25447-66-9

Basic information

• Product Name: dihydroergocryptine
• Synonyms: dihydroergocryptine;9,10α-Dihydro-12'-hydroxy-2'-(1-methylethyl)-5'α-(2-methylpropyl)ergotaman-3',6',18-trione;9,10α-Dihydro-12'-hydroxy-2'-isopropyl-5'α-(2-methylpropyl)ergotaman-3',6',18-trion;9,10α-Dihydro-12'-hydroxy-2'-isopropyl-5'α-isobutylergotaman-3',6',18-trione;Dihydroergokryptine;(5'α,10α)-9,10-Dihydro-12'-hydroxy-2'-(1-Methylethyl)-5'-(2-Methylpropyl)ergotaMan-3',6',18-trione;9,10-Dihydroergocryptine;9,10-Dihydroergokryptine
• CAS NO: 25447-66-9
• Molecular Formula: C₃₂H₄₃N₅O₅
• Molecular Weight: 577.71432
• EINECS: 246-993-6
• Product Categories: Aromatics, Heterocycles, Inhibitors, Neurochemicals, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 25447-66-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 235 °C (decomp)
• Boiling Point: 848.7°C at 760 mmHg
• Flash Point: 467.1°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 1.26E-30mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
• PKA: pKa 6.89±0.07(H2O t=24 I≤0.01) (Uncertain)
• Stability: Hygroscopic
• CAS DataBase Reference: dihydroergocryptine(CAS DataBase Reference)
• NIST Chemistry Reference: dihydroergocryptine(25447-66-9)
• EPA Substance Registry System: dihydroergocryptine(25447-66-9)

Safety Data

• Hazardous Substances Data: 25447-66-9(Hazardous Substances Data)

Usage

Uses

Dihydro α-Ergocryptine is a hydrogenated ergot alkaloids, specifically an equiproportional mixture of dihydroergocornine methanesulfonate, dihydroergocristine methanesulfonate, α and β-dihydroergocrytine methanesulfonate in the ratio of 1.5-2.5:1. Dihydro α-Ergocryptine is an α-adrenergic blocker used for the treatment of impaired mental function in the elderly.

Definition

ChEBI: alpha-Ergocryptine in which a single bond replaces the double bond between positions 9 and 10.

InChI:InChI=1/C32H43N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38)/t20-,22-,24-,25+,26+,31-,32+/m1/s1

Upstream product

• 511-09-1 α-ergocryptine 

Downstream Products

• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 30341-92-5 methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate 
• 72821-79-5 methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate 
• 81409-74-7 (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid 
• 85329-86-8 (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide 
• 126554-50-5 (6aR,9R,10aR)-7-allyl-N⁹-[3-(dimethylamino)propyl]-N⁴-ethyl-N⁹-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide 
• 5878-43-3 9,10-dihydrolysergic acid 

Relevant articles and documents

Synthesis of European pharmacopoeial impurities A, B, C, and D of cabergoline

For the use of analytics, European pharmacopoeial impurities A, B, C, and D of cabergoline were synthesized. Ergocryptine was chosen as a starting material and synthesis was accomplished via two approaches, different in length and stereochemical outcome. A longer, indirect approach was realized through otherwise problematic oxidations of the 9,10-dihidrolysergol derivative, to the corresponding aldehyde and carboxylic acid. This was achieved by the use of activated DMSO and a Pinnick oxidation sequence. All four synthesized impurities are used as analytical standards in cabergoline manufacturing processes.