(9R)-4-methoxy-10-(2H3)methyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,13,15-hexaen-3-ol hydrochloride

• ChemBase ID: 160757
• Molecular Formular: C18H20ClNO2
• Molecular Mass: 317.8099
• Monoisotopic Mass: 317.11825657
• SMILES: c1(ccc2c(c1O)c1c3[C@@H](C2)N(CCc3ccc1)C)OC.Cl
• Canonical SMILES: COc1ccc2c(c1O)c1cccc3c1[C@@H](C2)N(C)CC3.Cl
• InChI: InChI=1S/C18H19NO2.ClH/c1-19-9-8-11-4-3-5-13-16(11)14(19)10-12-6-7-15(21-2)18(20)17(12)13;/h3-7,14,20H,8-10H2,1-2H3;1H/t14-;/m1./s1
• InChIKey: NIWCFXFECXNXGD-PFEQFJNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9R)-4-methoxy-10-(^2H₃)methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaen-3-ol hydrochloride
• IUPAC Traditional name: (9R)-4-methoxy-10-(^2H₃)methyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,13,15-hexaen-3-ol hydrochloride
• Synonyms: 6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-(methyl-d3)-4H-dibenzo[de,g]quinolin-11-ol Hydrochloride; 10-Methoxy-6aβ-aporphin-11-ol-d3 Monohydrochloride; NSC 305238-d3; (R-(-)-Apocodeine-d3 Hydrochloride

Database IDs

• PubChem SID: 162254892
• PubChem CID: 71313463

CALCULATED PROPERTIES

• Acid pKa: 9.735198
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.95085394
• LogD (pH = 7.4): 2.6807487
• Log P: 3.1331258
• Molar Refractivity: 84.4704 cm^3
• Polarizability: 33.559685 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A727102

A labelled metabolite of Apomorphine (A727500). Dopamine receptor agonist. Emetic.

REFERENCES

• Neumeyer, et al.: J. Med. Chem., 16, 1223 (1973)
• Fong, T., et al.: Cancer Res., 59, 99 (1973)
• Hayashi, Y., et al.: J. Biol. Chem., 278, 25166 (1973)
• O'Neill, J., et al.: Science, 320, 949 (1973)