Capsaicin analogs

Y. Masuda, S. Haramizu, K. Oki, K. Ohnuki, T. Watanabe, S. Yazawa, T. Kawada, S. Hashzume and T. Fushiki, Upregulation of uncoupling proteins by oral administration of capsiate, a nonpungent capsaicin analog. /. Appl. Physiol, 2003, 95, 2408-2415. 

Cruz, F. Desensitization of bladder sensory fibers by intravesical capsaicin of capsaicin analogs, a new strategy for treatment of urge incontinence in patients with spinal detrusor hyperreflexia or bladder hypersensitivity disorders. Inter. Urogynecol. Journal 1998, 9, 214-220. 

Szallasi, A. and Blumberg, P.M. Specific binding of resiniferatoxin, an ultrapotent capsaicin analog, by dorsal root ganglion membranes, Brain Res. 1990a, 524, 106-111. 

Brand, L.M., Skare, K.L. et al. (1990). Anti-inflammatory pharmacology and mechanism of the orally active capsaicin analogs, NE-19550 and NE-28345. Agents Actions 31 329-40. 

Miller, M.S., Buck, S.H., Schnellmann, R., and Burks, T.F., Substance P depletion and analgesia induced by capsaicin analogs in guinea pigs, Fed. Proc., 40, 274, 1981. 

Andrews, P.L.R., Okada, F, Woods, A.J., Hagiwara, H., Kakaimoto, S., Toyoda, M., and Matsuki, N. (2000) The emetic and anti emetic affects of the capsaicin analog resiniferatoxin in Suncus murinus, the house musk shrew, Br. J. Pharmacol. 130 1247-1254. 

The vanilloid receptor is also known to be strongly affected by a capsaicin analog compoimd called resiniferatoxin, which was first isolated from a cactus-like plant Euphorbia resinifera). Lafutidine, an antacid, is more efficient against ulcers than other similar medicines, which may also be the consequence of an interaction with the vanilloid receptor. 

Similarly, most gases readily adsorb from the gas phase to form a bound gas, as a direct analogy to the adsorption of capsaicin... 

Birds may have a trigeminal receptor for o-aminoacetophenone and methyl anthranilate, analogous to the capsaicin receptor in mammals (Clark and Shah, 1994). 

Chemesthesis. The term chemesthesis has been introduced to classify thermal and painful sensations experienced in the mouth (26). Chemesthesis refers to a chemical sensibility (mouthfeel) in which certain chemicals direcdy activate nerve fibers at the level of the basal membrane in the mouth. The sensations are analogous to similar effects at the skin surface where there is a close anatomical and functional relationship. Sensations include the "hot" of capsaicin and piperine, which are active components of chili and pepper, the coolness of menthol and the irritation of chemicals such as salt at high concentrations [FIGURE 4]. Some of the descriptive terms used to make qualitative distinctions in food sensations include pungency, freshness, tingling, burning and sharpness. 

The formation of acyl conjugates of vanillamine (capsaicinoids, 20) or vanillic alcohol (capsinoids, 21) with various Cg/Ci3 alkenoic and alkanoic acids is a unique chemical trait of plants from the genus Capsicum. Hot peppers are characterized by the presence of vanillyl conjugates of the amide type, absent or replaced by their nonpungent ester isosters (capsinoids) in bell (sweet) peppers [19]. Indeed, the difference between the sensory properties of capsaicin (la) and its naturally occurring ester analog capsiate (22) is a remarkable example of the biological relevance of isosterism. 

Naturally Occurring Analogs and Antagonists of Capsaicin and Endogenous Vanilloids 193... 

The acyl moiety of capsaicin contains only one functional group, a double bond that is redundant for activity. On the contrary, the presence of the double bond is critical for the activity of olvanil, and interesting structure-activity relationships were discovered for this compound. Thus, an analog hydroxylated on the homoallylic carbon is easily available from the amidation of commercial and cheap ricinoleic... 

Szallasi, A., Blumherg, P.M. (1990). Resiniferatoxin and its analogs provide novel insights into the pharmacology of the vanilloid (capsaicin) receptor. Life Sci. 47 1399-408. 

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