2-(dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate

• ChemBase ID: 124981
• Molecular Formular: C22H29NO5
• Molecular Mass: 387.46936
• Monoisotopic Mass: 387.20457303
• SMILES: c1(c(cc(C(=O)OCC(N(C)C)(c2ccccc2)CC)cc1OC)OC)OC
• Canonical SMILES: CCC(c1ccccc1)(N(C)C)COC(=O)c1cc(OC)c(c(c1)OC)OC
• InChI: InChI=1S/C22H29NO5/c1-7-22(23(2)3,17-11-9-8-10-12-17)15-28-21(24)16-13-18(25-4)20(27-6)19(14-16)26-5/h8-14H,7,15H2,1-6H3
• InChIKey: LORDFXWUHHSAQU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate
• IUPAC Traditional name: trimebutine; 2-(dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate
• Synonyms: 3,4,5-Trimethoxybenzoic acid 2-(dimethylamino)-2-phenylbutyl ester; Trimebutine; 2-(dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate; Trimebutine; Cerekinon; Digerent; Mebutin; Spabucol; 3,4,5-三甲氧基苯甲酸 2-(二甲氨基)-2-苯基丁酯; 曲美布汀

Database IDs

• CAS Number: 39133-31-8
• EC Number: 254-309-2
• MDL Number: MFCD00133873
• PubChem SID: 162219334; 24900356
• PubChem CID: 5573

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.0457101
• LogD (pH = 7.4): 2.733307
• Log P: 4.1096926
• Molar Refractivity: 108.937 cm^3
• Polarizability: 42.628212 Å^3
• Polar Surface Area: 57.23 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• 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

• Target: Opioid Receptor
• Mechanism of Action: (i) an agonist effect on peripheral mu, kappa and delta opiate receptors and; (ii) release of gastrointestinal peptides such as motilin and modulation of the release of other peptides, including vasoactive intestinal peptide, gastrin and glucagon; The actions of trimebutine on the gastrointestinal tract are mediated via

Product Information

• Grade: analytical standard
• Salt Data: Free Base
• Application(s): Antispasmodic agent
• Empirical Formula (Hill Notation): C22H29NO5

REFERENCES

• U.K. Pat., 1972, 1 342 547; CA, 78, 58079j, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6665
• Fraitag, B. et al., Gastroenterol. Clin. Biol., 1992, 16, 413, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1423
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TKU650; TKU675