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Allopregnanolone
Identifiers
CAS number 516-54-1
PubChem 262961
ChemSpider 17216124
SMILES
InChI
InChI key AURFZBICLPNKBZ-JMTGGFPBBC
Properties
Molecular formula C21H34O2
Molar mass 318.49 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Allopregnanolone, also known as 3α,5α-tetrahydroprogesterone or THP, is an important neurosteroid in the human brain. It is a metabolite of progesterone and a barbiturate-like modulator of central gamma-aminobutyric acid (GABA) receptors that modify a range of behaviors, including the stress response.

The 5β epimer of this compound is known as pregnanolone, and has very similar properties to allopregnanolone. Both compounds are found endogenously and have similar hypnotic and anxiolytic effects.

The production of allopregnanolone starts with 5-alpha-reductase converting progesterone into pregnanolone. After that, 3beta-hydroxy-5alpha-steroid dehydrogenase converts the former into allopregnanolone.

References

* Herd, MB,; Belelli D, Lambert JJ. (2007). Neurosteroid modulation of synaptic and extrasynaptic GABA(A) receptors. Pharmacol. Ther. 116(1):20-34. doi:10.1016/j.pharmthera.2007.03.007. 
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