Alloepipregnanolone

Names

[ CAS No. ]:
516-55-2

[ Name ]:
Alloepipregnanolone

[Synonym ]:
ALLOPREGNAN-3B-OL-20-ONE
3beta-hydroxy-5alpha-pregnan-20-one
3-Hydroxypregnan-20-one
Alloepipregnanolone
5A-PREGNAN-3B-OL-20-ONE
Tetrahydroprogesterone
ALLOPREGNANOLONE
ISOPREGNANOLONE
EINECS 208-224-2
MFCD00064935
Pregnan-20-one,3-hydroxy-, (3b,5a)-
epi-allopregnanolone

Biological Activity

[Description]:

Alloepipregnanolone, a pregnane with anesthetic, hypnotic, and sedative properties, interferes with the development of rapid tolerance to the anxiolytic effect of ethanol.

[Related Catalog]:

Research Areas >> Metabolic Disease

Natural Products >> Others

[Target]

Human Endogenous Metabolite

[In Vivo]

On day 2, pretreatment with a 0.20 mg/kg dose of Alloepipregnanolone blocks the development of rapid tolerance to the anxiolytic effect of ethanol. However, there is a significant decrease in the anxiolytic effect in the control groups that received ethanol on both days (EE), suggesting that the 1.5 g/kg dose of ethanol results in rapid tolerance. The post hoc analysis confirms that the 0.20 mg/kg pretreatment with Alloepipregnanolone blocks the rapid tolerance compared to the control groups, although the 0.10 mg/kg dose only partially blocks the development of such tolerance. However, the 0.05 mg/kg dose has no effect on the development of rapid tolerance to ethanol[1].

[Animal admin]

Mice[1] Male Swiss mice are pretreated with Alloepipregnanolone (isopregnanolone: 0.05, 0.10 or 0.20 mg/kg) 30 min before administration of ethanol (1.5 g/kg). Twenty-four hours later, all animals tested using the plus-maze apparatus. The first experiment defines the doses of ethanol that does or does not induce rapid tolerance to the anxiolytic effect of ethanol. In the second, the influence of pretreatment of mice with Alloepipregnanolone (0.05, 0.10 or 0.20 mg/kg) on rapid tolerance to ethanol (1.5 g/kg) is studied[1].

[References]

[1]. Debatin T, et al. Effect of isopregnanolone on rapid tolerance to the anxiolytic effect of ethanol. Rev Bras Psiquiatr. 2006 Mar;28(1):18-23.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.053g/cm3

[ Boiling Point ]:
431.2ºC at 760mmHg

[ Melting Point ]:
200℃

[ Molecular Formula ]:
C₂₁H₃₄O₂

[ Molecular Weight ]:
318.49300

[ Flash Point ]:
183.9ºC

[ Exact Mass ]:
318.25600

[ PSA ]:
37.30000

[ LogP ]:
4.59520

[ Index of Refraction ]:
1.524

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TU4383200

CHEMICAL NAME :: 5-alpha-Pregnan-20-one, 3-beta-hydroxy-

CAS REGISTRY NUMBER :: 516-55-2

LAST UPDATED :: 199709

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H34-O2

MOLECULAR WEIGHT :: 318.55

WISWESSER LINE NOTATION :: L E5 B666TJ A1 E1 FV1 OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 40 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

Safety Information

[ RTECS ]:
TU4383200

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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