N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Base Information

• Chemical Name: N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• CAS No.: 81409-90-7
• Molecular Formula: C26H37N5O2
• Molecular Weight: 451.612
• Hs Code.: 2939690000
• European Community (EC) Number: 627-031-8
• DSSTox Substance ID: DTXSID20861039
• Wikidata: Q27163596
• ChEMBL ID: CHEMBL1898147
• Mol file: 81409-90-7.mol

Synonyms:Cabergoline-d5;N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;1426173-20-7;NCGC00167821-01;CHEMBL1898147;BDBM86052;CHEBI:91795;DTXSID20861039;HMS3269L07;(6aR,9R,10aR)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;CAS_54746;NSC_54746;L000974;BRD-A63043573-001-01-6;Q27163596;N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-(prop-2-en-1-yl)ergoline-8-carboxamide

Chemical Property of N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Chemical Property:

• Appearance/Colour: White crystalline solid
• Melting Point: 102-104°C
• Refractive Index: 1.594
• PKA: 13.05±0.46(Predicted)
• PSA: 71.68000
• Density: 1.156 g/cm³
• LogP: 3.52270
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 451.29472544
• Heavy Atom Count: 33
• Complexity: 713

Purity/Quality:

98% ^*data from raw suppliers

Cabergoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC(=O)N(CCCN(C)C)C(=O)C1CC2C(CC3=CNC4=CC=CC2=C34)N(C1)CC=C
• Description: Cabergoline is a potent, selective, and long-lasting dopamine D2 receptor agonist launched in 1993 in Belgium as a prolactin inhibitor. A single 1 mg dose of cabergoline effectively prevents puerperal lactation for up to 14 days, remarkably superior to other drugs that require a daily regimen. It has a low rate of rebound breast activity and good tolerability. Cabergoline is also in clinical trials for Parkinson's disease, breast cancer, and hyperprolactinaemia.
• Uses: A dopamine D2-receptor agonist. receptor stimulant Cabergoline is an ergot derivative and a dopamine D2-receptor agonist (1,2,3). It inhibits the secretion of prolactin and growth hormone.
• Clinical Use: Endocrine disorders Adjunct to levodopa (with a decarboxylase inhibitor) in Parkinson’s disease Inhibition / suppression of lactation
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

There total 19 articles about N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.3%

6-Norcabergoline (153415-36-2) + Allyl acetate (591-87-7) → cabergoline (81409-90-7,856676-33-0)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 20 ℃; for 2h;

Reference yield: 90.0%

1-((6-allylergolin-8β-yl)-carbonyl)-1-(3-dimethylaminopropyl)-3-ethylurea chlorobenzene solvate → cabergoline (81409-90-7,856676-33-0)

Guidance literature:

In n-heptane; at 55 ℃; Product distribution / selectivity;

Reference yield: 86.0%

Cabergoline ethylbenzene/n-heptane → cabergoline (81409-90-7,856676-33-0)

Guidance literature:

for 15h; Product distribution / selectivity; Drying under a blanket of nitrogen;

upstream raw materials:

1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

ethyl isocyanate

Downstream raw materials:

C₂₇H₃₆F₃N₅O₂

(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AMORPHOUS CABERGOLINE". Page/Page column 4,5. . Retrieved 2008/12/07.
• 2、 -. "New crystal form of cabergoline". Page/Page column 7. . Retrieved 2008/12/07.