4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(2H3)methoxybenzamide

• ChemBase ID: 174576
• Molecular Formular: C14H22ClN3O2
• Molecular Mass: 299.79638
• Monoisotopic Mass: 299.14005464
• SMILES: c1(c(cc(c(c1)C(=O)NCCN(CC)CC)OC)N)Cl
• Canonical SMILES: CCN(CCNC(=O)c1cc(Cl)c(cc1OC)N)CC
• InChI: InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
• InChIKey: TTWJBBZEZQICBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(^2H₃)methoxybenzamide
• IUPAC Traditional name: 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(^2H₃)methoxybenzamide
• Synonyms: 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(methoxy-d3)benzamide; 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-o-anisamide-d3; 2-(Methoxy-d3)-5-chloroprocainamide; Clopromate-d3; DEL 1267-d3; Draclamid-d3; Emperal-d3; Eucil-d3; Gastrese-d3; Gastrobid-d3; Gastromax-d3; Gastrosil-d3; Gastrotem-d3; Maxeran-d3; Meclopran-d3; Metamide-d3; Reliveran-d3; Metoclopramide-d3

Database IDs

• PubChem SID: 164230486
• PubChem CID: 12598248

CALCULATED PROPERTIES

• Acid pKa: 14.490737
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.8242222
• LogD (pH = 7.4): -0.2508232
• Log P: 1.3972701
• Molar Refractivity: 83.5178 cm^3
• Polarizability: 31.28165 Å^3
• Polar Surface Area: 67.59 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 143-148°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M338687

Labelled dopamine D2 receptor antagonist. A labelled substituted benzamide with neuroleptic activity. Antiemetic.

REFERENCES

• Kebabian, J.W., et al.: Nature, 277, 93 (1979)
• Pakula, R., et al.: Arch. Pharm., 313, 297 (1979)
• Vergin, H., et al.: Arzneim.-Forsch., 33, 458 (1979)
• Pitre, D., et al.: anal. Profiles Drug Subs., 16, 327 (1979)