[(E)-N-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)carbamimidoyl]urea

• ChemBase ID: 164763
• Molecular Formular: C10H18N6OS
• Molecular Mass: 270.35452
• Monoisotopic Mass: 270.12628023
• SMILES: c1(CSCC/N=C(/NC(=O)N)\NC)c([nH]cn1)C
• Canonical SMILES: CN/C(=N\CCSCc1nc[nH]c1C)/NC(=O)N
• InChI: InChI=1S/C10H18N6OS/c1-7-8(15-6-14-7)5-18-4-3-13-10(12-2)16-9(11)17/h6H,3-5H2,1-2H3,(H,14,15)(H4,11,12,13,16,17)
• InChIKey: GWWANUFLANSTTA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(E)-N-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)carbamimidoyl]urea
• IUPAC Traditional name: (E)-N-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)carbamimidoylurea
• Synonyms: [(Methylamino)[[2-[[5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]amino]methylene]- urea Dihydrochloride; Cimetidine Amide Dihydrochloride

Database IDs

• CAS Number: 52568-80-6
• PubChem SID: 162258898
• PubChem CID: 131743

CALCULATED PROPERTIES

• Acid pKa: 13.078852
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -3.3849726
• LogD (pH = 7.4): -1.158348
• Log P: -0.7695859
• Molar Refractivity: 72.7041 cm^3
• Polarizability: 27.277514 Å^3
• Polar Surface Area: 108.19 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 170-172°C

DETAILS

Toronto Research Chemicals - C441660

Impurity C of Cimetidine.

REFERENCES

• Durant, G.J., et al.: J. Med. Chem., 18, 830 (1975)
• Pounder, R.E., et al.: Br. Med. J., 2, 307 (1975)