5035-10-9

Basic information

• Product Name: (20S)-20-Aminopregn-5-en-3β-ol
• Synonyms: (20S)-20-Aminopregn-5-en-3β-ol;Holafebrine
• CAS NO: 5035-10-9
• Molecular Formula: C21H35NO
• Molecular Weight: 317.5087
• Mol File: 5035-10-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 172-174 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 440.5°C at 760 mmHg
• Flash Point: 220.2°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 1.3E-09mmHg at 25°C
• Refractive Index: 1.557
• PKA: 15.03±0.70(Predicted)
• CAS DataBase Reference: (20S)-20-Aminopregn-5-en-3β-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (20S)-20-Aminopregn-5-en-3β-ol(5035-10-9)
• EPA Substance Registry System: (20S)-20-Aminopregn-5-en-3β-ol(5035-10-9)

Safety Data

• Hazardous Substances Data: 5035-10-9(Hazardous Substances Data)

Usage

Description

(20S)-20-Aminopregn-5-en-3β-ol, also known as 20-aminopregnenolone, is a steroidal molecule that is a derivative of pregnenolone, which is a precursor to various steroid hormones in the body. It has a chemical structure similar to progesterone and is a neurosteroid that acts on the central nervous system. (20S)-20-Aminopregn-5-en-3β-ol has been studied for its potential neuroprotective and anti-inflammatory properties, and has shown promise in animal models for the treatment of conditions such as traumatic brain injury and spinal cord injury. It is also being investigated for its potential role in the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's. Overall, (20S)-20-Aminopregn-5-en-3β-ol has potential therapeutic applications in the field of neuroscience and neurology.

Uses

Used in Neuroscience and Neurology:
(20S)-20-Aminopregn-5-en-3β-ol is used as a neuroprotective and anti-inflammatory agent for the treatment of traumatic brain injury and spinal cord injury. Its neuroprotective properties have shown promise in animal models, and it is being investigated for its potential role in the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's.

InChI:InChI=1/C21H35NO/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/h4,13,15-19,23H,5-12,22H2,1-3H3/t13-,15-,16-,17+,18-,19-,20-,21+/m0/s1

Upstream product

• 145-13-1 Pregnenolone 
• 40521-49-1 20α-aminopregn-5-en-3β-ol 3-THP ether 
• 6192-84-3 δ⁵-pregnen-3β-ol-20-one oxime 
• 104015-56-7 20α-acetamidopregn-5-en-3β-ol acetate 

Downstream Products

• 2309-39-9 (+)-irehine 
• 3915-24-0 20S,22-azacholesterol 
• 7083-27-4 20α-amino-5-pregnen-3β-ol 
• 17541-67-2 20α_F-benzylidenamino-pregnen-(5)-ol-(3β) 

Relevant articles and documents

Crystal and molecular structures of (20R)-20-aminopregn-5-en-3β-ol and (20S)-20-aminopregn-5-en-3β-ol hydrochloride

Two epimers of 20-aminopregn-5-en-3β-ol differing in configuration at C(20) have been synthesized and their structures have been determined by single crystal X-ray diffraction methods. The (20R)-epimer (1) crystallized in the orthorhombic system, space group P212121, with a = 9.0432(5) A, b = 13.3446(7) A, c = 15.1086(8) A, and Z = 4. The (20S)-epimer hydrochloride hydrate (2 hydrate) crystallized in the monoclinic system, space group C2, with a = 31.0501(3) A, b = 11.8221(1) A, c = 11.9703(2) A, β = 98.5140(10)o, and Z = 8. The absolute configurations at the C(20) chiral centers for the title compounds were unequivocally established for the first time. The asymmetric unit cell of 2 hydrate contained two steroid molecules, A and B, two hydrochloride molecules, and two molecules of water. The crystal packing for both diastereomers was strongly influenced by the presence of intermolecular hydrogen bonding. The molecules of 1 were linked in a head-to-tail fashion via hydrogen bonds between the hydroxyl group of the ring A and the amino group of the side chain of the ring D. The two molecules A and B of 2 hydrate were held together in head-to-head and head-to-tail fashions by a three-dimensional network of hydrogen bonds involving chlorine ions, disordered water molecules, and hydroxyl - amino groups interactions.

STEROIDAL N-NITROAMINES. PART 4. INTRAMOLECULAR FUNCTIONALIZATION OF N-NITROAMINE RADICALS: SYNTHESIS OF 1,4-NITROIMINE COMPOUNDS

Photolysis of 6β-nitroamino-5α-cholestane (4), 6β-nitroamino-5α-cholestane-3β-yl acetate (5), 2β-nitroamino-5α-cholestane (13), 4β-nitroamino-5α-cholestane (17), (20R)-20 nitroaminopregm-5-en-3β-yl acetate (26), (20R)- (31) and (20S)- (34)-nitroamino-5α-pregnan-3β-yl acetate, (23R,25S)-3β-acetoxy-23-nitroamino-5β-spirostan (46), 3β-nitroaminofriedelane (53), and methyl 3β-nitroaminofriedelan-29-oate (54) in the presence of iodine and various oxidative reagents leads to neutral nitroaminyl radicals which undergo intramolecular hydrogen-abstraction to produce in most cases N-nitroimine compounds.Best results were obtained with the system iodine and (diacetoxyiodo)benzene.

Inhibition of cholesterol side-chain cleavage. 2. Synthesis of epimeric azacholesterols.

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