Morpheridine

Morpheridine

Systematic (IUPAC) name
ethyl 1-(2-morpholin-4-ylethyl)-4-phenyl-piperidine-4-carboxylate
Clinical data
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) UK: Controlled Drug US: Schedule I UN: Psychotropic Schedule I
Identifiers
CAS Number	469-81-8
ATC code	none
PubChem	CID 61121
ChemSpider	55069
UNII	1854GKB41Y
Chemical data
Formula	C20H30N2O3
Molar mass	346.46 g/mol
SMILES O=C(OCC)C3(c1ccccc1)CCN(CCN2CCOCC2)CC3
InChI InChI=1S/C20H30N2O3/c1-2-25-19(23)20(18-6-4-3-5-7-18)8-10-21(11-9-20)12-13-22-14-16-24-17-15-22/h3-7H,2,8-17H2,1H3 Key:JDEDMCKQPKGSAX-UHFFFAOYSA-N
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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

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

• Anileridine
• Furethidine
• Carbetidine

References

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.
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.
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.
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.