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IUPAC name
3β-Hydoxy-5β-pregnan-20-one
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Other names
3β,5β-tetrahydroprogesterone
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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Properties | |
C21H34O2 | |
Molar mass | 318.49 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
Epipregnanolone, also known as 3β-hydoxy-5β-pregnan-20-one or 3β,5β-tetrahydroprogesterone (3β,5β-THP), is an endogenous neurosteroid. It acts as a negative allosteric modulator of the GABAA receptor and reverses the effects of potentiators like allopregnanolone. Epipregnanolone is biosynthesized from progesterone by the actions of 5β-reductase and 3β-hydroxysteroid dehydrogenase, with 5β-dihydroprogesterone as the intermediate in this two-step transformation.
Epipregnanolone is not a progestogen itself, but via metabolization into other steroids, behaves indirectly as one.
The sulfate of epipreganolone, epipregnanolone sulfate, is a negative allosteric modulator of the NMDA receptor, and also acts as a TRPM3 channel activator.