(1R)-1-{[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

• ChemBase ID: 126468
• Molecular Formular: C28H38N2O4
• Molecular Mass: 466.61232
• Monoisotopic Mass: 466.28315771
• SMILES: Oc1cc2c(cc1OC)[C@H](NCC2)C[C@H]1C[C@H]2c3c(cc(OC)c(OC)c3)CCN2C[C@@H]1CC
• Canonical SMILES: CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1C[C@H]1NCCc2c1cc(OC)c(c2)O)cc(c(c3)OC)OC
• InChI: InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23+,24-/m0/s1
• InChIKey: DTGZHCFJNDAHEN-OZEXIGSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-{[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
• IUPAC Traditional name: cephaeline
• Synonyms: (1R)-1-[[(2S,3R,11bS)-3-Ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizin-2-yl]methyl]-1,2,3,4-tetrahydro-7-methoxy-6-isoquinolinol; 7',10,11-Trimethoxyemetan-6'-ol; (-)-Cephaeline; 4-[[4-[(Aminoiminomethyl)amino]benzoyl]oxy]benzeneacetic Acid 2-(Dimethylamino)-2-oxoethyl Ester Methanesulfonate; FOY 305; FOY-S 980; Foipan; Camostat Mesylate; Cepheline; Desmethylemetine; Dihydropsychotrine; Cephaeline

Database IDs

• CAS Number: 59721-29-8; 483-17-0; 483-18-1
• PubChem SID: 162220802
• PubChem CID: 442195
• CHEMBL: 255708
• Chemspider ID: 390702
• Unique Ingredient Identifier: QA971541A1
• Wikipedia Title: Cephaeline

CALCULATED PROPERTIES

• Acid pKa: 10.146319
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.2912607
• LogD (pH = 7.4): 1.6733295
• Log P: 3.9145982
• Molar Refractivity: 135.2684 cm^3
• Polarizability: 52.72534 Å^3
• Polar Surface Area: 63.19 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; soluble in alcohol
• Apperance: Off-White to Pale Yellow Solid; white silky crystals; White Solid
• Melting Point: 162-164°C; 98-100°C

Safety Information

• Storage Condition: -20°C Freezer; Refrigerator
• Main Hazard: emetic / poisonous

DETAILS

Toronto Research Chemicals - C256700

Has been used as an emetic and expectorant.

Toronto Research Chemicals - C150300

Orally active, non-peptide proteolitic enzyme inhibitor with anti-trypsin and anti-plasmin activities, related structurally to gabexate. Protease inhibitor.

REFERENCES

• Crouch, D.J., et al.: J. Anal. Toxicol., 8, 63 (1984)
• Guengerich, F., et al.: Pharmacol. Ther., 54, 17 (1984)
• Myers, C., et al.: Environ. Toxicol. Chem., 13, 461 (1984)
• Tamura, Y., et al.: Biochem. Biophys. Acta, 484, 417 (1977)
• Takasugi, S., et al.: Digestion, 24, 36 (1977)