Dextromoramide

Replacement of the ketone by an amide leads to Increased potency. Hydrolysis of nitrile, 133 (obtained by alkylation of diphenylacetonitrile with the morpholine analog of the chloro-amine used in the original preparation of methadone), affords acid, 134. Conversion to the acid chloride followed by reaction with pyrrolidine affords racemoramide (135) Separation of the (+) isomer by optical resolution gives dextromoramide, an analgesic an order of magnitude more potent than methadone. 

Deserpldine, 320, 321 Desimlpramine, 402 Desmethylmorphine, 289 Desulfurization, 130, 166 Dexamethosone, 199 Dexbrompheniramine, 77 Dexchlorpheniramine, 77 Dextroamphetamine, 70 Dextromoramide, 82 Dextromorphan, 293 Dextrothyroxine, 92 Diabetes, 136 Dianlthazole, 327 Diazepam, 365, 366 Diazoxide, 355 Dibenamine, 55 Dibenzepine, 405 Dibucaine, 15 Dicarbocyanine dye, 327 Dichlorisone, 203 Dichloroisoproteronol, 65, 66 Dichlorophenamide, 133 Dicloxacillin, 413 Dicoumarol, 147 Dicyclonine, 36... 

The most known narcotics are the opium alkaloids such as morphine, codeine, thebaine, papaverine, noscapine and their derivatives and modified compounds such as nalmorphine, apomorphine, apomopholcodine, dihydrocodeine, hydro-morphone and heroine, also known as diamorphine. Synthetic narcotics share the structural skeleton of morphine and include dextromethorphan, pentazocine, phenazocine meperidine (pethidine), phentanyl, anfentaitil, remifentalin, methadone, dextropropoxyphene, levoproxyphene, dipipanone, dextromoramide, meptazinol and tramadol. Thebaine derivatives are also modified narcotics and include oxycodone, oxymorphone, etorphine, buprenorphine, nalbuphine, naloxone or naltrexone. Narcotics can be semi-synthesized or totally synthesized from the morphine and thebaine model. The compounds serve various purposes in clinical practise. 

In general, dimethylamino gives optimum activity, but 5- and 6-membered alicyclic basic units also yield strong analgesic compounds (e.g. phenadoxone, dipipanone, dextromoramide)... 

Opioid receptor binding Dextromoramide is a p-selective opioid with a higher receptor affinity than morphine. 

Analgesic efficacy and clinical use Dextromoramide tartrate (Kay, 1973) is a strong opioid related to methadone and is used in the treatment of severe pain (Judd et al., 1981). 

Dosages and routes of administration Dextromoramide is administered orally and rectally. The parenteral potency is in the range of morphine, but the duration of action is shorter. 

Jones, T.E., Morris, R.G., Saccoia, N.C., Thorne, D. Dextromoramide pharmacokinetics following sublingual administration, Palliat. Med. 1996, 10, 313-317. 

Kay, B. A study of strong oral analgesics the relief of postoperative pain using dextromoramide, pentazocine and bezitramide, Br. J. Anaesth. 1973, 45, 623-628. 

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