(6aR,10aR)-6,6,9-trimethyl-3-[(2,2,3,3,4,4,5,5,5-2H9)pentyl]-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

• ChemBase ID: 178291
• Molecular Formular: C21H30O2
• Molecular Mass: 314.4617
• Monoisotopic Mass: 314.2245802
• SMILES: C1(=C[C@@H]2[C@@H](CC1)C(Oc1c2c(cc(c1)CCCCC)O)(C)C)C
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(C)CC1)(C)C
• InChI: InChI=1S/C21H30O2/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/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
• InChIKey: CYQFCXCEBYINGO-IAGOWNOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,10aR)-6,6,9-trimethyl-3-[(2,2,3,3,4,4,5,5,5-^2H₉)pentyl]-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
• IUPAC Traditional name: (6aR,10aR)-6,6,9-trimethyl-3-[(2,2,3,3,4,4,5,5,5-^2H₉)pentyl]-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
• Synonyms: (6aR,10aR)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol-d9; Δ9-trans-Tetrahydrocannabinol-d9; Abbott 40566-d9; Dronabinol-d9; Marinol-d9; NSC 134454-d9; QCD 84924-d9; SP 104-d9; THC-d9; Δ9-Tetrahydro Cannabinol-d9

Database IDs

• PubChem SID: 164234201
• PubChem CID: 46783039

CALCULATED PROPERTIES

• Acid pKa: 9.342429
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.944095
• LogD (pH = 7.4): 5.9392576
• Log P: 5.944157
• Molar Refractivity: 96.7335 cm^3
• Polarizability: 37.476387 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Light Yellow Oil

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - T293202

It is the principal active constituent of cannabis. Agonist at CB1 and CB2 cannabinoid receptors. Antiemetic; appetite stimulant. Controlled substance (hallucinogen).

REFERENCES

• Rosenkranz, H., et al.: Toxicol., 1416, 2111 (1967)
• Tanda, G., et al.: Eur. J. Pharmacol., 376, 23 (1967)
• Dewey, W.L., et al.: Pharmacol. Rev., 38, 151 (1967)
• Grotenhermen, F., et al.: Clin. Pharmacokinet., 42, 327 (1967)