Pregnenolone

Names

[ CAS No. ]:
145-13-1

[ Name ]:
Pregnenolone

[Synonym ]:
EINECS 205-647-4
prenolon
ZK-5553
MFCD00003628
Pregn-5-en-20-one, 3-hydroxy-
prenenolone
Pregnelone
Pregnenlolone
3-Hydroxypregn-5-en-20-one
Pregnenolone
3β-Hydroxy-5-pregnen-20-one
5-Pregnen-3β-ol-20-one
pregnolon
Progeserone

Biological Activity

[Description]:

Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, reduces several effects of tetrahydrocannabinol (THC).

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor

Research Areas >> Neurological Disease

Natural Products >> Steroids

[Target]

CB1 Receptor

Human Endogenous Metabolite

[In Vitro]

The effect of THC is significantly attenuated when slices are pre-treated with Pregnenolone 100 nM (15.1±1.8 % of inhibition). These effects are likely due to a pre-synaptic action of Pregnenolone. Thus, Pregnenolone blocks the increase in paired-pulse ratio (PPR) induced by THC but does not modify either the amplitude or the decay time of miniature EPSC (mEPSC)[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].

[Animal admin]

Mice and Rats[1] Adult male Wistar rats (weighing 320-340g), Sprague Dawley male rats (weighing 330-350g), C57BL/6N mice (2-3 months) and CD1 mice (weighing 25-30 g at the beginning of the experiments) are used. Pregnenolone is injected subcutaneously (sc). The injection volumes are 1 mL/kg of body weight for rats and 10 mL/kg for mice[1].

[References]

[1]. Vallée M, et al. Pregnenolone can protect the brain from cannabis intoxication. Science. 2014 Jan 3;343(6166):94-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
443.3±45.0 °C at 760 mmHg

[ Melting Point ]:
188-190 °C

[ Molecular Formula ]:
C₂₁H₃₂O₂

[ Molecular Weight ]:
316.478

[ Flash Point ]:
188.9±21.3 °C

[ Exact Mass ]:
316.240234

[ PSA ]:
37.30000

[ LogP ]:
4.52

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.550

[ Storage condition ]:
2~8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TU5560700

CHEMICAL NAME :: Pregn-5-en-20-one, 3-beta-hydroxy-

CAS REGISTRY NUMBER :: 145-13-1

LAST UPDATED :: 199609

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C21-H32-O2

MOLECULAR WEIGHT :: 316.53

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 11,117,1968 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 35 mg/kg

SEX/DURATION :: female 7 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: JEMEAV Journal of Experimental Medicine. (Rockefeller Univ. Press, 1230 York Ave., New York, NY 10021) V.1- 1896- Volume(issue)/page/year: 102,347,1955

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302 + H312 + H332-H319

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
TU5560700

[ HS Code ]:
2937290090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2937290090

Articles

Mechanistic Scrutiny Identifies a Kinetic Role for Cytochrome b5 Regulation of Human Cytochrome P450c17 (CYP17A1, P450 17A1).

PLoS ONE 10 , e0141252, (2015)

Cytochrome P450c17 (P450 17A1, CYP17A1) is a critical enzyme in the synthesis of androgens and is now a target enzyme for the treatment of prostate cancer. Cytochrome P450c17 can exhibit either one or...

HBCDD-induced sustained reduction in mitochondrial membrane potential, ATP and steroidogenesis in peripubertal rat Leydig cells.

Toxicol. Appl. Pharmacol. 282(1) , 20-9, (2015)

Hexabromocyclododecane (HBCDD), a brominated flame retardant added to various consumer products, is a ubiquitous environmental contaminant. We have previously shown that 6-hour exposure to HBCDD distu...

Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk).

J. Med. Chem. 48 , 3269-79, (2005)

Growing interest in the use of both the logarithm of the partition coefficient of the neutral species in the alkane/water system (log P(N)(alk)) and the difference between log P(N)(oct) (the logarithm...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.