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

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