Names | |
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IUPAC name
20-Oxopregn-5-en-3β-yl hydrogen sulfate
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Systematic IUPAC name
(1S,3aS,3bS,7S,9aR,9bS,11aS)-1-Acetyl-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl hydrogen sulfate | |
Other names
Pregn-sulf; Pregnenolone monosulfate; Pregnenolone hydrogen sulfate; Pregnenolone 3β-sulfate; 5-Pregnen-3β-ol-20-one sulfate; (3β)-3-(Sulfooxy)pregn-5-en-20-one; 5-Pregnen-3β-sulfate-20-one; 20-Oxo-5-pregnen-3β-yl sulfate
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Identifiers | |
3D model (
JSmol)
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ChEMBL | |
ChemSpider | |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C21H32O5S | |
Molar mass | 396.54 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Pregnenolone sulfate (PS, PREGS) is an endogenous excitatory neurosteroid that is synthesized from pregnenolone. [1] [2] It is known to have cognitive and memory-enhancing, antidepressant, anxiogenic, and proconvulsant effects. [2]
Pregnenolone sulfate is a neurosteroid with excitatory effects in the brain, acting as a potent negative allosteric modulator of the GABAA receptor and a weak positive allosteric modulator of the NMDA receptor. [1] [2] To a lesser extent, it also acts as a negative allosteric modulator of the AMPA, kainate, and glycine receptors, [3] [4] and may interact with the nACh receptors as well. [1] In addition to its effects on ligand-gated ion channels, pregnenolone sulfate is an agonist of the sigma receptor, [2] as well as an activator of the TRPM1 and TRPM3 channels. [1] It may also interact with potassium channels and voltage-gated sodium channels [1] and has been found to inhibit voltage-gated calcium channels. [5]
Pregnenolone sulfate is synthesized from pregnenolone via sulfation. Pregnenolone itself is produced from cholesterol via cholesterol side-chain cleavage enzyme.
Pregnenolone sulfate, also known as pregn-5-en-3β-ol-20-one 3β-sulfate, is a naturally occurring pregnane steroid and a derivative of cholesterol. It is the C3β sulfate ester of pregnenolone. A closely related steroid is dehydroepiandrosterone sulfate (DHEA-S), which is the C3β sulfate ester of dehydroepiandrosterone (DHEA).
Names | |
---|---|
IUPAC name
20-Oxopregn-5-en-3β-yl hydrogen sulfate
| |
Systematic IUPAC name
(1S,3aS,3bS,7S,9aR,9bS,11aS)-1-Acetyl-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl hydrogen sulfate | |
Other names
Pregn-sulf; Pregnenolone monosulfate; Pregnenolone hydrogen sulfate; Pregnenolone 3β-sulfate; 5-Pregnen-3β-ol-20-one sulfate; (3β)-3-(Sulfooxy)pregn-5-en-20-one; 5-Pregnen-3β-sulfate-20-one; 20-Oxo-5-pregnen-3β-yl sulfate
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C21H32O5S | |
Molar mass | 396.54 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Pregnenolone sulfate (PS, PREGS) is an endogenous excitatory neurosteroid that is synthesized from pregnenolone. [1] [2] It is known to have cognitive and memory-enhancing, antidepressant, anxiogenic, and proconvulsant effects. [2]
Pregnenolone sulfate is a neurosteroid with excitatory effects in the brain, acting as a potent negative allosteric modulator of the GABAA receptor and a weak positive allosteric modulator of the NMDA receptor. [1] [2] To a lesser extent, it also acts as a negative allosteric modulator of the AMPA, kainate, and glycine receptors, [3] [4] and may interact with the nACh receptors as well. [1] In addition to its effects on ligand-gated ion channels, pregnenolone sulfate is an agonist of the sigma receptor, [2] as well as an activator of the TRPM1 and TRPM3 channels. [1] It may also interact with potassium channels and voltage-gated sodium channels [1] and has been found to inhibit voltage-gated calcium channels. [5]
Pregnenolone sulfate is synthesized from pregnenolone via sulfation. Pregnenolone itself is produced from cholesterol via cholesterol side-chain cleavage enzyme.
Pregnenolone sulfate, also known as pregn-5-en-3β-ol-20-one 3β-sulfate, is a naturally occurring pregnane steroid and a derivative of cholesterol. It is the C3β sulfate ester of pregnenolone. A closely related steroid is dehydroepiandrosterone sulfate (DHEA-S), which is the C3β sulfate ester of dehydroepiandrosterone (DHEA).