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

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

Used in Pharmaceutical Industry:
6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID is used as an active pharmaceutical ingredient for the development of medications targeting dopamine D2-receptor agonism. Its application is primarily for the treatment of conditions such as Parkinson's disease, hyperprolactinemia, and certain pituitary tumors, where modulation of dopamine receptors can provide therapeutic benefits.
Used in Research Applications:
In the field of scientific research, 6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID serves as a valuable compound for studying the mechanisms of dopamine receptor interactions and their implications in neurological and endocrine disorders. This research can contribute to the development of novel therapeutic strategies and a better understanding of the underlying biology of related diseases.
Used in Drug Metabolism Studies:
6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID is utilized in drug metabolism studies to understand the biotransformation pathways of cabergoline and related compounds. This knowledge is crucial for assessing the safety, efficacy, and pharmacokinetics of these medications, ensuring optimal dosing regimens and minimizing potential side effects.

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

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

Downstream Products

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

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.