Morpheridine

Morpheridine
Clinical data
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Controlled Drug; US: Schedule I; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name ethyl 1-(2-morpholin-4-ylethyl)-4-phenyl-piperidine-4-carboxylate;
CAS Number	469-81-8 ;
PubChem CID	61121;
ChemSpider	55069 ;
UNII	1854GKB41Y;
CompTox Dashboard (EPA)	DTXSID20196979 ;
ECHA InfoCard	100.006.749
Chemical and physical data
Formula	C20H30N2O3
Molar mass	346.471 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(verify)

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

Morpheridine is not currently used in medicine and is a Schedule I drug which is controlled under UN drug conventions.^[5]

Synthesis

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.^[7]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ US 2795581, Stern ES, Anderson RJ, "Piperidine Compounds and Their Production", issued 06/11/1957, assigned to J.F. McFarlan & Co
^ Holmes JM (February 1958). "Morpholinoethylnorpethidine hydrochloride in obstetrics". The Journal of Obstetrics and Gynaecology of the British Empire. 65 (1): 98–9. doi:10.1111/j.1471-0528.1958.tb06218.x. PMID 13514558. S2CID 1481693.
^ Green AF, Ward NB (March 1956). "Analgesic and other properties of morpholinoethylnorpethidine". British Journal of Pharmacology and Chemotherapy. 11 (1): 32–4. doi:10.1111/j.1476-5381.1956.tb01023.x. PMC 1509567. PMID 13304251.
^ "Single convention on drugs 1961".
^ Thorp RH, Walton E (May 1948). "Search for new analgesics; further homologues of pethidine and the pharmacology of these and other compounds". Journal of the Chemical Society. 2: 559–61. doi:10.1039/JR9480000559. PMID 18869425.
^ Anderson RJ, Frearson PM, Stern ES (1956). "788. Some new analogues of pethidine. Part I". Journal of the Chemical Society (Resumed): 4088. doi:10.1039/JR9560004088.

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[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] US 2795581, Stern ES, Anderson RJ, "Piperidine Compounds and Their Production", issued 06/11/1957, assigned to J.F. McFarlan & Co

[3] Holmes JM (February 1958). "Morpholinoethylnorpethidine hydrochloride in obstetrics". The Journal of Obstetrics and Gynaecology of the British Empire. 65 (1): 98–9. doi:10.1111/j.1471-0528.1958.tb06218.x. PMID 13514558. S2CID 1481693.

[4] Green AF, Ward NB (March 1956). "Analgesic and other properties of morpholinoethylnorpethidine". British Journal of Pharmacology and Chemotherapy. 11 (1): 32–4. doi:10.1111/j.1476-5381.1956.tb01023.x. PMC 1509567. PMID 13304251.

[5] "Single convention on drugs 1961".

[6] Thorp RH, Walton E (May 1948). "Search for new analgesics; further homologues of pethidine and the pharmacology of these and other compounds". Journal of the Chemical Society. 2: 559–61. doi:10.1039/JR9480000559. PMID 18869425.

[7] Anderson RJ, Frearson PM, Stern ES (1956). "788. Some new analogues of pethidine. Part I". Journal of the Chemical Society (Resumed): 4088. doi:10.1039/JR9560004088.

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Synthesis

See also

References