Мы используем файлы cookie.
Продолжая использовать сайт, вы даете свое согласие на работу с этими файлами.
Mu-opioid receptor agonists
Morpheridine
Другие языки:

Morpheridine

Подписчиков: 0, рейтинг: 0
Morpheridine
Morpheridine2DCSD.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • ethyl 1-(2-morpholin-4-ylethyl)-4-phenyl-piperidine-4-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.749
Chemical and physical data
Formula C20H30N2O3
Molar mass 346.471 g·mol−1
3D model (JSmol)
  • O=C(OCC)C3(c1ccccc1)CCN(CCN2CCOCC2)CC3
  • 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 checkY
  • Key:JDEDMCKQPKGSAX-UHFFFAOYSA-N checkY
  (verify)

Morpheridine (Morpholinoethylnorpethidine) 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, and unlike pethidine, does not cause convulsions, although it produces the standard opioid side effects such as sedation and respiratory depression.

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

Synthesis

Normeperidine 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.

See also


Новое сообщение