(1R,9R,13R)-10-(cyclopropylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol

• ChemBase ID: 153565
• Molecular Formular: C18H25NO
• Molecular Mass: 271.3972
• Monoisotopic Mass: 271.19361443
• SMILES: C[C@H]1[C@H]2Cc3ccc(cc3[C@@]1(CCN2CC1CC1)C)O
• Canonical SMILES: Oc1ccc2c(c1)[C@]1(C)CCN([C@H](C2)[C@@H]1C)CC1CC1
• InChI: InChI=1S/C18H25NO/c1-12-17-9-14-5-6-15(20)10-16(14)18(12,2)7-8-19(17)11-13-3-4-13/h5-6,10,12-13,17,20H,3-4,7-9,11H2,1-2H3/t12-,17+,18+/m0/s1
• InChIKey: YQYVFVRQLZMJKJ-JBBXEZCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,13R)-10-(cyclopropylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2,4,6-trien-4-ol
• IUPAC Traditional name: (1R,9R,13R)-10-(cyclopropylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2,4,6-trien-4-ol
• Synonyms: (+)-Cyclazocine

Database IDs

• CAS Number: 3572-80-3
• EC Number: 222-689-9
• PubChem SID: 162247704; 24277963
• PubChem CID: 3037926

CALCULATED PROPERTIES

• Acid pKa: 9.936118
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.21794558
• LogD (pH = 7.4): 0.8067302
• Log P: 2.9150462
• Molar Refractivity: 82.6231 cm^3
• Polarizability: 32.232426 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble; 0.1 M NaOH: insoluble; ethanol: soluble; H2O: insoluble
• Apperance: white solid
• Optical Rotation: [α]23/D +119.3°, c = 1.0 in ethanol(lit.)

Safety Information

• RTECS: PB8585000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... OPRK1(4986), OPRS1(10280)rat ... Oprm1(25601)

Product Information

• Empirical Formula (Hill Notation): C18H25NO

DETAILS

Sigma Aldrich - C147

Caution
Photosensitive
Biochem/physiol Actions
σ receptor agonist that is also an agonist at κ opioid receptors and an antagonist at μ opioid receptors.