3-(2-iodobenzoyl)-1-{[1-(2H3)methylpiperidin-2-yl](2H2)methyl}-1H-indole

• ChemBase ID: 159761
• Molecular Formular: C22H23IN2O
• Molecular Mass: 458.33529
• Monoisotopic Mass: 458.08551137
• SMILES: c1ccc2c(c1)c(cn2CC1N(CCCC1)C)C(=O)c1ccccc1I
• Canonical SMILES: CN1CCCCC1Cn1cc(c2c1cccc2)C(=O)c1ccccc1I
• InChI: InChI=1S/C22H23IN2O/c1-24-13-7-6-8-16(24)14-25-15-19(17-9-3-5-12-21(17)25)22(26)18-10-2-4-11-20(18)23/h2-5,9-12,15-16H,6-8,13-14H2,1H3
• InChIKey: KSLCYQTUSSEGPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-iodobenzoyl)-1-{[1-(^2H₃)methylpiperidin-2-yl](^2H₂)methyl}-1H-indole
• IUPAC Traditional name: 3-(2-iodobenzoyl)-1-{[1-(^2H₃)methylpiperidin-2-yl](^2H₂)methyl}indole
• Synonyms: 1-[(N-Methyl-2-piperidinyl)methyl]-3-(2-iodobenzoyl)-1H-indole-d5; AM-2233-d5; (2-Iodophenyl)[1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl]methanone-d5

Database IDs

• PubChem SID: 162253896
• PubChem CID: 71313128

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.6296546
• LogD (pH = 7.4): 4.351269
• Log P: 5.612759
• Molar Refractivity: 115.8105 cm^3
• Polarizability: 45.783543 Å^3
• Polar Surface Area: 25.24 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 146-148°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A575852

Labelled AM-2233 (A575850). A potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor. (AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enan

REFERENCES

• Neumeyer, J., et al.: J. Med. Chem., 33, 521 (1990)
• D'Ambra, T., et al.: Bioorg. Med. Chem. Lett., 6, 17 (1990)
• Schatz, A., et al.: Toxicol. Appl. Pharmacol., 142, 278 (1990)