Hydromorphone structure

Structurally, hydromorphone is similar to morphine and has similar painkilling and other effects in the body. Hydromorphone by weight is actually a stronger painkiller than morphine. Hydromorphone is combined... 

Figure 7.16. C-ring derivatives of morphine. Structures of hydromorphone (5) and oxycodone (6) from Fig. 7.1 are included for comparison. Nalmefene (64) is an antagonist, TRK-820 (65) is a K-selective agonist, and nalbuphine (66) is a mixed agonist/antagonist.

C-3 phenolic hydroxyl C-6 allylic alcohol and C = C between C-7 and C-8 as depicted in the following stmcture(s). It is, however, pertinent to mention here that several synthesized structural analogues even before 1930 are still constituted as vital and potential drugs in the therapeutic armamentarium, for instance codeine ethyl morphine (Dionin ) diacetyl morphine (heroin) hydromorphone... 

The best 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, hydromorphone, and heroin, also known as diamorphine. Synthetic narcotics share the structural skeleton of morphine and include dextromethorphan, pentazocine, phenazocine meperidine (pethidine), phentanyl, anfentanil, remifentalin, methadone, dextropropox3q)hene, levoproxyphene, dipipanone, dextromoramide, meptazinol, and tramadol. Thebaine derivatives are also modified narcotics and include oxycodone, oxymorphone. 

As shown in Figure 8, the total stabilization energy of the model hydration of hydromorphone base is 4.1 kcal mole compared to 9.4 kcal mole for oxymorphone base, with similar energies for hydrocodone and oxycodone. Since the models in Figure 7 are considered to represent the hydration of the fragments by which the two molecules differ structurally, this result indicates that the free base of oxymorphone... 

Opioids can be classified according to stractural similarity with morphine in semisynthetic and synthetic derivatives. Structurally similar, semisynthetic morphinelike derivatives as well as stracturally distinct opioids have been synthesized to search for compounds able to improve analgesic effects that minimize side effects. Semisynthetic derivatives include morphine-related agonists (hydromorphone, hydrocodone, oxycodone, oxymorphone, and codeine), and moiphine-related partial agonist and antagonists (buprenorphine, naloxone, and naltrexone). Synthetic derivatives include phenylpiperidines (meperidine and loperamide), diphenylpropylamines (methadone and propoxyphene), and piperidines (fentaityl, alfentanyl, sufentanil, and remifen-tanil) (Dumas and Pollack, 2008). 

Now, concerning the morphine identification itself, we ll point out that one means to achieve it is to treat it with hexacyanoferrate(III) and Fe +. According to some works, a free radical reaction involving dioxygen may occur. Then a semiquinone radical may form, and the latter may duplicate into pseudomorphine, which may give a blue color with FeCls. Hydromorphone, whose structure is close to that of morphine and that also possesses a phenol function, gives a blue color with FeCls. The color... 

For example, hydromorphone (brand name Dilaudid) is hydrophilic (like lidocaine and cocaine, it has a readily protonatable nitrogen and, in fact, is generally administered as the hydrochloride salt). This analgesic, the structure of which is shown in Figure 4.5, has a... 

Figure 4.5. Structure of hydromorphone, an opioid narcotic. Nearly all opioids bind the p-oplold receptor. There Is no physiological or clinical difference between legal opioids, such as morphine, and illegal ones, such as heroin. In fact, heroin wes thought to be a nonaddic-tive analogue of morphine when it was first developed.

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