6686. Norbolethone

Nomenclature

CAS number: 1235-15-0
(17α)-(±)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-3-one; dl-13β,17α-diethyl-17β-hydroxygon-4-en-3-one; Wy-3475.
C21H32O2; mol wt 316.48.
C 79.70%, H 10.19%, O 10.11%.

Description and references

19-nor anabolic steroid. Prepn of dl-, d-, and l-forms: Smith et al., J. Chem. Soc. 1964, 4472. Biological activities of dl-, d-, and l-forms: Edgren et al., Steroids 2, 731 (1963). Toxicity study: E. I Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). GC/MS determn in athletes' urine: D. H. Catlin et al., Rapid Commun. Mass Spectrom. 16, 1273 (2002).

Chemical structure

Properties

Crystals from alcohol, mp 144-145°. uv max: 241 nm (ε 16500). LD50 orally in mice: >5010 mg/kg (Goldenthal).

Derivative

d-Form.

Nomenclature

CAS number: 28439-19-2

Properties

Crystals from acetone + hexane, mp 175-176°. [α]D +20.7° (in chloroform).

Derivative

l-Form.

Properties

Crystals from acetone + hexane, mp 172-175.5°. [α]D -18.1° (in chloroform).

Note

This is a controlled substance (anabolic steroid): 21 CFR, 1308.13, as defined in 1300.01.