A positive allosteric modulator of the GABAA receptor
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5α-Pregnane-3α,20β-diol

Item No. 45534

Product Insert (PDF)
Technical Information
Formal Name
(3α,5α,20R)-pregnane-3,20-diol
CAS Number
566-57-4
Synonyms
  • 3α,20β-Dihydroxy-5α-pregnane
Molecular Formula
C21H36O2
Formula Weight
320.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/mlEthanol: Soluble: ≥10 mg/ml
SMILES
C[C@@]12[C@]3([H])[C@](CC[C@@]1([H])C[C@@H](CC2)O)([H])[C@@]4([H])[C@](CC3)([C@]([C@H](O)C)([H])CC4)C
InChi Code
InChI=1S/C21H36O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15-,16+,17-,18+,19+,20+,21-/m1/s1
InChi Key
YWYQTGBBEZQBGO-HZCKZVNYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

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    Product Description

    5α-Pregnane-3α,20β-diol is a positive allosteric modulator (PAM) of the GABAA receptor (GABAAR) and an active metabolite of progesterone (Item No. 15876).1,2 It is enzymatically formed from progesterone via 5α-pregnane-3,20-dione and 3β-hydroxy-5α-pregnan-20-one intermediates.1 5α-Pregnane-3α,20β-diol increases the binding of the GABAAR agonist muscimol (Item No. 13667) to the high and low affinity sites of the GABAAR in rat cortical membrane suspensions (EC50s = 33 and 1.7 nM, respectively).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stanczyk, F.Z., McGough, A., Chagam, L., et al. Metabolism of progestogens used for contraception and menopausal hormone therapy. Steroids 207, 109427 (2024).

    2. Goodnough, D.B., and Hawkinson, J.E. Neuroactive steroid modulation of [3H]muscimol binding to the GABAA receptor complex in rat cortex. Eur. J. Pharmacol. 288(2), 157-162 (1995).