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

• ChemBase ID: 172243
• Molecular Formular: C21H27NO4
• Molecular Mass: 357.44338
• Monoisotopic Mass: 357.19400835
• SMILES: c1(c(cc2c(c1)[C@@H](N(CC2)C)Cc1cc(c(cc1)OC)OC)OC)OC
• Canonical SMILES: COc1cc(ccc1OC)C[C@@H]1N(C)CCc2c1cc(OC)c(c2)OC
• InChI: InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1
• InChIKey: KGPAYJZAMGEDIQ-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• IUPAC Traditional name: laudanosine
• Synonyms: (+)-Laudanosine; (S)-(+)-Laudanosine; (S)-Laudanosine; L-(+)-Laudanosine; L-Laudanosine; (+)-Laudanosine,; NSC 35045; O-Methylcodamine; (S)-Laudanosine; (1S)-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isoquinoline; Laudanosine

Database IDs

• CAS Number: 2688-77-9
• PubChem SID: 164228153
• PubChem CID: 73397

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.6907981
• LogD (pH = 7.4): 2.4632142
• Log P: 3.3967474
• Molar Refractivity: 102.8009 cm^3
• Polarizability: 39.838406 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Classification: Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - L178525

Laudanosine is a metabolite of the neuromuscular-blocking drugs Atracurium (A794500) and Cisatracurium (C496700) with potentially toxic systemic effects. It crosses the blood-brain barrier and may cause excitement and seizure activity.

REFERENCES

• Canfell, P., et al.: Drug Metab. Dispos., 14, 703 (1986)
• Anselmi, E., et al.: J. Pharm. Pharmacol., 44, 337 (1986)
• Bohrer, H., et al.: Pharmacol. Toxicol., 73, 137 (1986)