2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraene; ethene

• ChemBase ID: 179573
• Molecular Formular: C29H30N2O3
• Molecular Mass: 454.5601
• Monoisotopic Mass: 454.22564283
• SMILES: C1COCCN1CC1n2c3c(OC1)cccc3c(c2C)C(=O)c1c2c(ccc1)cccc2.C=C
• Canonical SMILES: O=C(c1c(C)n2c3c1cccc3OCC2CN1CCOCC1)c1cccc2c1cccc2.C=C
• InChI: InChI=1S/C27H26N2O3.C2H4/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28;1-2/h2-11,20H,12-17H2,1H3;1-2H2
• InChIKey: SPAQJJGIWQTTPX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0^4,^1^2]dodeca-2,4,6,8(12)-tetraene; ethene
• IUPAC Traditional name: 2-methyl-11-(morpholin-4-ylmethyl)-3-(naphthalene-1-carbonyl)-9-oxa-1-azatricyclo[6.3.1.0^4,^1^2]dodeca-2,4,6,8(12)-tetraene; ethylene
• Synonyms: [(3R)-2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenylmethanone; (R)-(+)-Win 55212-2; (R)-Win 55212; Win 2; (R)-[2,3-dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenylmethanone; Win 55212-2

Database IDs

• CAS Number: 131543-22-1
• PubChem SID: 164235483
• PubChem CID: 71752994

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.5463715
• LogD (pH = 7.4): 4.4356165
• Log P: 4.47479
• Molar Refractivity: 125.4746 cm^3
• Polarizability: 50.788803 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - W498850

A synthetic CB1/CB2 cannabinoid receptor agonist. It is potent analgesic and has anti-inflammatory properties. It activates p42 and p44 MAP kinase via receptor-mediated signaling.

REFERENCES

• Meng, I.D. et al.: Nature, 395, 381 (1998)
• Bouaboula, M. et al. Biochem. J., 312, 637 (1998)
• Niederhoffer, N. et al.: Br. J. Pharamcol., 126, 457 (1998)
• Marchalant, Y. et al.: Neurosci., 144, 1516 (1998)