Allopregnanolone

Base Information

• Chemical Name: Allopregnanolone
• CAS No.: 516-54-1
• Molecular Formula: C21H34O2
• Molecular Weight: 318.5
• European Community (EC) Number: 869-372-7
• UNII: S39XZ5QV8Y
• DSSTox Substance ID: DTXSID901016239
• Nikkaji Number: J6.315K
• Wikipedia: Allopregnanolone
• Wikidata: Q2482223
• NCI Thesaurus Code: C169815
• RXCUI: 2121777
• Metabolomics Workbench ID: 35435
• ChEMBL ID: CHEMBL207538
• Mol file: 516-54-1.mol

Synonyms:3 alpha Hydroxy 5 alpha pregnan 20 one;3 alpha Hydroxy 5 beta pregnan 20 one;3 alpha, 5 beta Tetrahydroprogesterone;3 alpha, 5 beta-Tetrahydroprogesterone;3 alpha-Hydroxy-5 alpha-pregnan-20-one;3 alpha-Hydroxy-5 beta-pregnan-20-one;3 Hydroxypregnan 20 one;3-Hydroxypregnan-20-one;3beta Hydroxy 5alpha pregnan 20 one;3beta-Hydroxy-5alpha-pregnan-20-one;Allopregnan 3 beta ol 20 one;Allopregnan-3 beta-ol-20-one;Allopregnanolone;alpha-Hydroxy-5 alpha-pregnan-20-one, 3;alpha-Hydroxy-5 beta-pregnan-20-one, 3;alpha-pregnan-20-one, 3 alpha-Hydroxy-5;beta-ol-20-one, Allopregnan-3;beta-pregnan-20-one, 3 alpha-Hydroxy-5;Eltanolone;Epipregnanolone;Pregnan 3alpha ol 20 one;Pregnan-3alpha-ol-20-one;Pregnanolone;Pregnanolone, (3alpha)-isomer;Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer;Pregnanolone, (3alpha,5alpha)-isomer;Pregnanolone, (3alpha,5beta)-isomer;Pregnanolone, (3beta)-isomer;Pregnanolone, (3beta, 5alpha)-isomer;Pregnanolone, (3beta, 5alpha, 17alpha)-isomer;Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer;Pregnanolone, (3beta, 5beta)-isomer;Pregnanolone, (3beta, 5beta, 17alpha)-isomer;Pregnanolone, (3beta, 5beta,14beta)-isomer;Pregnanolone, (5alpha)-isomer;Sepranolone

Chemical Property of Allopregnanolone

Chemical Property:

• Vapor Pressure: 3.05E-09mmHg at 25°C
• Melting Point: 176-178°
• Refractive Index: 1.524
• Boiling Point: 431.2°Cat760mmHg
• PKA: 15.12±0.70(Predicted)
• Flash Point: 183.9°C
• PSA: 37.30000
• Density: 1.053g/cm³
• LogP: 4.59520
• Storage Temp.: Store at RT
• Solubility.: chloroform: 20 mg/mL, clear, colorless
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 318.255880323
• Heavy Atom Count: 23
• Complexity: 500

Purity/Quality:

99%-101% ^*data from raw suppliers

(3α)-Allopregnanolone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C
• Recent ClinicalTrials: An Open-Label Study Evaluating Brexanolone in Adults With Tinnitus
• Recent EU Clinical Trials: A RANDOMIZED, DOUBLE-BLIND, PLACEBO-CONTROLLED STUDY TO EVALUATE THE EFFICACY AND SAFETY OF SAGE-547 INJECTION IN THE TREATMENT OF SUBJECTS WITH SUPER-REFRACTORY STATUS EPILEPTICUS
• Description: Allopregnanolone is an endogenous inhibitory pregnane neurosteroid that is synthesized from progesterone . It acts as a positive allosteric modulator of GABAA receptors at nM concentrations (exhibiting the greatest potentiation at isoforms containing δ subunits) and of GABAC receptors at μM concentrations. Allopregnanolone displays effects similar to other GABAA receptor potentiators such as benzodiazepines, including potent anticonvulsant, anxiolytic, and sedative activity.
• Uses: (3α)-Allopregnanolone acts as a GABAA receptor positive allosteric modulator. (3α)-Allopregnanolone is a metabolite of Progesterone (P755900). (3α)-Allopregnanolone is a neuroactive steroid present in the blood and also the brain.

