Allopregnanolone

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ImageFile=Allopregnanolone.pngImageSize=200px
IUPACName=1-(3-Hydroxy-10,13-dimethyl- 2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro- 1"H"-cyclopenta [a] phenanthren-17-yl)ethanone
OtherNames=3α,5α-Tetrahydroprogesterone
Section1= Chembox Identifiers
CASNo=516-54-1
PubChem=262961
SMILES= [H] [C@] 34 [C@] 2( [H] )CC [C@@] 1( [H] )C [C@H] (O)CC [C@@] (C)1 [C@] ( [H] )2CC [C@@] (C)3C(C(C)=O)CC4
Section2= Chembox Properties
Formula=C₂₁H₃₄O₂
MolarMass=318.49 g/mol
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Section3= Chembox Hazards
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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. [cite journal| url=http://www.downstate.edu/newsroom/news%20releases/2007/news_releases_full9.html| title=Scientists find hormone activity explains adolescent mood swings| journal=SUNY Downstate Medical Center| format=dead link|date=June 2008 – ^{[http://scholar.google.co.uk/scholar?hl=en&lr=&q=author%3A+intitle%3AScientists+find+hormone+activity+explains+adolescent+mood+swings&as_publication=SUNY+Downstate+Medical+Center&as_ylo=&as_yhi=&btnG=Search Scholar search]} ]

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

* cite book |last = Herd | first=MB, | coauthors = Belelli D, Lambert JJ.|title= Neurosteroid modulation of synaptic and extrasynaptic GABA(A) receptors|url= |format= |accessdate= |accessyear= |accessmonth= |edition= |date= 2007 |publisher= Pharmacol. Ther. 116(1):20-34 |location= |language= |id= |doi= 10.1016/j.pharmthera.2007.03.007