5,7,17,19-tetraoxa-13λ5-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaen-13-ylium chloride

• ChemBase ID: 164960
• Molecular Formular: C19H14ClNO4
• Molecular Mass: 355.77176
• Monoisotopic Mass: 355.06113561
• SMILES: [Cl-].c12c(cc3c(c1)c1[n+](CC3)cc3c(c1)ccc1c3OCO1)OCO2
• Canonical SMILES: C1Oc2c(O1)cc1c(c2)CC[n+]2c1cc1ccc3c(c1c2)OCO3.[Cl-]
• InChI: InChI=1S/C19H14NO4.ClH/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14;/h1-2,5-8H,3-4,9-10H2;1H/q+1;/p-1
• InChIKey: LUXPUVKJHVUJAV-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7,17,19-tetraoxa-13λ^5-azahexacyclo[11.11.0.0^2,^1^0.0^4,^8.0^1^5,^2^3.0^1^6,^2^0]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaen-13-ylium chloride
• IUPAC Traditional name: coptisine chloride
• Synonyms: 6,7-Dihydrobis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium Chloride; 7,8,13,13a-Tetradehydro-2,3:9,10-bis(methylenedioxy)berbinium Chloride; Coptisine Chloride; Coptisine Chloride

Database IDs

• CAS Number: 6020-18-4
• PubChem SID: 162259094
• PubChem CID: 72321

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.3447363
• LogD (pH = 7.4): -1.3447363
• Log P: -1.3447363
• Molar Refractivity: 86.3638 cm^3
• Polarizability: 35.870968 Å^3
• Polar Surface Area: 40.8 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly)
• Apperance: Orange Brown Solid
• Melting Point: >258°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C685500

Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis). A bacterial collagenase inhibitor. Coptisine has been found to reversibly inhibit Monoamine oxidase A in mice, pointing to a potential role as a natural antidepressant.

REFERENCES

• Blaney, W., et al.: Physiol. Entomol., 12, 281 (1987)
• Sethi, M., et al.: J. Pharm. Sci., 72, 538 (1987)
• Yahara, S., et al.: Chem. Pharm. Bull., 33, 527 (1987)