81409-74-7

Basic information

• Product Name: 6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID
• Synonyms: 6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID;(8b)-6-Allylergoline-8-carboxylic acid;6-(2-Propenyl)dihydrolysergic acid;6-Allyl-8β-carboxyergoline;Cabergoline impurity A -d;YAICYXFUKKMAKO-XNRPHZJLSA-N
• CAS NO: 81409-74-7
• Molecular Formula: C₁₈H₂₀N₂O₂
• Molecular Weight: 296.36
• Mol File: 81409-74-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 530.4 °C at 760 mmHg
• Flash Point: 274.6 °C
• Appearance: /
• Density: 1.258
• Vapor Pressure: 4.45E-12mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility: Dioxane (Sparingly), DMSO, Methanol (Sparingly)
• PKA: 3.77±0.20(Predicted)
• CAS DataBase Reference: 6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID(81409-74-7)
• EPA Substance Registry System: 6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID(81409-74-7)

Safety Data

• Hazardous Substances Data: 81409-74-7(Hazardous Substances Data)

Usage

Uses

6-Allyl-8β-carboxyergoline is a metabolite of cabergoline (C050000) which is a dopamine D2-receptor agonist.

InChI:InChI=1/C18H20N2O2/c1-2-6-20-10-12(18(21)22)7-14-13-4-3-5-15-17(13)11(9-19-15)8-16(14)20/h2-5,9,12,14,16,19H,1,6-8,10H2,(H,21,22)/t12-,14-,16-/m1/s1

Upstream product

• 5878-43-3 9,10-dihydrolysergic acid 
• 25447-66-9 Dihydroergocryptine 
• 30341-92-5 methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate 
• 80993-64-2 9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate 
• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 81409-91-8 N-<<<3-(dimethylamino)propyl>amino>carbonyl>-N-ethyl-6-(2-propenyl)-ergoline-8β-carboxamide 
• 72821-79-5 methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate 
• 81409-90-7 cabergoline 

Downstream Products

• 81409-86-1 N-cyclohexyl-N-<(cyclohexylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide 
• 81409-90-7 cabergoline 
• 81409-91-8 N-<<<3-(dimethylamino)propyl>amino>carbonyl>-N-ethyl-6-(2-propenyl)-ergoline-8β-carboxamide 
• 85329-88-0 N-methyl-N-<(methylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide 

Relevant articles and documents

Synthesis of novel analogs of cabergoline: Improving cardiovascular safety by removing 5-HT2B receptor agonism

The dopamine agonist cabergoline has been used to treat prolactinomas, Parkinson's disease, Cushing's disease, and sexual dysfunction. However, its clinical use was severely curtailed when it was found that patients taking cabergoline had an increased risk of developing cardiac-valve regurgitation. This potentially life-threatening condition has been associated with drugs, such as cabergoline, that are 5-HT2B receptor agonists. We prepared analogs of cabergoline and have identified several that have limited or no agonism at the 5-HT2B receptor.

New and efficient process for the preperation of cabergoline and its intermediates

This invention relates to a new and efficient process for the production of dopamine agonists such as Cabergoline and the intermediates thereof.