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).