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

• ChemBase ID: 155355
• Molecular Formular: C17H22N2O7S
• Molecular Mass: 398.43078
• Monoisotopic Mass: 398.11477205
• SMILES: CN1CCCN=C1/C=C/c1cccs1.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Canonical SMILES: CN1CCCN=C1/C=C/c1cccs1.OC(=O)CC(C(=O)O)(CC(=O)O)O
• InChI: InChI=1S/C11H14N2S.C6H8O7/c1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10;7-3(8)1-6(13,5(11)12)2-4(9)10/h2,4-6,9H,3,7-8H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
• InChIKey: YJGGCARNRYGSPA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-2-[2-(thiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine; 2-hydroxypropane-1,2,3-tricarboxylic acid
• IUPAC Traditional name: citro; pyrantel
• Synonyms: 1-Methyl-2-(2-[2-thienyl]ethenyl)-1,4,5,6-tetrahydropyrimidine; Pyrantel citrate salt

Database IDs

• CAS Number: 5685-86-9
• EC Number: 227-154-3
• MDL Number: MFCD00079269
• PubChem SID: 162249493
• PubChem CID: 6436405

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.45122287
• LogD (pH = 7.4): -0.40053108
• Log P: 1.9635495
• Molar Refractivity: 61.8136 cm^3
• Polarizability: 22.833937 Å^3
• Polar Surface Area: 15.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H319-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Product Information

• Empirical Formula (Hill Notation): C11H14N2S · C6H8O7

DETAILS

Sigma Aldrich - P7549

Application
Pyrantel is an antinematodal thiophene. It is commonly used by veterinarians to treat and prevent intestinal parasites in small animals. It has been used to phenotypically characterize Ancylostoma caninum isolates1 and is used to distinguish cholinergic receptor subtypes in Ascaris muscle2.
Biochem/physiol Actions
Pyrantel is a nematode muscle cell-associated nicotinic agonist for the acetylcholine (ACh) receptor. Cholinesterase inhibitor.
Pyrantel is a nematode muscle cell-associated nicotinic agonist for the acetylcholine (ACh) receptor. This is a cholinesterase inhibitor. It causes muscle paralysis in parasitic worms due to prolonged activation of the excitatory nicotinic acetylcholine (nACh) receptors.