| Identification | Back Directory | [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 | [Synonyms]
Pregnenolone sulfate
Pregnenolone sulphate
Pregnenolone monosulfate
DIJBBUIOWGGQOP-OZIWPBGVSA-N
3β-Hydroxy-5-pregnen-20-one monosulfate
Pregn-5-en-20-one, 3-(sulfooxy)-, (3β)-
Di[(pregn-5-en-20-one)-3-yl] =sulfate ester
(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 | [Molecular Formula]
C21H32O5S | [MOL File]
1247-64-9.mol | [Molecular Weight]
396.54 |
| Questions And Answer | Back Directory | [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. |
| Chemical Properties | Back Directory | [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 | Back Directory | [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 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
(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(1247-64-9)1HNMR
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Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
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