(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol hydrochloride

• ChemBase ID: 177429
• Molecular Formular: C19H24ClNO4
• Molecular Mass: 365.85116
• Monoisotopic Mass: 365.13938593
• SMILES: c1(c(cc2c(c1)[C@@H](N(CC2)C)Cc1cc(c(cc1)OC)O)OC)O.Cl
• Canonical SMILES: COc1ccc(cc1O)C[C@@H]1N(C)CCc2c1cc(O)c(c2)OC.Cl
• InChI: InChI=1S/C19H23NO4.ClH/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;/h4-5,9-11,15,21-22H,6-8H2,1-3H3;1H/t15-;/m0./s1
• InChIKey: BLFMXKJHMQFPFA-RSAXXLAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol hydrochloride
• IUPAC Traditional name: (+)-reticuline hydrochloride
• Synonyms: (1S)-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol Hydrochloride; (+)-Reticuline Hydrochloride; L-(+)-Reticuline Hydrochloride; Reticulin Hydrochloride; S-(+)-Reticuline Hydrochloride; d-Reticuline Hydrochloride; Reticuline Hydrochloride Salt (>90% ee)

Database IDs

• CAS Number: 903-91-3
• PubChem SID: 164233339
• PubChem CID: 71752016

CALCULATED PROPERTIES

• Acid pKa: 9.764061
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.7340227
• LogD (pH = 7.4): 2.4816308
• Log P: 3.1049592
• Molar Refractivity: 93.8363 cm^3
• Polarizability: 36.01199 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 125-126°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R188500

Precursor of many aporphine and morphine-type alkaloids.

REFERENCES

• Kutchan, T., et al.: J. Biol. Chem., 270, 24475 (1995)
• Winkler, A., et al.: J. Biol. Chem., 282, 24437 (1995)
• Heuts, D., et al.: Biochem. J., 413, 175 (1995)