6967. Oxymetholone

Nomenclature

CAS number: 434-07-1
(5α,17β)-17-Hydroxy-2-(hydroxymethylene)-17-methylandrostan-3-one; 2-hydroxymethylene-17α-methyldihydrotestosterone; 4,5α-dihydro-2-hydroxymethylene-17α-methyltestosterone; 2-hydroxymethylene-17α-methyl-17β-hydroxy-5α-androstan-3-one; 2-hydroxymethylene-17α-methylandrostan-17β-ol-3-one; anasterone; Adroyd (Parke-Davis); Anapolon (Syntex); Anadrol (Syntex); Pardroyd (Parke-Davis); Plenastril (Protochemie); Protanabol; Nastenon; Synasteron.
C21H32O3; mol wt 332.48.
C 75.86%, H 9.70%, O 14.44%.

Description and references

Anabolic steroid. Prepn: Ringold et al., J. Am. Chem. Soc. 81, 427 (1959); Ringold, Rosenkranz, DE 1070632 (1959 to Syntex).

Chemical structure

Properties

Crystals from ethyl acetate, mp 178-180°. [α]D +38°. uv max: 285 nm (log ε 3.99).

Derivative

Enol acetate.
C23H34O4; mol wt 374.51.
C 73.76%, H 9.15%, O 17.09%.

Properties

Crystals from hexane, mp 144-148°. [α]D +27° (ethanol). uv max: 255 nm (log ε 4.09).

Derivative

Enol propionate.
C24H36O4; mol wt 388.54.
C 74.19%, H 9.34%, O 16.47%.

Properties

Crystals from hexane, mp 135°. [α]D +26° (ethanol). uv max: 257 nm (log ε 4.11).

Derivative

Enol benzoate.
C28H36O4; mol wt 436.58.
C 77.03%, H 8.31%, O 14.66%.

Properties

Crystals from acetone + water, mp 188-190°. uv max: 230 nm (log ε 4.19).

Caution

Oxymetholone is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-211. This is a controlled substance (anabolic steroid): 21 CFR, 1308.13, as defined in 1300.01.

Therapeutic Category

Androgen.

Therapeutic Category (Veterinary)

Anabolic steroid for small animals.

Keywords

Androgen