3 β- hydroxypregn-5-en-20-one
|Molecular formula||C 21 H 32 O 2|
|External identifiers / databases|
|Molar mass||316.48 g mol −1|
193 ° C
almost insoluble in water (7.06 mg l −1 at 37 ° C)
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .|
Pregnenolone is formed from cholesterol by hydroxylation at C 20 and C 22 with subsequent cleavage of the side chain . The conversion is catalyzed by the enzyme cholesterol monooxygenase in the mitochondria and controlled by the pituitary hormones ACTH , FSH , LH .
The necessary transport of cholesterol from the cytosol into the mitochondria takes place by binding to the StAR protein , a transport protein in the mitochondrial membrane. Nothing is yet known about the exact transport of pregnenolone from the mitochondria.
Use and therapeutic effectiveness
In animal experiments on mice and rats, pregnenolone blocks the activation of the cannabinoid receptor type 1 (CB1). a. is activated by ∆ 9 - tetrahydrocannabinol (THC), the main active ingredient of hemp ( Cannabis sativa ). It could thus act as an antagonist .
- Entry on pregnenolone. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.
- Entry on pregnenolone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
- Data sheet 5-Pregnen-3β-ol-20-one from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).
- Pregnenolone biosynthesis on Reactome.Org (R-HSA-196108), accessed July 28, 2020
- Antidote to cannabis high discovered. Der Standard, January 3, 2014, accessed January 5, 2014 .
- M. Vallee, S. Vitiello et al. a .: Pregnenolone Can Protect the Brain from Cannabis Intoxication. In: Science. 343, 2014, pp. 94–98, doi : 10.1126 / science.1243985 .