1-butyl-N-(2,4,6-trimethylphenyl)pyrrolidine-2-carboxamide

• ChemBase ID: 179778
• Molecular Formular: C18H28N2O
• Molecular Mass: 288.42772
• Monoisotopic Mass: 288.22016353
• SMILES: C(=O)(Nc1c(cc(cc1C)C)C)C1N(CCC1)CCCC
• Canonical SMILES: CCCCN1CCCC1C(=O)Nc1c(C)cc(cc1C)C
• InChI: InChI=1S/C18H28N2O/c1-5-6-9-20-10-7-8-16(20)18(21)19-17-14(3)11-13(2)12-15(17)4/h11-12,16H,5-10H2,1-4H3,(H,19,21)
• InChIKey: VEPZOLKTNZOTTQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-butyl-N-(2,4,6-trimethylphenyl)pyrrolidine-2-carboxamide
• IUPAC Traditional name: 1-butyl-N-(2,4,6-trimethylphenyl)pyrrolidine-2-carboxamide
• Synonyms: 1-Butyl- N -(2,4,6-trimethylphenyl)-2-pyrrolidinecarboxamide; 1-Butyl-2',4',6'-trimethyl-2-pyrrolidinecarboxanilide; Bumecaine

Database IDs

• CAS Number: 30103-44-7
• PubChem SID: 164235688
• PubChem CID: 65770

CALCULATED PROPERTIES

• Acid pKa: 13.988217
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.9870455
• LogD (pH = 7.4): 3.7605956
• Log P: 4.5843716
• Molar Refractivity: 90.6335 cm^3
• Polarizability: 34.206745 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Potassium channel (K ATP and K Vol ) blocker

Product Information

• Application(s): Antiarrhythmic agent; Local anaesthetic

REFERENCES

• Likhosherstov, A.M. et al., Khim.-Farm. Zh., 1970, 4, 27, (synth)
• Pryanishnikova, N.T. et al., Khim.-Farm. Zh., 1971, 5, 7; 1975, 9, 59, (synth, pharmacol, tox)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PQB750