Morpheridine

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Morpheridine
Morpheridine2DCSD.svg
Systematic (IUPAC) name
ethyl 1-(2-morpholin-4-ylethyl)-4-phenyl-piperidine-4-carboxylate
Clinical data
Identifiers
469-81-8 YesY
None
PubChem CID 61121
ChemSpider 55069 YesY
UNII 1854GKB41Y YesY
Chemical data
Formula C20H30N2O3
346.46 g/mol
 YesY (what is this?)  (verify)

Morpheridine (Morpholinoethylnorpethidine)[1] is a 4-phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine). It is a strong analgesic with around 4 times the potency of pethidine,[2] and unlike pethidine, does not cause convulsions, although it produces the standard opioid side effects such as sedation and respiratory depression.[3]

Morpheridine is not currently used in medicine and is a Schedule I drug which is controlled under UN drug conventions.[4]

Synthesis[edit]

Normeperidine synthesis:[5]

The key intermediate, normeperidine, is obtained by a scheme closely akin to the parent molecule. Thus, alkylation of benzyl cyanide (1) with the tosyl analog of the bischloroethylamine (2) leads to the substituted piperidine (3). Basic hydrolysis serves to convert the nitrile to the acid (4). Treatment of this last with sulfuric acid in ethanol serves both to esterify the acid and to remove the tosyl group to yield the secondary amine (5).

Alkylation of that amine by means of N-(2-chloroethyl)morpholine gives morpheridine.[6]

See also[edit]

References[edit]

  1. ^ US 2795581, STERN EDWARD S; ANDERSON RONALD J, "Piperidine Compounds and Their Production", issued 06/11/1957, assigned to J.F. McFarlan & Co 
  2. ^ Holmes, J. M. (1958). "Morpholinoethylnorpethidine hydrochloride in obstetrics". The Journal of obstetrics and gynaecology of the British Empire 65 (1): 98–99. doi:10.1111/j.1471-0528.1958.tb06218.x. PMID 13514558.  edit
  3. ^ Green, A. F.; Ward, N. B. (1956). "Analgesic and other properties of morpholinoethylnorpethidine". British journal of pharmacology and chemotherapy 11 (1): 32–34. PMC 1509567. PMID 13304251.  edit
  4. ^ "Single convention on drugs 1961". 
  5. ^ Thorp, R. H.; Walton, E. (1948). "114. Search for new analgesics. Part II. Further homologues of pethidine and the pharmacology of these and other compounds". Journal of the Chemical Society (Resumed): 559. doi:10.1039/JR9480000559.  edit
  6. ^ Anderson, R. J.; Frearson, P. M.; Stern, E. S. (1956). "788. Some new analogues of pethidine. Part I". Journal of the Chemical Society (Resumed): 4088. doi:10.1039/JR9560004088.  edit