1,4,6-Androstatriene-3,17-dione

Chemical compound changed 413468625 (8R,9S,10R,13S,14S)-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthrene-3,17-dione 1,4,6-androstatrien-3,17-dione.png skin-invert-image X Supplement Oral Hepatic 48 hours 633-35-2 correct FDA 217A6T1V8N 104880 correct drugbank correct chemspider 94659 correct EBI 131190 19 22 2 O=C\4\C=C/[C@]3(C(/C=C\[C@H]2[C@H]1[C@@](C(=O)CC1)(CC[C@@H]23)C)=C/4)C correct chemspider 1S/C19H22O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3-4,7,9,11,14-16H,5-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1 correct chemspider DKVSUQWCZQBWCP-QAGGRKNESA-N 1,4,6-Androstatriene-3,17-dione (ATD) is a potent irreversible aromatase inhibitor that inhibits estrogen biosynthesis by permanently binding and inactivating aromatase in adipose and peripheral tissue. Covey DF, Hood WF Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatriene-3,17-dione cause a time-dependent decrease in human placental aromatase activity Endocrinology 108 4 1597–1599 April 1981 7472286 10.1210/endo-108-4-1597 It is used to control estrogen synthesis. Adkins-Regan E, Leung CH Sex steroids modulate changes in social and sexual preference during juvenile development in zebra finches Hormones and Behavior 50 5 772–778 December 2006 16919276 10.1016/j.yhbeh.2006.07.003 Elsevier Inc 23869106 ATD was present in some over-the-counter bodybuilding supplements until 2009, as well as Topical ATD solutions that work transdermally. The product was developed and commercialized in the dietary supplement market place by industry journeyman Bruce Kneller, who holds a United States Patent for use of the compound and related compounds (#7,939,517) and Gaspari Nutrition. ATD has many names in sports supplements including: 1,4,6 etiollochan-dione, 3, 17-keto-etiochol-triene, androst-1,4,6-triene-3,17-dione and many others. These all refer to CAS# 633-35-2. ATD may cause a positive test for the anabolic steroid Boldenone, of which it is a possible metabolite and production contaminant. ATD is also prohibited in amateur and professional sports which forbids aromatase inhibitors. Parr MK, Fusshöller G, Schlörer N, Opfermann G, Piper T, Rodchenkov G, Schänzer W Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control Rapid Communications in Mass Spectrometry 23 2 207–218 January 2009 19089863 10.1002/rcm.3861 2009RCMS...23..207P A related agent is exemestane (Aromasin). Synthesis The synthesis of 1,4,6-Androstatriene-3,17-dione has been described:Ma, E., Kim, E. (25 May 2005). "Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol". Molecules. 10 (3): 572–582. doi:10.3390/10030572.Kim, E., Ma, E. (April 2007). "Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents". Steroids. 72 (4): 360–367. doi:10.1016/j.steroids.2006.12.008.Turner, A. B. (1966). "Applications of high-potential quinones. Convenient syntheses of steroidal 1,4,6-trien-3-ones". Chemical Communications (London) (23): 845. doi:10.1039/c19660000845.Burg Willem Jacob Van Der, US2879279 (1959 to Organon NV, Organon Inc).Kaufmann, St., Pataki, J., Rosenkranz, G., Romo, J., Djerassi, C. (October 1950). "Steroids. VI. 1 The Wohl—Ziegler Bromination of Steroidal 1,4-Dien-3-ones. Partial Synthesis of ▵ 6 -Dehydroestrone and Equilenin". Journal of the American Chemical Society. 72 (10): 4531–4534. doi:10.1021/ja01166a054. It is most congenially prepared from DHEA by oxidation with DDQ in a single step. Applications It is possible to use 1,4,6-Androstatriene-3,17-dione in the synthesis of estrone.Rubin Martin, Emanuel B Hershberg & Schwenk Erwin, US2594349 (1952 to Merck Sharp and Dohme LLC). However, the modern process seems to rely on Boldione.田伟生, 史勇 & 汪昀, CN107602650 (2018 to Shanghai Institute of Organic Chemistry of CAS). 1,4,6-Androstatriene-3,17-dione is used in the synthesis of 1-Methylestrone methyl ether, PC22295924.S Laing & P Sykes, 3717627 (1973 to Glaxo Laboratories Ltd). Birch reduction of this and work-up can lead to some interesting steroids with a 1-methyl group,Howard J Ringold & Rosenkranz George, 3032552 (1962 to Syntex SA). although according to Dan the methyl group is in the beta-configuration.Lednicer, D. 2011 Steroid chemistry at a glance Wiley Chemistry at a glance 1. publ 978-0-470-66084-3 However, according to one patent, there is a scrambling of alpha/beta epimers and not a single isomer.David Darwin Evans, GB1003301 (1965 to Parke Davis and Co LLC). Hence, this is the estrane equivalent of Demalon [2881-21-2] but a mixture of epimers. References Further reading Ellinwood WE, Hess DL, Roselli CE, Spies HG, Resko JA Inhibition of aromatization stimulates luteinizing hormone and testosterone secretion in adult male rhesus monkeys The Journal of Clinical Endocrinology and Metabolism 59 6 1088–1096 December 1984 6541658 10.1210/jcem-59-6-1088 Category:Androstanes Category:Aromatase inhibitors Category:Bodybuilding supplements Category:Diketones