5-{[(2H5)phenylcarbamoyl]azanidyl}-3-(1-phenylpropan-2-yl)-1,2,3-oxadiazol-3-ium

• ChemBase ID: 172691
• Molecular Formular: C18H18N4O2
• Molecular Mass: 322.36112
• Monoisotopic Mass: 322.14297584
• SMILES: c1cccc(c1)CC([n+]1noc(c1)[N-]C(=O)Nc1ccccc1)C
• Canonical SMILES: O=C([N-]c1on[n+](c1)C(Cc1ccccc1)C)Nc1ccccc1
• InChI: InChI=1S/C18H18N4O2/c1-14(12-15-8-4-2-5-9-15)22-13-17(24-21-22)20-18(23)19-16-10-6-3-7-11-16/h2-11,13-14H,12H2,1H3,(H-,19,20,21,23)
• InChIKey: OWFUPROYPKGHMH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[(^2H₅)phenylcarbamoyl]azanidyl}-3-(1-phenylpropan-2-yl)-1,2,3-oxadiazol-3-ium
• IUPAC Traditional name: 5-{[(^2H₅)phenylcarbamoyl]azanidyl}-3-(1-phenylpropan-2-yl)-1,2,3-oxadiazol-3-ium
• Synonyms: 3-(1-Methyl-2-phenylethyl)-5-[[[(phenyl-d5)amino]carbonyl]amino]-1,2,3-oxadiazolium Inner Salt; 3-(1-methyl-2-phenylethyl)-N-[[(phenyl-d5)amino]carbonyl]sydnone Imine; 3-(α-Methylphenethyl)-N-[(phenyl-d5)carbamoyl]sydnone Imine; Pharmaneocarb-d5; N-(Phenyl-d5)carbamoyl-3-(β-phenylisopropyl)sydnonimine; Sidnocarb-d5; Sydnocarb-d5; Sydnocarbum-d5; Mesocarb-d5

Database IDs

• PubChem SID: 164228601
• PubChem CID: 71749969

CALCULATED PROPERTIES

• Acid pKa: 7.840893
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.1154312
• LogD (pH = 7.4): 0.9914614
• Log P: 1.1172999
• Molar Refractivity: 112.2656 cm^3
• Polarizability: 34.16941 Å^3
• Polar Surface Area: 68.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225652

Labelled Mesocarb, a CNS stimulant that acts as a dopamine reuptake inhibitor. Mesocarb is a psychotropic drug. Mesocarb is used to counteract the sedative effects of benzodiazepine drugs.

REFERENCES

• Gainetdinov, R.R. et al.: Eur. J. Pharmacol., 340, 53 (1997)
• Kholodov, L.E. et al.: Khim.-Farmat. Zhur., 7, 50 (1997)
• Valueva, L.N. et al.: Zhur. Nevropatol. Psikh. S. S. Korsak., 82, 1212 (1997)