ChemicalBook CAS DataBase List 1247-64-9

1247-64-9

Name	(3S,8S,9R,10S,13S,14R,17R)-17-acetyl-10,13-dimethyl-3-sulfooxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
CAS	1247-64-9
Molecular Formula	C21H32O5S
Molecular Weight	396.54
MOL File	1247-64-9.mol

Chemical Properties

density	1.25±0.1 g/cm3(Predicted)
storage temp.	Store at -20°C,stored under nitrogen
solubility	DMSO: 62.5 mg/mL (157.61 mM)
form	Solid
pka	-3.51±0.18(Predicted)
color	White to off-white

Hazard Information

Uses

Pregnenolone monosulfate (3β-Hydroxy-5-pregnen-20-one monosulfate) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone monosulfate acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone monosulfate can protect the brain from cannabis intoxication[1][2]. Pregnenolone monosulfate is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

Definition

ChEBI:Pregnenolone sulfate is a steroid sulfate. It has a role as an EC 2.7.1.33 (pantothenate kinase) inhibitor and a human metabolite. It is functionally related to a pregnenolone. It is a conjugate acid of a pregnenolone sulfate(1-).

in vivo

Pregnenolone administration (2-6 mg/kg) blocks THC-induced food-intake in Wistar rats and in C57BL/6N mice, and blunts the memory impairment induced by THC in mice, but it does not modify these behaviors per se. Injections of Pregnenolone (2 and 4mg/kg) before each self-administration session reduce the intake of WIN 55,212-2 and reduce the break-point in a progressive ratio schedule^[1].

IC 50

CB1; Human Endogenous Metabolite

storage

Store at -20°C,stored under nitrogen

References

[1] Vallée M, et al. Pregnenolone can protect the brain from cannabis intoxication. Science. 2014 Jan 3;343(6166):94-8. DOI:10.1126/science.1243985
[2] Ducharme N, et al. Brain distribution and behavioral effects of progesterone and pregnenolone after intranasal or intravenous administration. Eur J Pharmacol. 2010 Sep 1;641(2-3):128-34. DOI:10.1016/j.ejphar.2010.05.033
[3] Alan Shiels. TRPM3_miR-204: a complex locus for eye development and disease. Hum Genomics. 2020 Feb 18;14(1):7. DOI:10.1186/s40246-020-00258-4

Questions And Answer

Description
Pregnenolone sulfate is a neuroactive metabolite of pregnenolone. It has significant regulatory effects on the release of many important neurotransmitters such as glutamate, GABA, acetylcholine, norepinephrine, and dopamine.;
Discovery
The presence of high amounts of pregnenolone sulfate in the rat brain was reported, and it was found that the concentration of this sulfated steroid was not affected by adrenalectomy and castration.;
Regulation of synthesis and release
Neuropeptide Y inhibits the biosynthesis of pregnenolone sulfate in the frog hypothalamus through activation of the Y1 receptor.Gonadotropin-releasing hormone (GnRH) stimulates the biosynthesis of pregnenolone sulfate in the frog hypothalamus.;
Biological functions
Pregnenolone sulfate has multiple important effects on brain functions, such as cognitive enhancing, promnesic, antistress, and antidepressant effects.Pregnenolone sulfate also has significant regulatory effects on the release of many important neurotransmitters such as glutamate, GABA, acetylcholine, norepinephrine, and dopamine.;
Clinical implications
Central acetylcholine neurotransmission is known to be involved in the regulation of cognitive processes and is affected in normal aging and severely altered in human neurodegenerative pathologies such as Alzheimer’s disease.The level of acetylcholine cortical release induced by the infusion of pregnenolone sulfate was correlated to the spatial memory performance of animals.The infusion of pregnenolone sulfate stimulated the release of acetylcholine, suggesting that this effect could partly explain the memory-enhancing properties of this neurosteroid.;

Spectrum Detail

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