Technology Process of Allopregnanolone

There total 11 articles about Allopregnanolone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 32.5%

dihydroprogesterone (566-65-4) → isopregnanolone (516-55-2) + tetrahydroprogesterone (516-54-1)

Guidance literature:

With trimethylamine-borane; silica gel; iron(III) chloride; In benzene; for 2h; Product distribution; Ambient temperature; various catalysts and times;

DOI:10.1246/cl.1986.61

Reference yield:

pregnanedione (128-23-4) → pregnadiol (80-89-7,80-90-0,80-92-2,516-53-0,566-56-3,566-57-4,566-58-5,4406-36-4,4479-11-2,4707-80-6,6251-84-9,25908-35-4,28818-70-4,36027-66-4,38270-91-6,38270-97-2,52746-43-7,55569-11-4,55660-10-1,73745-18-3,98048-13-6,80-91-1) + PREGNANOLONE (128-20-1,128-21-2,516-54-1,516-55-2,4243-94-1,4320-08-5,4406-35-3,4406-37-5,4469-03-8,13089-85-5,13089-86-6,14615-01-1,21788-58-9,24557-99-1,25126-79-8,26961-00-2,36027-63-1,39845-99-3,40135-22-6,72691-57-7,81076-02-0,95118-68-6,110350-90-8)

Guidance literature:

With recombinant human aldo-keto reductase 1C₃; NADPH; In methanol; at 37 ℃; for 1.5h; pH=7; stereospecific reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1042/BJ20101804

Reference yield:

Progesterone (57-83-0) → pregnanedione (128-23-4) + 3β-hydroxy-5β-pregnan-20-one (128-21-2) + pregnanediol (80-92-2) + pregnadiol (80-89-7,80-90-0,80-92-2,516-53-0,566-56-3,566-57-4,566-58-5,4406-36-4,4479-11-2,4707-80-6,6251-84-9,25908-35-4,28818-70-4,36027-66-4,38270-91-6,38270-97-2,52746-43-7,55569-11-4,55660-10-1,73745-18-3,98048-13-6,80-91-1) + PREGNANOLONE (128-20-1,128-21-2,516-54-1,516-55-2,4243-94-1,4320-08-5,4406-35-3,4406-37-5,4469-03-8,13089-85-5,13089-86-6,14615-01-1,21788-58-9,24557-99-1,25126-79-8,26961-00-2,36027-63-1,39845-99-3,40135-22-6,72691-57-7,81076-02-0,95118-68-6,110350-90-8) + 3α-hydroxy-5β-pregnane-20-one-3-glucuronide (31329-54-1)

Guidance literature:

With phosphate buffer; (S)-2-[3]pyridyl-pyrrolidine-1-carboxylic acid amide; α-D-glucose 6-phosphate; bovine liver tissue supernatant; NADP; UDP-glucuronic acid; at 37 ℃; for 5h; Product distribution; <14C>labeled;

DOI:10.1016/0039-128X(82)90041-1

upstream raw materials:

dihydroprogesterone

Progesterone

hydrogen bromide

acetic acid

Downstream raw materials:

dihydroprogesterone

androstanediol

pregnanediol

pregnadiol

Refernces

• 1、 -. "METHODS OF NEUROPROTECTION USING NEUROPROTECTIVE STEROIDS AND A VITAMIN D". . . Retrieved 2012/01/03.
• 2、 Leontjev,Vasiljeva,Pivnitsky. "Reduction of steroidal ketones with amine - Boranes". . p. 703 - 708. Retrieved 2007/10/03.