:Bolmantalate

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = [(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] adamantane-1-carboxylate

| image = Bolmantalate.svg

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| routes_of_administration = Intramuscular injection

| class = Androgen; Anabolic steroid; Androgen ester; Progestogen

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1491-81-2

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| PubChem = 11954312

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| ChemSpiderID = 10128607

| UNII = 7IKT9C4TYI

| ChEMBL = 2104237

| KEGG = D03147

| synonyms = LY-38851; Lilly 38851; Nandrolone adamantoate; Nandrolone adamantane-1-carboxylate; 19-Nortestosterone 17β-adamantoate

| C=29 | H=40 | O=3

| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)C45CC6CC(C4)CC(C6)C5)CCC7=CC(=O)CC[C@H]37

| StdInChI_Ref =

| StdInChI = 1S/C29H40O3/c1-28-9-8-23-22-5-3-21(30)13-20(22)2-4-24(23)25(28)6-7-26(28)32-27(31)29-14-17-10-18(15-29)12-19(11-17)16-29/h13,17-19,22-26H,2-12,14-16H2,1H3/t17?,18?,19?,22-,23+,24+,25-,26-,28-,29?/m0/s1

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| StdInChIKey = NCXAMLZZPQRJGY-PVAKYVEVSA-N

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Bolmantalate (developmental code name LY-38851 or Lilly 38851), also known as 19-nortestosterone 17β-adamantoate (or nandrolone adamantoate), is an androgen and anabolic steroid and a nandrolone ester which was synthesized and developed by Eli Lilly in 1965 but was never marketed.{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA168|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=168–}}{{cite journal | vauthors = Rapala RT, Kraay RJ, Gerzon K | title = The adamantyl group in medicinal agents. II. Anabolic steroid 17-beta-adamantoates | journal = J. Med. Chem. | volume = 8 | issue = 5 | pages = 580–3 | date = September 1965 | pmid = 5867938 | doi = 10.1021/jm00329a007 }}

{{Relative affinities of nandrolone and related steroids}}