(6aS,10aR)-1-hydroxy-6,6-bis(2H3)methyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one

• ChemBase ID: 174893
• Molecular Formular: C24H36O3
• Molecular Mass: 372.54084
• Monoisotopic Mass: 372.26644501
• SMILES: C1(=O)CC[C@H]2[C@@H](C1)c1c(OC2(C)C)cc(cc1O)C(CCCCCC)(C)C
• Canonical SMILES: CCCCCCC(c1cc(O)c2c(c1)OC([C@@H]1[C@H]2CC(=O)CC1)(C)C)(C)C
• InChI: InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19+/m1/s1
• InChIKey: GECBBEABIDMGGL-MOPGFXCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aS,10aR)-1-hydroxy-6,6-bis(^2H₃)methyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one
• IUPAC Traditional name: (6aS,10aR)-1-hydroxy-6,6-bis(^2H₃)methyl-3-(2-methyloctan-2-yl)-6aH,7H,8H,10H,10aH-benzo[c]isochromen-9-one
• Synonyms: (6aR,10aS)-rel-3-(1,1-Dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one-d6; cis-(+/-)-3-(1,1-Dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one-d6; cis-Nabilone-d6

Database IDs

• PubChem SID: 164230803
• PubChem CID: 71750881

CALCULATED PROPERTIES

• Acid pKa: 9.328193
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 6.359639
• LogD (pH = 7.4): 6.3546414
• Log P: 6.3597035
• Molar Refractivity: 110.202 cm^3
• Polarizability: 43.29592 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - N199992

An inactive isomer of Nabilone, present often as an impurity in labelled trans-Nabilone preparations.

REFERENCES

• Rubin, A., et al.: Clin. Pharmacol. Ther., 22, 85 (1977)
• Stark, P., et al.: J. Pharmacol. Exp. Ther., 214, 124 (1977)
• Souter, R.W., et al.: Anal. Profiles Drug Subs., 10, 499 (1977)
• Ward, A., Drugs, 30, 127 (1977)