7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydroisoquinolin-2-ium iodide

• ChemBase ID: 165690
• Molecular Formular: C19H22INO4
• Molecular Mass: 455.28675
• Monoisotopic Mass: 455.05935619
• SMILES: c1(c(cc2c(c1)C(=[N+](CC2)C)Cc1cc(c(cc1)OC)O)OC)O.[I-]
• Canonical SMILES: COc1ccc(cc1O)CC1=[N+](C)CCc2c1cc(O)c(c2)OC.[I-]
• InChI: InChI=1S/C19H21NO4.HI/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12;/h4-5,9-11H,6-8H2,1-3H3,(H-,21,22);1H
• InChIKey: UKZNQWRHVOGFFY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydroisoquinolin-2-ium iodide
• IUPAC Traditional name: 1,2-dehydroreticuline iodide
• Synonyms: 3,4-Dihydro-7-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methylisoquinolinium Iodide; 1,2-Dehydroreticuline Iodide; 3,4-Dihydro-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolinium Iodide; 1,2-Dehydro Reticuline Iodide

Database IDs

• CAS Number: 21411-21-2
• PubChem SID: 162259823
• PubChem CID: 71315340

CALCULATED PROPERTIES

• Acid pKa: 9.4563265
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.791093
• LogD (pH = 7.4): -0.46167868
• Log P: -0.79748017
• Molar Refractivity: 104.4459 cm^3
• Polarizability: 35.561638 Å^3
• Polar Surface Area: 61.93 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230065

1,2-Dehydro Reticuline Iodide is a dehydro iminium salt derivative of Reticuline (R188500) and a precursor in the synthesis of Multifloramine.

REFERENCES

• He, X. et al.: J. Nat. Prod., 56, 973 (1993)
• Teitel, S. et al.: J. Heterocyc. Chem., 5, 825 (1993)