Allopregnanolone

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Allopregnanolone
IUPAC name 1-(3-Hydroxy-10,13-dimethyl-
2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-
1H-cyclopenta[a]
phenanthren-17-yl)ethanone
Other names 3α,5α-Tetrahydroprogesterone
Identifiers
CAS number [516-54-1]
PubChem 262961
SMILES
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.

Allopregnanolone targets the GABA A receptor to reduce anxiety and create calm at times of stress. The hormone allopregnanolone normally released in response to stress, actually reverses its effect at puberty and instead increases anxiety.[1]

The 3β enantiomer 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.

References

  1. ^ "Scientists find hormone activity explains adolescent mood swings" (dead linkScholar search) . SUNY Downstate Medical Center. 


* 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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  • This page was last modified on 17 July 2008, at 06:25.

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