Olvanil

Reductive amination of vanillin with ammonia leads to benzylamine 94. Acylation of that compound with (Z)-9-octadecenoyl chloride affords the analgesic olvanil (95) [23]. 

Ofloxacin, 141,142,144,145 Ofomine, 102 Olsalazine, 42 Olvanil, 35 Omeprazole, 133 Oral antidiabetic agent, 3 Oral contraceptives, 66, 68 Orange crush, 62 Organoplatinum complexes, 15 Oxagrelate, 151,152 Oxaprotiline, 63 Oxendolone, 66 Oximonam, 195... 

Olvanil (= A-Vanillyl-9- Synthetic (cf. Capsaicin) VAN-R agonist (Anandamide... 

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... 

Olive oil aromatized with chili pepper is a common condiment in the Mediterranean area. Under these conditions, transamidation of capsaicin to N-oleoylvanillamrne (olvanil, 69a) has been demonstrated [122]. Olvanil is nonpungent, but more potent as an anti-inflammatory agent than capsaicin, and one therefore wonders if olvanil might also contribute to the beneficial health effects traditionally attributed to olive oil flavored with hot pepper. 

Sabourin, C.L.K., Danne, M.M. et al. (2003). Modulation of sulfur mustard-induced inflammation and gene expression by Olvanil in the hairless mouse vesicant model. J. Toxicol. Cutan. Ocular Toxicol. 22(3) 125-36. 

Olvanil [inn, usan] (/V-vanillyloleamide) is a capsaicin analogue regarded as a vanilloid receptor AGONIST. It can be... 

Fig.3 Chemical structures of two vanilloid receptor agonists olvanil and capsaicin and of the vanilloid...

FIGURE 3.5 Percent inhibition of kainate activated current. The similar inhibitory effects of 2-AG and the synthetic endocannabinoid methanandamide are shown in oocytes expressing homomeric GluRl and GluR3 AMPA receptor. The effects of the endocaimabinoids were compared to arvanil and olvanil (vanilloid agonist) effects in the AMPA receptors and expressed as percentage inhibition of receptor currents in oocytes. 

Beltramo, M. and Piomelli, D. (1999) Anandamide transport inhibition by the vanilloid agonist olvanil, Eur. J. Pharmacol, 364 75-8. 

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