Norpethidine

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

Template:Short description Template:Drugbox

Norpethidine (normeperidine, pethidine intermediate B) is a 4-phenylpiperidine derivative that is both a precursor to, and the toxic metabolite of, pethidine (meperidine). It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9233. The 2014 annual manufacturing quota was Script error: No such module "convert"..[1]

Norpethidine is a controlled drug because of its potential uses in manufacturing both pethidine itself and a range of N-substituted derivatives, but it has little opioid activity in its own right. Instead, norpethidine acts as a stimulant and causes convulsions.[2][3]

Bioaccumulation of norpethidine is a major complication when pethidine is used in medicine as an analgesic, as when pethidine is used in high doses[4] or administered by intravenous infusion,[5] norpethidine can accumulate in the body at a faster rate than it is being excreted, particularly in elderly patients[6] or those with compromised liver or kidney function,[7] resulting in a range of toxic effects, mainly convulsions, but also myoclonus[8] and hyponatremia.[9] These complications can be serious and have sometimes resulted in death.[10]

Metabolism of pethidine to norpethidine is carried out mainly by the CYP enzymes, CYP2B6, CYP2C19 and CYP3A4, in the liver, and since the activity of these enzymes can vary between individuals and can be influenced by concurrent use of other drugs, the rate and extent of norpethidine production can be difficult to predict.[11][12]

Precursor Use

Norpethidine can be used as a precursor in synthesis of other drugs, including etoxeridine,[13] benzethidine,[14] furethidine,[15] morpheridine, anileridine, phenoperidine, piminodine, oxpheneridine, pheneridine & carperidine.

Legitimate research chemical uses include: R 951[16][17][18][19] R 1187,[20] R 1204,[20][21] R 1133,[20] R 960[20] PCP-hybrid (121019-93-0),[22] amitriptyline-hybrid.[23][24][25][26][27] >6 hr duration patent: PC20975957[28] (c.f. 3,3-Diphenylpropylamine)

See also

References

<templatestyles src="Reflist/styles.css" />

  1. ↑ Script error: No such module "citation/CS1".
  2. ↑ Script error: No such module "Citation/CS1".
  3. ↑ Script error: No such module "Citation/CS1".
  4. ↑ Script error: No such module "Citation/CS1".
  5. ↑ Script error: No such module "Citation/CS1".
  6. ↑ Holmberg L, Odar-Cederlof I, Boreus LO, Heyner L, Ehrnebo M. Comparative disposition of pethidine and norpethidine in old and young patients. European Journal of Clinical Pharmacology. 1982;22(2):175-9.
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Henri M, "New piperidine derivatives", published Script error: No such module "auto date formatter"., assigned to UCB SA Script error: No such module "Check for unknown parameters".
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Script error: No such module "Citation/CS1".
  16. ↑ Janssen, Paul A. J.; Jageneau, Anton H. M.; Demoen, Paul J. A.; Westeringh, Corn. van De.; Raeymaekers, Alfons H. M.; Wouters, Maria S. J.; Sanczuk, Stefan; Hermans, Bert K. F.; Loomans, Jozef L. M. (1959). "Compounds Related to Pethidine--I. Mannich Bases Derived from Norpethidine and Acetophenones". Journal of Medicinal and Pharmaceutical Chemistry. 1 (1): 105–120. doi:10.1021/jm50002a008.
  17. ↑ Janssen, Paul A. J.; Jageneau, Anton H. M.; Demoen, Paul J. A.; van De Westeringh, Corn.; De Canniere, Julienne H. M.; Raeymaekers, Alfons H. M.; Wouters, Maria S. J.; Sanczuk, Stefan; Hermans, Bert K. F. (2002). "Compounds Related to Pethidine--II. Mannich Bases Derived from Various Esters of 4-Carboxy-4-phenylpiperidine and Acetophenones". Journal of Medicinal and Pharmaceutical Chemistry. 1 (4): 309–317. doi:10.1021/jm50005a002.
  18. ↑ Pohland Albert, US2951080 (1960 to Eli Lilly and Co).
  19. ↑ Jr Frank A Cutler & James F Fisher, US2962501 (1960 to Merck and Co Inc).
  20. ↑ a b c d Janssen, Paul; Jageneau, Anton H. M.; Demoen, Paul J. A.; van De Westeringh, Corn.; De Canniere, Julienne H. M.; Raeymaekers, Alfons H. M.; Wouters, Maria; Sanczuk, Stefan; Hermans, Bert K. F. (1960). "Compounds Related to Pethidine--III. Basic Ketones derived from Norpethidine". Journal of Medicinal and Pharmaceutical Chemistry. 2 (3): 271–280. doi:10.1021/jm50010a003.
  21. ↑ Elpern Bill, US3093652 (1963 to STWB Inc).
  22. ↑ Itzhak Y, Kalir A, Weissman BA, Cohen S. New analgesic drugs derived from phencyclidine. J Med Chem. 1981 May;24(5):496-9. doi: 10.1021/jm00137a004. PMID: 7241506.
  23. ↑ Script error: No such module "Citation/CS1".
  24. ↑ Script error: No such module "Citation/CS1".
  25. ↑ Martin Arnold Davis & Stanley Oscar Winthrop, DE1200300 (1965 to Wyeth Canada Inc).
  26. ↑ A. Davis Martin & O. Winthrop Stanley, CA724166A (1965 to Wyeth Canada Inc).
  27. ↑ Martin A Davis & Stanley O Winthrop, U.S. patent 3074953 (1963 to Wyeth LLC).
  28. ↑ Gustav Ehrhart, Leopold Ther, Hans-Georg Alpermann, & Heinrich Ott, U.S. patent 3426028 (1969 to Hoechst AG).

Script error: No such module "Check for unknown parameters".

Template:Adrenergics Template:Dopaminergics Template:Serotonergics

Retrieved from "http://debianws.lexgopc.com/wiki143/index.php?title=Norpethidine&oldid=5707659"