(Z)-Capsaicin

(Z)-Capsaicin is an alkaloid that has been found in Capsicum, has diverse biological activities, and is the cis-isomer of capsaicin (Cay-92350, Cay-10010743). It is an agonist of transient receptor potential vanilloid 1 (TRPV1), inducing calcium uptake in CHO cells expressing human TRPV1 (EC50 = 28.2 nM). (Z)-Capsaicin (10 µM) shortens the action potential duration in isolated canine Purkinje fibers. It increases the latency to paw withdrawal in the hot plate test in rats when administered at a dose of 0.68 mmol/animal. Topical application of (Z)-capsaicin (25 µl of a 1% solution) reduces croton oil-induced ear edema in mice. It induces emesis in musk shrews (S. murinus). (Z)-Capsaicin decreases disease severity in a guinea pig model of genital herpes induced by herpes simplex virus 2 (HSV-2). Formulations containing (Z)-capsaicin have been used in the treatment of osteoarthritis and neuropathic pain.Formal Name: N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide. CAS Number: 25775-90-0. Synonyms: cis-Capsaicin, cis-8-methyl-N-Vanillyl-6-nonenamide, Zucapsaicin. Molecular Formula: C18H27NO3. Formula Weight: 305.4. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: DMSO: Soluble, Methanol: Soluble. SMILES: OC1=C(OC)C=C(CNC(CCCC/C=C\C(C)C)=O)C=C1. InChi Code: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6-. InChi Key: YKPUWZUDDOIDPM-VURMDHGXSA-N. Origin: Synthetic.