Nonivamide

Nonivamide is a transient receptor potential vanilloid type 1 (TRPV1) agonist and an analog of capsaicin (Cay-92350, Cay-10010743) that has been isolated from Capsicum species. It is toxic to NHBE, BEAS-2B, and BEAS-2B cells overexpressing TRPV1 (TRPV1-OE, LC50s = 160, 115, and 1 µM, respectively), increases calcium flux in TRPV1-OE cells (EC50 = 1.4 µM), and increases GADD153 mRNA expression by 7- and 6-fold when used at concentrations of 2 and 20 µM, respectively. Nonivamide (1 µM) also increases the release of dopamine and serotonin from SH-SY5Y cells in a calcium-dependent and TRPV1-independent manner. In mice, it reduces respiration when inhaled and is toxic with LD50 values of 200 and 413 mg/kg for oral and inhaled administration, respectively. Formulations containing nonivamide have been used in pepper spray weaponry for riot control.Formal Name: N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide. CAS Number: 2444-46-4. Synonyms: Nonanoic Acid Vanillylamide, NSC 172795, Pelargonic Acid Vanillylamide, Pseudocapsaicin, N-Vanillylnonanamide, N-Vanillylpelargonamide. Molecular Formula: C17H27NO3. Formula Weight: 293.4. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: 0.1 M Na2CO3: 1 mg/ml, DMF: 15 mg/ml, DMSO: 13 mg/ml, Ethanol: 31 mg/ml. lambdamax: 228 nm. SMILES: COC1=C(O)C=CC(CNC(CCCCCCCC)=O)=C1. InChi Code: InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20). InChi Key: RGOVYLWUIBMPGK-UHFFFAOYSA-N.