3-(2-iodobenzoyl)-1-[(1-methylpiperidin-2-yl)methyl]-1H-indole

• ChemBase ID: 125769
• Molecular Formular: C22H23IN2O
• Molecular Mass: 458.33529
• Monoisotopic Mass: 458.08551137
• SMILES: Ic1ccccc1C(=O)c1cn(CC2CCCCN2C)c2c1cccc2
• 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-methylpiperidin-2-yl)methyl]-1H-indole
• IUPAC Traditional name: 3-(2-iodobenzoyl)-1-[(1-methylpiperidin-2-yl)methyl]indole
• Synonyms: AM-2233; (2-Iodophenyl)[1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl]methanone; 1-[(N-Methyl-2-piperidinyl)methyl]-3-(2-iodobenzoyl)-1H-indole; (2-Iodophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)methanone

Database IDs

• CAS Number: 444912-75-8
• MDL Number: MFCD21603816
• PubChem SID: 162220116
• PubChem CID: 10226340
• CHEMBL: 364266
• Chemspider ID: 8401830
• Wikipedia Title: AM-2233

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: 45.704346 Å^3
• Polar Surface Area: 25.24 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: WHite Solid
• Melting Point: 144-146°C

Safety Information

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

Pharmacology Properties

• Legal Status: Temporary Class Drug (NZ)

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - 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)-enantiomer.

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)