1-methyl-2-[(E)-2-(3-methylthiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine; 2-hydroxypropane-1,2,3-tricarboxylic acid

• ChemBase ID: 132868
• Molecular Formular: C18H24N2O7S
• Molecular Mass: 412.45736
• Monoisotopic Mass: 412.13042212
• SMILES: Cc1ccsc1/C=C/C1=NCCCN1C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Canonical SMILES: CN1CCCN=C1/C=C/c1sccc1C.OC(=O)CC(C(=O)O)(CC(=O)O)O
• InChI: InChI=1S/C12H16N2S.C6H8O7/c1-10-6-9-15-11(10)4-5-12-13-7-3-8-14(12)2;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-6,9H,3,7-8H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b5-4+
• InChIKey: OLOCXIJVDIVAHH-FXRZFVDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-2-[(E)-2-(3-methylthiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine; 2-hydroxypropane-1,2,3-tricarboxylic acid
• IUPAC Traditional name: citro; morantel
• Synonyms: 1,4,5,6-Tetrahydro-1-methyl-2-(2-[3-methyl-2-thienyl]ethenyl)pyrimidine; Morantel citrate salt

Database IDs

• CAS Number: 69525-81-1
• EC Number: 274-028-9
• MDL Number: MFCD00079447
• PubChem SID: 162227145
• PubChem CID: 5702276

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.062200725
• LogD (pH = 7.4): 0.11304529
• Log P: 2.476971
• Molar Refractivity: 66.8548 cm^3
• Polarizability: 24.59202 Å^3
• Polar Surface Area: 15.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

DETAILS

Sigma Aldrich - M5404

Application
Morantel is a anthelmintic compound used to treat parasitic infections in livestock1. It is also used to study allosteric potentiation of rat neuronal nicotinic acetylcholine receptors (nAChRs)1 and is used to study nematode nicotinic receptors2.
Biochem/physiol Actions
Morantel is a potent non-canonical (binding site) acetylcholine (ACh) receptor agonist and inhibits fumarate reductase. Morantel increases the macroscopic currents evoked by acetylcholine (ACh) from nAChRs expressed in Xenopus laevis oocytes up to 8 times1.
Morantel is a potent non-canonical (binding site) acetylcholine (ACh) receptor agonist and inhibits fumarate reductase.