(Z)-Capsaicin

(Z)-Capsaicin is an alkaloid that has been found in Capsicum, has diverse biological activities, and is the cis-isomer of capsaicin (Item Nos. 92350 | 10010743).^1,2,3,4,5,6 It is an agonist of transient receptor potential vanilloid 1 (TRPV1), inducing calcium uptake in CHO cells expressing human TRPV1 (EC₅₀ = 28.2 nM).² (Z)-Capsaicin (10 µM) shortens the action potential duration in isolated canine Purkinje fibers.³ It increases the latency to paw withdrawal in the hot plate test in rats when administered at a dose of 0.68 mmol/animal.⁴ 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).⁵ (Z)-Capsaicin decreases disease severity in a guinea pig model of genital herpes induced by herpes simplex virus 2 (HSV-2).⁶ Formulations containing (Z)-capsaicin have been used in the treatment of osteoarthritis and neuropathic pain.

WARNING This product is not for human or veterinary use.

1. Espichán, F., Rojas, R., Quispe, F., et al. Metabolomic characterization of 5 native Peruvian chili peppers (Capsicum spp.) as a tool for species discrimination. Food Chem. 386, 132704 (2022).

2. Ann, J., Kim, H.S., Thorat, S.A., et al. Discovery of nonpungent transient receptor potential vanilloid 1 (TRPV1) agonist as strong topical analgesic. J. Med. Chem. 63(1), 418-424 (2020).

3. Arnar, D.O., Cai, J.J., Lee, H.-C., et al. Electrophysiologic effects of civamide (zucapsaicin) on canine cardiac tissue in vivo and in vitro. J. Cardiovasc. Pharmacol. 32(6), 875-883 (1998).

4. Janusz, J.M., Buckwalter, B.L., Young, P.A., et al. Vanilloids. 1. Analogs of capsaicin with antinociceptive and antiinflammatory activity. J. Med. Chem. 36, 2595-2604 (1993).

5. Rudd, J.A., and Wai, M.K. Genital grooming and emesis induced by vanilloids in Suncus murinus, the house musk shrew. Eur. J. Pharmacol. 422(1-3), 185-195 (2001).

6. Bourne, N., Bernstein, D.I., and Stanberry, L.R. Civamide (cis-capsaicin) for treatment of primary or recurrent experimental genital herpes. Antimicrob. Agents Chemother. 43(11), 2685-2688 (1999).