6365. Nandrolone
Nomenclature
CAS number: 434-22-0
(17β)-17-Hydroxyestr-4-en-3-one; 17β-hydroxy-4-estren-3-one; 4-estren-17β-ol-3-one; 17β-hydroxy-19-nor-4-androsten-3-one; 19-nortestosterone. C18H26O2; mol wt 274.40.
C 78.79%, H 9.55%, O 11.66%.
Description and references
Prepd from alkyl ethers of estradiol: Birch, Q. Rev. Chem. Soc. 4, 69 (1950); Wilds, Nelson, J. Am. Chem. Soc. 75, 5366 (1953). Alternate syntheses: H. Ueberwasser et al., Helv. Chim. Acta 46, 344 (1963); I. Shimizu et al., Tetrahedron Lett. 21, 487 (1980).
Properties
Dimorphic crystals, mp 112° and 124°. [α]D22 +55° (c = 0.93 in chloroform). uv max (ethanol): 241 nm (ε 17000). Sol in alcohol, ether, chloroform.Derivative
Benzoate.C25H30O3; mol wt 378.50.
C 79.33%, H 7.99%, O 12.68%.
Properties
Needles from 75% alc, mp 174-175°. [α]D20 +104.5° (alc).Derivative
Cyclohexanecarboxylate.Nomenclature
CAS number: 18470-94-5
19-Nortestosterone hexahydrobenzoate. C25H36O3; mol wt 384.55.
C 78.08%, H 9.44%, O 12.48%.
Properties
Small, elongated prisms from petr ether, mp 88-89°, [α]D20 +50° (c = 0.5 in chloroform).Derivative
Decanoate.Nomenclature
CAS number: 360-70-3
19-Nortestosterone decanoate; Deca-Durabolin (Organon); Retabolil; Retabolil (Richter Gedeon). C28H44O3; mol wt 428.65.
C 78.46%, H 10.35%, O 11.20%.
Properties
White to yellow crystals, mp 32-35°. Practically insol in water. Freely sol in ethanol, ether, acetone, chloroform, oils.Derivative
Dodecanoate.Nomenclature
CAS number: 26490-31-3
Nandrolone laurate; Laurabolin (Intervet). C30H48O3; mol wt 456.70.
C 78.90%, H 10.59%, O 10.51%.
Derivative
p-Hexyloxyphenylpropionate.Nomenclature
CAS number: 52279-57-9
19-Nortestosterone-3-(p-hexyloxyphenyl)propionate. C33H46O4; mol wt 506.72.
C 78.22%, H 9.15%, O 12.63%.
Properties
Crystals, mp 53-55°. [α]D +45° (c = 1.0 in dioxane).Derivative
Phenpropionate.Nomenclature
CAS number: 62-90-8
19-Nortestosterone β-phenylpropionate; Durabolin (Organon); Superanabolon (Spofa); Nandrolin (Intervet). C27H34O3; mol wt 406.56.
C 79.76%, H 8.43%, O 11.81%.
Properties
Crystals, mp 95-96°. [α]D +58° (chloroform).Derivative
Propionate.Nomenclature
CAS number: 7207-92-3
19-Nortestosterone propionate. C21H30O3; mol wt 330.46.
C 76.33%, H 9.15%, O 14.52%.
Properties
Crystals from aqueous methanol or isopropyl ether, mp 55-60°. [α]D23.5 +58° in chloroform (Rao). uv max: 240 nm (ε 16650).Note
This is a controlled substance (anabolic steroid): 21 CFR, 1308.13, as defined in 1300.01.Therapeutic Category
Anabolic.
Therapeutic Category (Veterinary)
Phenpropionate as anabolic steroid.Keywords
Anabolic