638. Androstenedione

Nomenclature

CAS number: 63-05-8
Androst-4-ene-3,17-dione; Δ4-androstenedione; Δ4-etiocholendione-3,17.
C19H26O2; mol wt 286.41.
C 79.68%, H 9.15%, O 11.17%.

Description and references

Weak androgen produced by the adrenal gland; converted in peripheral tissues to testosterone or estrone, q.q.v. Prepn: L. Ruzicka, A. Wettstein, Helv. Chim. Acta 18, 986 (1935); E. S. Wallis, E. Fernholz, J. Am. Chem. Soc. 57, 1511 (1935); and physiological activity: A. Butenandt, H. Kudszus, Z. Physiol. Chem. 237, 75 (1935). Isoln from adrenal cortex: J. von Euw, T. Reichstein, Helv. Chim. Acta 24, 879 (1941). Physiology: V. H. T. James, A. B. Goodall in Proc. 9th Congr. Hung. Soc. Endocrinol. Metab., F. A. Laszlo, Ed. (Akad. Kiado, Budapest, 1979) pp 235-241. HPLC determn in plasma or serum: V. R. Walker et al., Anal. Biochem. 234, 194 (1996). Discussion of use as dietary supplement: L. Schnirring, Physician Sportsmed. 26, 15-18 (1998). Clinical effect of oral supplement on blood chemistry: D. S. King et al., J. Am. Med. Assoc. 281, 2020 (1999).

Chemical structure

Properties

Crystals from hexane, mp 173-174°. [α]D30 +199° (in chloroform).

Note

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