Chemistry:Morpheridine
 | |
| Clinical data | |
|---|---|
| ATC code |
|
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| Chemical and physical data | |
| Formula | C20H30N2O3 |
| Molar mass | 346.471 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
Morpheridine (Morpholinoethylnorpethidine)[1] is a 4-phenylpiperidine 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,[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
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
- ↑ Stern ES, Anderson RJ, "Piperidine Compounds and Their Production", US patent 2795581, issued 06/11/1957, assigned to J.F. McFarlan & Co
- ↑ "Morpholinoethylnorpethidine hydrochloride in obstetrics". The Journal of Obstetrics and Gynaecology of the British Empire 65 (1): 98–9. February 1958. doi:10.1111/j.1471-0528.1958.tb06218.x. PMID 13514558.
- ↑ "Analgesic and other properties of morpholinoethylnorpethidine". British Journal of Pharmacology and Chemotherapy 11 (1): 32–4. March 1956. doi:10.1111/j.1476-5381.1956.tb01023.x. PMID 13304251.
- ↑ "Single convention on drugs 1961". http://www.ukcia.org/pollaw/lawlibrary/singleconventiononnarcoticdrugs1961.php.
- ↑ "Search for new analgesics; further homologues of pethidine and the pharmacology of these and other compounds". Journal of the Chemical Society 2: 559–61. May 1948. doi:10.1039/JR9480000559. PMID 18869425.
- ↑ "788. Some new analogues of pethidine. Part I". Journal of the Chemical Society (Resumed): 4088. 1956. doi:10.1039/JR9560004088.
 |  |
