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去甲哌替啶

维基百科，自由的百科全书
去甲哌替啶
临床资料
给药途径N/A
ATC码
  • 未分配
法律规范状态
法律规范
识别信息
  • Ethyl 4-phenylpiperidine-4-carboxylate
CAS号77-17-8  checkY
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)
ECHA InfoCard100.000.918 编辑维基数据链接
化学信息
化学式C14H19NO2
摩尔质量233.31 g·mol−1
3D模型（JSmol（英语：JSmol））
  • O=C(OCC)C2(c1ccccc1)CCNCC2
  • InChI=1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3 checkY
  • Key:QKHMFBKXTNQCTM-UHFFFAOYSA-N checkY

去甲哌替啶是一种4-苯基哌啶的衍生物，化学式为C14H19NO2。它是哌替啶的前体及有毒代谢物。它被列入联合国麻醉品单一公约，也被美国列入到受管制物质法案附表II，2014年的生产限额为11克（0.39盎司）。[1]

去甲哌替啶因可用于合成哌替啶及相关的N-取代衍生物（如依托利定（英语：etoxeridine）[2]、苄替啶（英语：benzethidine）[3]、呋替啶（英语：furethidine）[4]）而受到管制。不过，去甲哌替啶本身的类阿片作用低，是一种引起抽搐的兴奋剂。[5][6]

当把哌替啶用作镇痛药时，就要大剂量使用[7]或静脉注射哌替啶。[8]这会去甲哌替啶产生的速率比排泄去甲哌替啶的速率快，导致去甲哌替啶累积产生的并发症，包括抽搐、肌阵挛[9]、低血钠症。[10]这些并发症可能会很严重，甚至可能导致死亡。[11]这些并发症在老年人[12]及肝功能或肾功能受损的人[13]身上更明显。

哌替啶在体内会被肝脏属于细胞色素P450的CYP2B6、CYP2C19、CYP3A4代谢成去甲哌替啶。由于这些酶的活性因人而异，且可能受到共服的其它药物影响，因此很难预测产生去甲哌替啶的速率。[14][15]

参考资料

  1. ^ Conversion Factors for Controlled Substances. Diversion Control Division. Drug Enforcement Administration (DEA), U.S. Department of Justice. [2024-03-13]. （原始内容存档于2016-03-02）. 
  2. ^ US granted 2858316,Henri M,“New piperidine derivatives”,发表于28 October 1958,指定于UCB SA 
  3. ^ Frearson PM, Stern ES. 622. Some new analogues of pethidine. Part III. 1-Aryloxy-alkylnorpethidines, and close analogues.. Journal of the Chemical Society (Resumed). 1958: 3065–7. doi:10.1039/JR9580003065. 
  4. ^ Frearson PM, Hardy DG, Stern ES. 426. Some new analogues of pethidine. Part IV. Substituents at the 1-position incorporating cyclic ether groups.. Journal of the Chemical Society (Resumed). 1960: 2103–7. doi:10.1039/JR9600002103. 
  5. ^ Umans JG, Inturrisi CE. Antinociceptive activity and toxicity of meperidine and normeperidine in mice. The Journal of Pharmacology and Experimental Therapeutics. October 1982, 223 (1): 203–6 [2024-03-13]. PMID 7120119. （原始内容存档于2024-03-13）. 
  6. ^ Plummer JL, Gourlay GK, Cmielewski PL, Odontiadis J, Harvey I. Behavioural effects of norpethidine, a metabolite of pethidine, in rats. Toxicology. January 1995, 95 (1–3): 37–44. PMID 7825188. doi:10.1016/0300-483x(94)02871-q. 
  7. ^ Simopoulos TT, Smith HS, Peeters-Asdourian C, Stevens DS. Use of meperidine in patient-controlled analgesia and the development of a normeperidine toxic reaction. Archives of Surgery (Chicago, Ill.). January 2002, 137 (1): 84–8. PMID 11772223. doi:10.1001/archsurg.137.1.84 可免费查阅. 
  8. ^ Stone PA, Macintyre PE, Jarvis DA. Norpethidine toxicity and patient controlled analgesia. British Journal of Anaesthesia. November 1993, 71 (5): 738–40. PMID 8251291. doi:10.1093/bja/71.5.738 可免费查阅. 
  9. ^ Reutens DC, Stewart-Wynne EG. Norpethidine induced myoclonus in a patient with renal failure. Journal of Neurology, Neurosurgery, and Psychiatry. December 1989, 52 (12): 1450–1. PMC 1031622 可免费查阅. PMID 2614458. doi:10.1136/jnnp.52.12.1450. 
  10. ^ Appel WC. Possible roles of normeperidine and hyponatremia in a postoperative death. Canadian Medical Association Journal. November 1987, 137 (10): 912–3. PMC 1267380 可免费查阅. PMID 3676934. 
  11. ^ Jiraki K. Lethal effects of normeperidine. The American Journal of Forensic Medicine and Pathology. March 1992, 13 (1): 42–3. PMID 1585886. S2CID 32005631. doi:10.1097/00000433-199203000-00009. 
  12. ^ Holmberg, L.; Odar-Cederlöf, I.; Boréus, L. O.; Heyner, L.; Ehrnebo, M. Comparative disposition of pethidine and norpethidine in old and young patients. European Journal of Clinical Pharmacology. 1982, 22 (2): 175–179. ISSN 0031-6970. doi:10.1007/BF00542464. 
  13. ^ Pond SM, Tong T, Benowitz NL, Jacob P, Rigod J. Presystemic metabolism of meperidine to normeperidine in normal and cirrhotic subjects. Clinical Pharmacology and Therapeutics. August 1981, 30 (2): 183–8. PMID 7249503. S2CID 10117158. doi:10.1038/clpt.1981.146. 
  14. ^ Ramírez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ. CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metabolism and Disposition: The Biological Fate of Chemicals. September 2004, 32 (9): 930–6. PMID 15319333. 
  15. ^ McHugh GJ. Norpethidine accumulation and generalized seizure during pethidine patient-controlled analgesia. Anaesthesia and Intensive Care. June 1999, 27 (3): 289–91. PMID 10389564. 

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