Pregnan-3alpha-ol-20-one
Title: Pregnan-3a-ol-20-one
CAS Registry Number: 128-20-1
CAS Name: (3a,5b)-3-Hydroxypregnan-20-one
Additional Names: 3a-hydroxy-5b-pregnan-20-one; pregnanolone; eltanolone
Manufacturers' Codes: KABI 2213
Molecular Formula: C21H34O2
Molecular Weight: 318.49
Percent Composition: C 79.19%, H 10.76%, O 10.05%
Literature References: Naturally occurring metabolite of progesterone, q.v. Isoln from urine of pregnant women: R. E. Marker, O. Kamm, J. Am. Chem. Soc. 59, 1373 (1937); from bile of pregnant cows: W. H. Pearlman, E. Cerceo, J. Biol. Chem. 176, 847 (1948). Prepn: R. E. Marker et al., J. Am. Chem. Soc. 59, 1841 (1937); L. Gyermek et al., J. Med. Chem. 11, 117 (1968); T. L. G. Lemos, J. D. McChesney, J. Nat. Prod. 53, 152 (1990). Pharmacokinetics and pharmacodynamics: P. Carl et al., Acta Anaesthesiol. Scand. 38, 734 (1994). Comparative clinical evaluation: J. Van Hemelrijck et al., Anesthesiology 80, 36 (1994); H. Eriksson et al., Acta Anaesthesiol. Scand. 39, 479 (1995). Hemodynamic effects in humans: J. W. Sear et al., J. Clin. Anesth. 7, 126 (1995).
Properties: Needles from aq methanol, mp 148-148.5° (Pearlman, Cerceo); also reported as cryst from hexane, mp 131-132° (Lemos, McChesney). [a]D23 +59.6° (c = 0.3 in chloroform). [a]D26 +108.5 ±1° (c = 9.23 mg/1.23 ml abs ethanol). LD50 in mice, rats (mg/kg): 66 ± 10, 27.5 ± 2.4 i.v. (Gyermek).
Melting point: mp 148-148.5° (Pearlman, Cerceo); mp 131-132° (Lemos, McChesney)
Optical Rotation: [a]D23 +59.6° (c = 0.3 in chloroform); [a]D26 +108.5 ±1° (c = 9.23 mg/1.23 ml abs ethanol)
Toxicity data: LD50 in mice, rats (mg/kg): 66 ± 10, 27.5 ± 2.4 i.v. (Gyermek)
Therap-Cat: Anesthetic (local).

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