50588-47-1

Basic information

• Product Name: Amafolone
• Synonyms: Amafolone;3α-Amino-2β-hydroxy-5α-androstan-17-one
• CAS NO: 50588-47-1
• Molecular Formula: C19H31NO2
• Molecular Weight: 305.459
• Mol File: 50588-47-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 440.9 °C at 760 mmHg
• Flash Point: 220.5 °C
• Appearance: /
• Density: 1.109 g/cm³
• Refractive Index: 1.545
• CAS DataBase Reference: Amafolone(CAS DataBase Reference)
• NIST Chemistry Reference: Amafolone(50588-47-1)
• EPA Substance Registry System: Amafolone(50588-47-1)

Safety Data

• Hazardous Substances Data: 50588-47-1(Hazardous Substances Data)

Usage

Originator

Amafolone hydrochloride,ZYF Pharm Chemical

Manufacturing Process

A solution of 70% perchloric acid (60 ml) in water (280 ml) was added to a stirred solution of 5α-androst-2-en-17-one (200.0 g) in ether (1.15 l) at 15°C followed by portionwise addition of N-bromacetamide (112.0 g) over 10 min. After stirring for 1 h the precipitated white crystalline solid was filtered off, washed neutral with ether and water and crystallised to give 2β-hydroxy-3α- bromo-5α-androstan-17-one (172.0 g). The ether layer of the filtrate was washed neutral, dried (Na2SO4) and concentrated to give a second crop (28.0 g). The two crops (200.0 g) were suspended in methanol (1 L), 10 N aqueous potassium hydroxide solution (100 ml) added and the mixture slowly distilled over 45 min. Addition of water precipitated the product as a white solid which was filtered off, washed with water, dried and 88.0 g of 2β,3β-epoxy-5α- androstan-17-one were obtained (crystallisation from ether:light petrol). A solution of the 2β,3β-epoxy-5α-androstan-17-one (30.0 g) in ethanol (130 ml), water (15 ml) and liquid ammonia was heated in an autoclave at 150°C for 6 h and the resultant crystalline suspension evaporated to dryness. Water (35 ml) and acetic acid (36 ml) were added and the solution kept at 90°C for 1 h, cooled and excess water added. The precipitated material was filtered off and the filtrate made alkaline with aqueous 10 N potassium hydroxide solution to precipitate a white solid which was filtered off, washed neutral with water, dissolved in methylene chloride, the solution dried (Na2SO4) concentrated and ether added to give 2β-hydroxy-3α-amino-5α-androstan-17-one (14.3 g), melting point l92°-195°C. In practice it is usually used as hydrochloride.

Therapeutic Function

Antiarrhythmic

InChI:InChI=1/C19H31NO2/c1-18-8-7-14-12(13(18)5-6-17(18)22)4-3-11-9-15(20)16(21)10-19(11,14)2/h11-16,21H,3-10,20H2,1-2H3/t11?,12-,13?,14?,15-,16-,18-,19-/m0/s1

Upstream product

• 965-67-3 2β,3-Oxido-5α-androstan-17-one 
• 27489-84-5 3α-Azido-5α-androstan-2β-ol-17-one 
• 14639-79-3 5α-androst-2-en-17-one 
• 7676-27-9 3α-Bromo-5α-androstan-2β-ol-one 

Relevant articles and documents

SYNTHESIS AND ANTIARRHYTHMIC ACTIVITY OF 3 &α-AMINO-5-&α-ANDROSTAN-2-&β-OL-17-ONE

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