N-(2,6-dichlorophenyl)-N-(prop-2-en-1-yl)-4,5-dihydro-1H-imidazol-2-amine

• ChemBase ID: 125678
• Molecular Formular: C12H13Cl2N3
• Molecular Mass: 270.15772
• Monoisotopic Mass: 269.04865279
• SMILES: Clc1cccc(Cl)c1N(C1=NCCN1)CC=C
• Canonical SMILES: C=CCN(c1c(Cl)cccc1Cl)C1=NCCN1
• InChI: InChI=1S/C12H13Cl2N3/c1-2-8-17(12-15-6-7-16-12)11-9(13)4-3-5-10(11)14/h2-5H,1,6-8H2,(H,15,16)
• InChIKey: OXTYVEUAQHPPMV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2,6-dichlorophenyl)-N-(prop-2-en-1-yl)-4,5-dihydro-1H-imidazol-2-amine
• IUPAC Traditional name: alinidine
• Synonyms: Alinidine; N-(2,6-Dichlorophenyl)-4,5-dihydro-N-2-propenyl-1H-imidazol-2-amine; ST-567; Alinidine

Database IDs

• CAS Number: 33178-86-8
• MDL Number: MFCD00864689
• PubChem SID: 24891193; 162220028
• PubChem CID: 36354
• CHEMBL: 278581
• Chemspider ID: 33429
• Unique Ingredient Identifier: E7IDJ8DS1D
• Wikipedia Title: Alinidine

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.1629667
• LogD (pH = 7.4): 2.5587137
• Log P: 3.3872712
• Molar Refractivity: 72.4863 cm^3
• Polarizability: 27.172962 Å^3
• Polar Surface Area: 27.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white solid

Safety Information

• Storage Condition: under inert gas
• RTECS: NJ1552500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Legal Status: Uncontrolled

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H13Cl2N3

DETAILS

Sigma Aldrich - A7230

Caution
Air-sensitive
Biochem/physiol Actions
Alinidine is an HCN Channel blocker of neuronal Ih, related cardiac If channels and ATP-sensitive Kir channels. It is an analog of clonidine; bradycardic and antiarrhythmic agent (sinus tachyarrhythmias). Alinidine affects physiological markers in conscious dogs. Alinidine in four intravenous (i.v.) injections of 0.5, 0.5, 1, and 2 mg/kg, decreased sinus rate (< or = 43%) and ventricular rate (< or = 44%), but increased atrial rate (< or = 31%). It lengthened CSRT (< or = 71%) at the two highest doses and increased AERP (< or = 33%) and decreased WP (< or = 33%) at all doses. Alinidine did not modify mean blood pressure at any dose in either group. These results indicate that alinidine exhibits electrophysiologic effects in conscious dogs that reflect the marked antiarrhythmic potential of this agent, apart from its assumed antiischemic properties.