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516-55-2

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516-55-2 Usage

Description

Allopregnanolone is a neuroactive metabolite of progesterone. It is a potent positive allosteric modulator of the action of GABA on the GABAA receptor.

Properties

Mr of allopregnanolone is 318.49 and its melting point is 168°C.

Discovery

The presence of a progestational compound in the rabbit adrenal gland was reported in 1933, and was isolated in 1938 from the ox adrenal gland.Allopregnanolone formation was demonstrated in the brains of various vertebrates2–5 and the pineal glands of birds.

Biological functions

Allopregnanolone mediates its effects through modulation of the GABAA receptor.Allopregnanolone is reported to modulate the GABA-ergic function by increasing the GABAA receptor opening frequency and duration of the receptor at concentrations in the nanomolar range. A balance between unbinding, desensitization, and reopening of the desensitized GABAA receptor underlies the delay of the inhibitory postsynaptic currents.?Allopregnanolone slows the rate of recovery of the GABAA receptor from desensitization and possibly increases the rate of entry into fast desensitized states. Allopregnanolone exerts neurogenetic, neuroprotective, antidepressant, and anxiolytic effects. Reduced levels of allopregnanolone are found to be associated with major depression, anxiety disorders, premenstrual dysphoric disorder, and Alzheimer’s disease. Allopregnanolone is actively produced in the pineal gland compared with the brain and pineal allopregnanolone acts on Purkinje cells to prevent apoptosis in the juvenile quail.

Uses

Isopregnanolone is used in the preparation of antimicrobial and anti-leukemic steroids. Intermediate.

Clinical implications

Decreased production of allopregnanolone leads to NP-C; thus allopregnanolone treatment may be useful in ameliorating progression of the disease.In patients with Alzheimer’s disease, the level of allopregnanolone in the temporal cortex was significantly lower than controls, in contrast to pregnenolone and dehydroepiandrosterone where the concentrations were increased.This may be explained by altered regulation of the?neurosteroid biosynthetic pathway, which blocks allopregnanolone formation.

Regulation of synthesis and release

Allopregnanolone synthesis is stimulated by swim stress.In swim stress models, increased allopregnanolone is associated with decreased dopamine and norepinephrine in the prefrontal cortex, suggesting that allopregnanolone influences the mesolimbocortical dopamine pathway.In vivo treatment of the rat with the dopamine D4 antagonist clozapine induces a rapid increase in the concentration of allopregnanolone in the cerebral cortex and striatum.

Check Digit Verification of cas no

The CAS Registry Mumber 516-55-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 6 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 516-55:
(5*5)+(4*1)+(3*6)+(2*5)+(1*5)=62
62 % 10 = 2
So 516-55-2 is a valid CAS Registry Number.
InChI:InChI=1/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16+,17-,18-,19-,20+,21-/m1/s1

516-55-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 3β-hydroxy-5α-pregnan-20-one

1.2 Other means of identification

Product number -
Other names ALLOPREGNAN-3B-OL-20-ONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:516-55-2 SDS

516-55-2Relevant articles and documents

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Mancera et al.

, p. 1286,1289 (1953)

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Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation

Mikle, Gábor,Zugó, Alexandra,Szatnik, Erzsébet,Maxim, Anita,Mahó, Sándor,Kollár, László

, p. 1861 - 1867 (2021/01/05)

20-Carboxamidopregnene derivatives, such as 3β-acetoxy-5α-pregn-20-ene-20-carboxamides and 5α-pregn-20-ene-20-carboxamides were synthesized from the widely accessible 3β-acetoxy-pregn-5,16-dien-20-one (PDA) using selective hydrogenation, hydrazine and iodoalkene formation, as well as palladium-catalysed aminocarbonylation. The 20-iodo-20-ene derivatives, obtained from the corresponding 20-keto derivatives via their hydrazones, served as substrates. 23 new 20-carboxamides were obtained using various N-nucleophiles ranging from simple primary amines to α-amino acid esters. The novelty of this methodology lies in the application of facile, moderate or high-yielding reactions to obtain otherwise hardly accessible steroidal 20-carboxamides of pharmaceutical importance. In other words, instead of the enzymatic or synthetic degradation of e.g., sterols or cholanic acids, functionalization of the basic skeleton (a ‘building-up’ approach) was used.

COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS

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Paragraph 0579, (2021/01/23)

Provided herein is a compound of Formula I, II, IlIa, IlIb, V, VIa, VIb, VII, VIII, IX, or XI: or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising a compound of Formula I, II, IlIa, IlIb, V, VIa, VIb, VII, VIII, IX, or X, and methods of using the compounds, e.g., in the treatment of CNS-related disorders.

PROCESS FOR THE PREPARATION OF 3ALPHA-HYDROXY-5ΑLPHA-PREGNAN-20-ONE (BREXANOLONE)

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Page/Page column 12; 13, (2020/06/10)

The present invention relates to a new process for the synthesis of 3a-hydroxy-5a-pregnan-20-one, commonly known as brexanolone, wherein the corresponding cyclic 20-ketal or cyclic 20-thioketal compound of formula (IV) is deprotected with the use or iodine in an organic solvent: (I).

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