6,6,9-trimethyl-3-[(2,2,3,3,4,4,5,5,5-2H9)pentyl]-6H-benzo[c]chromen-1-ol

• ChemBase ID: 163587
• Molecular Formular: C21H26O2
• Molecular Mass: 310.42994
• Monoisotopic Mass: 310.19328007
• SMILES: c1(ccc2c(c1)c1c(OC2(C)C)cc(cc1O)CCCCC)C
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC(c1c2cc(C)cc1)(C)C
• InChI: InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3
• InChIKey: VBGLYOIFKLUMQG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,6,9-trimethyl-3-[(2,2,3,3,4,4,5,5,5-^2H₉)pentyl]-6H-benzo[c]chromen-1-ol
• IUPAC Traditional name: 6,6,9-trimethyl-3-[(2,2,3,3,4,4,5,5,5-^2H₉)pentyl]benzo[c]chromen-1-ol
• Synonyms: 6,6,9-Trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol-d9; 3-Amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-d9; CBN-d9; NSC 134455-d9; Cannabinol-d9

Database IDs

• PubChem SID: 162257722
• PubChem CID: 71314492

CALCULATED PROPERTIES

• Acid pKa: 9.318134
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.4126654
• LogD (pH = 7.4): 6.4075513
• Log P: 6.412731
• Molar Refractivity: 95.7363 cm^3
• Polarizability: 38.325905 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C175352

A labelled metabolite of Tetrahydrocannabinol (T293200). A psychoactive substance cannabinoid that acts as a weak agonist of the CB1 and CB2 receptors.

REFERENCES

• Yamamoto, I. et al.: Chem. Pharmac. Bull., 35, 2144 (1987)
• Hawksworth, G. et al.: Med. Use Cannabis Cannabinoid, 205 (1987)
• Holdcroft, A. et al. Pharmac. Sci., 3, 546 (1987)