(2S,3S)-N-[(5-tert-butyl-2-methoxyphenyl)methyl]-2-(diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-amine

• ChemBase ID: 172553
• Molecular Formular: C32H40N2O
• Molecular Mass: 468.6728
• Monoisotopic Mass: 468.31406391
• SMILES: C1CC2[C@@H]([C@@H](N1CC2)C(c1ccccc1)c1ccccc1)NCc1c(ccc(c1)C(C)(C)C)OC
• Canonical SMILES: COc1ccc(cc1CN[C@H]1C2CCN([C@H]1C(c1ccccc1)c1ccccc1)CC2)C(C)(C)C
• InChI: InChI=1S/C32H40N2O/c1-32(2,3)27-15-16-28(35-4)26(21-27)22-33-30-25-17-19-34(20-18-25)31(30)29(23-11-7-5-8-12-23)24-13-9-6-10-14-24/h5-16,21,25,29-31,33H,17-20,22H2,1-4H3/t30-,31-/m0/s1
• InChIKey: OMPCVMLFFSQFIX-CONSDPRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-N-[(5-tert-butyl-2-methoxyphenyl)methyl]-2-(diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-amine
• IUPAC Traditional name: maropitant
• Synonyms: (2S-cis)-N-[[5-(1,1-Dimethylethyl)-2-methoxyphenyl]methyl]-2-(diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-amine Citrate Salt; (2S,3S)-2-Benzhydryl-N-(5-tert-butyl-2-methoxybenzyl)quinuclidin-3-amine Citrate Salt; Maropitant Citrate Salt

Database IDs

• CAS Number: 147116-67-4
• PubChem SID: 164228463
• PubChem CID: 204108

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.1602793
• LogD (pH = 7.4): 4.5806456
• Log P: 6.866307
• Molar Refractivity: 146.0098 cm^3
• Polarizability: 57.521454 Å^3
• Polar Surface Area: 24.5 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M197300

Maropitant is a neurokinin type 1 (NK-1) receptor antagonist. Recent studies show that Maropitant decreased the anesthetic requirements during visceral stimulation of the ovary and ovarian ligament in dogs.

REFERENCES

• Boscan, P. et al.: Am. J. Vet. Res., 72, 1576 (2011)