Synthesis and Pharmacological Activities of  Capsaicin Analogues I: Sodium NonivamideAcetate and Sodium Nonivamide Propionate as Potential Antinociceptive Agents

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Title:	Synthesis and Pharmacological Activities of Capsaicin Analogues I: Sodium NonivamideAcetate and Sodium Nonivamide Propionate as Potential Antinociceptive Agents 番椒晶素同類物之合成與藥理作用 I：為具有淺力之抗傷痛劑
Authors:	Jwu-Maw Yang Yen-Nien Hsu Shiow-Lin Pan Bin-Nan Wu Ing-Jun Chen
Contributors:	藥學科
Keywords:	Capsaicin analogues Antinociceptive Naloxone
Date:	1991
Issue Date:	2011-01-04 16:44:59 (UTC+8)
Abstract:	Two ether-linked analogues of capsaicin (CAP), sodium N-nonanoyl vanillylamide-4-0-acetate (sodium nonivamide acetate; SNA) and sodium N-nonanoyl vanillylamide-4-0-propionate (sodium nonivamide propionate; SNP), were synthesized by alkylation of the phenolic hydroxyl group of N-nonanoyl vanillylamide (nonivamide; NVA) with bromoacetic acid and /3-bromopropionic acid in the presence of sodium hydroxide, respectively. Both analogues revealed marked antinociceptive activities in the acetic acid-induced writhing test in mice without producing overt pungent sensation and irritation that have been found in CAP and NVA. Concomitant administration with opioid antagonist naloxone (NAL) did not block the antinociceptive activities of these two analogues, the opiate recept.or-mechanism is thus excluded. The reults of acute toxicity test also demonstratpd that both analogues were .elatively non-toxic as compared to CAP or NVA. 以溴化乙酸及B-溴化丙酸在氫氧化鈉存在下，，烷化N-香草素基人覈胺(N-nonanoyl vanil-lylamide; nonivamide;NVA)之酚性羫基，分別得到兩種醚鍵結的番椒晶素(capsaicin;CAP)同類物，即N-香草素基壬醯胺-4'-氧-乙酸鈉(sodium N-nonanoyl vanillylamidePropionate; sodium nonivamide propionate; SNP)。此兩種同類物在醋酸誘發小白鼠之扭痛實驗中呈現顯著的抗傷痛活性，但並不產生如CCAP與NVA所引起的辣感，刺激性。在同時施予鴉片類拮抗劑naloxone (NAL)後並不阻斷此兩種同類物之抗傷痛活性，因此排除了鴉片劑接受體之機轉。由急性毒性試驗的結果顯示此兩種同類物與與CAP及NVA比較，相對地不具毒性。
Relation:	嘉南學報 17期 : p.A73-A83 轉載中華藥學雜誌 43(4) (1991)
Appears in Collections:	[Chna Nan Annual Bulletin] Vol.17 (1991) [Dept. of Pharmacy] Periodical Articles

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