275. Allopregnan-3α-ol-20-one

Nomenclature

CAS number: 516-54-1
(3α,5α)-3-Hydroxypregnan-20-one; 3α-Hydroxy-5α-dihydroprogesterone; 5α-pregnan-3α-ol-20-one; epiallopregnanolone; allotetrahydroprogesterone.
C21H34O2; mol wt 318.49.
C 79.19%, H 10.76%, O 10.05%.

Description and references

Naturally occurring metabolite of progesterone. Prototype of the neuroactive steroids known as epalons that allosterically modulate γ-aminobutyric acid type A (GABAA) receptors in the CNS. Isoln from human pregnancy urine: R. E. Marker et al., J. Am. Chem. Soc. 59, 616 (1937). Prepn from pregnenolone: G. Fleischer et al., ibid. 60, 79 (1938). Chromatographic determn in urine: F. J. Bègue et al., J. Chromatogr. Sci. 12, 763 (1974). Synthesis, metabolism and pharmacology: R. H. Purdy et al., J. Med. Chem. 33, 1572 (1990). Review of pharmacology and therapeutic potential of epalons: K. W. Gee et al., Crit. Rev. Neurobiol. 9, 207-227 (1995).

Chemical structure

Properties

Crystals from abs alc, mp 176-178°. [α]D +87.7° (abs alc).

Derivative

Acetate.
C23H36O3; mol wt 360.53.
C 76.62%, H 10.06%, O 13.31%.

Properties

Crystals from aq ethanol, mp 141-142°. [α]D22 +94.5° (abs ethanol).