Pharmakon1600-00300565

Base Information

• Chemical Name: Pharmakon1600-00300565
• CAS No.: 17692-51-2
• Molecular Formula: C25H29N3O2
• Molecular Weight: 403.524
• NSC Number: 755878
• ChEMBL ID: CHEMBL1526242
• Mol file: 17692-51-2.mol

Synonyms:Spectrum_000006;Spectrum2_000882;Spectrum3_001254;Spectrum4_000105;Spectrum5_000926;BSPBio_002788;KBioGR_000430;KBioSS_000346;SPECTRUM300565;DivK1c_000266;SPBio_000664;CHEMBL1526242;HMS500N08;KBio1_000266;KBio2_000346;KBio2_002914;KBio2_005482;KBio3_002288;NINDS_000266;HMS1923G17;Pharmakon1600-00300565;NSC755878;CCG-213740;IDI1_000266;NCGC00017257-04;NCGC00095251-01;NCGC00095251-02;NCGC00095251-03;SBI-0051256.P002;AB00051894_02;BRD-A72309220-001-03-3

Chemical Property of Pharmakon1600-00300565

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 148-150 °C(lit.)
• Boiling Point: 612.5 °C at 760 mmHg
• PKA: 12.45±0.46(Predicted)
• Flash Point: 324.2 °C
• PSA: 46.50000
• Density: 1.25 g/cm³
• LogP: 4.39350
• Storage Temp.: −20°C
• Solubility.: 0.1 M HCl: 1.4 mg/mL
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 403.22597718
• Heavy Atom Count: 30
• Complexity: 607

Purity/Quality:

99% ^*data from raw suppliers

Metergoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CC(CC2C1CC3=CN(C4=CC=CC2=C34)C)CNC(=O)OCC5=CC=CC=C5
• Isomeric SMILES: CN1CC(C[C@@H]2C1CC3=CN(C4=CC=CC2=C34)C)CNC(=O)OCC5=CC=CC=C5
• Description: Metergoline (17692-51-2) is an ergot alkaloid derivative acting as antagonist at serotonin 5HT1 and 5HT2 receptors1,2 and 5HT7 receptors3. A safe and effective agent for management of hyperprolactinemic amenorrhea and anovulation.4 Displays a long-lasting antidepressant effect in seasonal affective disorder.5
• Uses: Metergoline is an antagonist at 5-HT1, 5-HT2, and 5-HT7 serotonin receptors. Metergoline is an analgesic; antipyretic.
• Therapeutic Function: Analgesic

Technology Process of Pharmakon1600-00300565

There total 1 articles about Pharmakon1600-00300565 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:

→ Metergoline (17692-51-2)

Guidance literature:

PhCH2O-CO-Cl, entspr. Amin;

Reference yield: 57.0%

N-acetyl-N-methyl-O-2,4-dinitrophenylhydroxylamine (38100-40-2) + metergoline (17692-51-2) → benzyl (((6aR,9S,10aR)-4,7-dimethyl-5-(N-methylacetamido)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl)carbamate

Guidance literature:

With potassium carbonate; eosin y; In acetone; at 20 ℃; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1021/jacs.6b04920

Reference yield:

metergoline (17692-51-2) → N-(((6aR,9S,10aR)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl)propionamide (2169-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol; water / 16 h / 20 °C

2: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 24 h / 20 °C

With palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water;

DOI:10.1039/c3md00310h

Downstream raw materials:

N-(((6aR,9S,10aR)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl)propionamide