1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

• ChemBase ID: 175671
• Molecular Formular: C20H25NO4
• Molecular Mass: 343.4168
• Monoisotopic Mass: 343.17835829
• SMILES: c1(cc2c(cc1OC)C(NCC2)Cc1ccc(c(c1)OC)OC)OC
• Canonical SMILES: COc1cc(ccc1OC)CC1NCCc2c1cc(OC)c(c2)OC
• InChI: InChI=1S/C20H25NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-6,10-12,16,21H,7-9H2,1-4H3
• InChIKey: YXWQTVWJNHKSCC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• IUPAC Traditional name: 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline; 1,2,3,4-Tetrahydro-6,7-dimethoxy-1-veratrylisoquinoline; (±)-N-Norlaudanosine; (±)-Norlaudanosine; (±)-Tetrahydropapaverine; 1,2,3,4-Tetrahydropapaverine; 1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; Tetrahydropapaverine; rac-Nor Laudanosine

Database IDs

• CAS Number: 13074-31-2
• PubChem SID: 164231581
• PubChem CID: 5418

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.11081835
• LogD (pH = 7.4): 1.1754836
• Log P: 3.0136995
• Molar Refractivity: 97.5062 cm^3
• Polarizability: 37.99663 Å^3
• Polar Surface Area: 48.95 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N710040

Norlaudanosine or Tetrahydroisoquinoline (THIQ) alkaloid is a tumor multi-drug resistance reversing agent.

REFERENCES

• Krishna, R., et al.: Eur. J. Pharm. Sci., 11, 265 (2000)
• Moharram, S., et al.: J. Med. Chem., 47, 1840 (2000)
• Li, Y., et al.: Bioorg. Med. Chem. Lett., 18, 3652 (2000)