19-Nordehydroepiandrosterone

Chemical compound (3S,8R,9S,10R,13S,14S)-3-hydroxy-13-methyl-2,3,4,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one 19-Nordehydroepiandrosterone.svg skin-invert-image 235px By mouth Androgen; anabolic steroid; progestogen correct CAS 17916-75-5 correct FDA 7FA3BH94UY 53990402 277545 19-Nor-DHEA 19-Nor-5-dehydroepiandrosterone 19-Nor-5-DHEA Estr-5-en-3β-ol-17-one 19-Norandrost-5-en-3β-ol-17-one 3β-Hydroxyestr-5-en-17-one 18 25 2 C[C@]12CC[C@@H]3[C@H]4CC[C@@H](CC4=CC[C@H]3[C@@H]1CCC2=O)O 1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,12-16,19H,3-10H2,1H3/t12-,13-,14+,15+,16-,18-/m0/s1 KELRVUIFMYCLHB-MTLKIPAASA-N 19-Nordehydroepiandrosterone (19-nor-DHEA), or 19-nor-5-dehydroepiandrosterone (19-nor-5-DHEA), is an estrane (19-norandrostane) steroid which was never marketed. Poortman J, Vroegindewey-Jie D, Thijssen JH, Schwarz F Relative binding affinity of androstane and C-19-nor-androstane-steroids for the estradiol-receptor in human myometrial and mammary cancer tissue Molecular and Cellular Endocrinology 8 1 27–34 July 1977 881104 10.1016/0303-7207(77)90015-6 24190327 It is the combined derivative of the androgen/anabolic steroid nandrolone (19-nortestosterone) and the androgen prohormone dehydroepiandrosterone (DHEA, or more specifically 5-DHEA). Related compounds include 19-nor-5-androstenediol, bolandiol (19-nor-4-androstenediol), and bolandione (nor-4-androstenedione), which are all known orally active prohormones of nandrolone. Uralets VP, Gillette PA Over-the-counter Δ5 anabolic steroids 5-androsen-3,17-dione; 5-androsten-3β, 17β-diol; dehydroepiandrosterone; and 19-nor-5-androsten-3,17-dione: excretion studies in men Journal of Analytical Toxicology 24 3 188–193 April 2000 10774538 10.1093/jat/24.3.188 free Thieme D, Hemmersbach P Doping in Sports https://books.google.com/books?id=R-hIC-caIn8C&pg=PA137 18 December 2009 Springer Science & Business Media 978-3-540-79088-4 137– Villain M, Cirimele V, Kintz P Substance Abuse in Sports: Detection of Doping Agents in Hair by Mass Spectrometry Yinon J Advances in Forensic Applications of Mass Spectrometry https://books.google.com/books?id=T0vGENZVDaoC&pg=PA138 29 December 2003 CRC Press 978-0-203-99828-1 138– 19-Nor-DHEA may occur as a metabolite of bolandione and related steroids. Synthesis The chemical synthesis of 19-Nordehydroepiandrosterone was reported.Tang Sihua, et al. CN117820407 (2024 to Hubei Tongtong Steroidal Drug Research Institute Co ltd). center|500px The enone group in Bolandione (1) is protected with isopropenyl acetate to give the corresponding enol acetate (3-Hydroxy-17-oxoestra-3,5-dien-3-yl acetate) PC11278466 (2). Ketalization of the remaining carbonyl with ethyleneglycol in the presence of triethyl orthoformate gives (3). Reduction of the enol ether by treatment with sodium borohydride occurred to give PC118447212 (4). Hydrolytic removal of the cyclic ketal in weak acid completed the synthesis of 19-Nor-DHEA (5). See also List of androgens/anabolic steroids References Category:Abandoned drugs Category:Secondary alcohols Category:Androgens Category:Designer prodrugs Category:Estranes Category:Estrogens Category:Sex hormone esters and conjugates Category:Progestogens