N-[4-(4-chlorophenyl)-3-methylbut-3-en-2-ylidene]hydroxylamine

• ChemBase ID: 154498
• Molecular Formular: C11H12ClNO
• Molecular Mass: 209.67208
• Monoisotopic Mass: 209.06074169
• SMILES: C/C(=C/c1ccc(cc1)Cl)/C(=N/O)/C
• Canonical SMILES: O/N=C(/C(=C\c1ccc(cc1)Cl)/C)\C
• InChI: InChI=1S/C11H12ClNO/c1-8(9(2)13-14)7-10-3-5-11(12)6-4-10/h3-7,14H,1-2H3
• InChIKey: MHTJEUOFLVQMCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-(4-chlorophenyl)-3-methylbut-3-en-2-ylidene]hydroxylamine
• IUPAC Traditional name: N-[4-(4-chlorophenyl)-3-methylbut-3-en-2-ylidene]hydroxylamine
• Synonyms: 4-(4-Chlorophenyl)-3-methylbut-3-en-2-oxime; AP-18

Database IDs

• CAS Number: 55224-94-7
• MDL Number: MFCD00102250
• PubChem SID: 162248637
• PubChem CID: 16725814

CALCULATED PROPERTIES

• Acid pKa: 10.462163
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4745417
• LogD (pH = 7.4): 3.4744062
• Log P: 3.4747868
• Molar Refractivity: 59.5946 cm^3
• Polarizability: 22.643406 Å^3
• Polar Surface Area: 32.59 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H12ClNO

DETAILS

Sigma Aldrich - A7232

Application
AP-18 is a selective TRPA1 channel blocker. AP-18 blocks the transient receptor potential ankyrin 1 receptors and can reduce chronic pain associated with arthritis. AP-18 reduces cinnamaldehyde-induced nociception in vivo and blocks cold- and mustard oil-induced activation of mouse TRPA1 but not capsaicin-induced activation. AP-18 reverses CFA-induced mechanical hyperalgesia in mice
Biochem/physiol Actions
AP-18 is a selective TRPA1 channel blocker. Transient receptor potential A1 (TRPA1) plays a central role for chemical sensing in the pain pathway. AP-18 is a novel TRPA1 channel blocker. It reduces cinnamaldehyde-induced nociception in vivo and blocks cold- and mustard oil-induced activation of mouse TRPA1 but not capsaicin-induced activation demonstrating selectivity vs. TRPV11. AP-18 reverses CFA-induced mechanical hyperalgesia in mice.