Allopregnanolone
From DrugPedia: A Wikipedia for Drug discovery
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==Description== | ==Description== | ||
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A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties. | A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties. | ||
'''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''', 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. | ||
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[edit] Description
A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties. 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.<ref>"Scientists find hormone activity explains adolescent mood swings" (Template:Dead link – Scholar search) . SUNY Downstate Medical Center.</ref>
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.
[edit] General Properties
*Molecular Weight
318.49
*Molecular Formula
C21H34O2
*IUPAC NAME
1-[(3R,5S,8R,9S,10S,13S,14S,17S)-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
*Canonical Smiles
CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
*Isomeric Smiles
CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C
[edit] PhysioChemical Properties
*Melting Point
*LogP
*Water Solubility
