G.
PMID: 4274027 [Indexed for MEDLINE]