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| 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) | |
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| Properties | |
| C21H32O5S | |
| Molar mass | 396.54 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Pregnenolone sulfate (PS,PREGS) is anendogenousexcitatoryneurosteroid that issynthesized frompregnenolone.[1][2] It is known to havecognitive andmemory-enhancing,antidepressant,anxiogenic, andproconvulsant effects.[2]
Pregnenolone sulfate is a neurosteroid with excitatory effects in the brain, acting as a potentnegative allosteric modulator of theGABAA receptor and a weakpositive allosteric modulator of theNMDA receptor.[1][2] To a lesser extent, it also acts as a negative allosteric modulator of theAMPA,kainate, andglycine receptors,[3][4] and may interact with thenACh receptors as well.[1] In addition to its effects onligand-gated ion channels, pregnenolone sulfate is anagonist of thesigma receptor,[2] as well as anactivator of theTRPM1 andTRPM3 channels.[1] It may also interact withpotassium channels andvoltage-gated sodium channels[1] and has been found to inhibitvoltage-gated calcium channels.[5]
Pregnenolone sulfate issynthesized frompregnenolone viasulfation. Pregnenolone itself is produced fromcholesterol viacholesterol side-chain cleavage enzyme.
Pregnenolone sulfate, also known as pregn-5-en-3β-ol-20-one 3β-sulfate, is anaturally occurringpregnanesteroid and aderivative ofcholesterol. It is the C3βsulfateester ofpregnenolone. A closely related steroid isdehydroepiandrosterone sulfate (DHEA-S), which is the C3β sulfate ester ofdehydroepiandrosterone (DHEA).
