Dihydrocodeinone

Dihydrocodeine [125-28-0] (33), introduced in Germany before 1930, and dihydrocodeinone enol acetate [466-90-0] (34) both have clinical activity and addiction potential comparable to codeine. 

Dihydromorphinone, Cj,Hjg03N, and derivatives. Dihydromorphinone (LIII MeO HO) is formed when morphine in solution is treated with relatively large quantities of platinum or palladium catalyst under various conditions.It melts at 262-3° and yields an oxime, m.p. > 234°. The hydrochloride is the drug known as dilaudid. On 0-methyla-tion dihydromorphinone yields dihydrocodeinone (see above), and when dissolved in ether and treated with methyllithium the corresponding tertiary alcohol, 6-methyldihydromorphine, CigHggOgN, m.p. 209-211°, Wd ° 14i7° (EtOH), is formed. This on methylation with diazomethane gives 6-methyldihydrocodeine as described above (Small and Rapoport... 

Since dihydrothebainone is also formed by hydrogenation of thebainone (Schopf and Hirsch i), and as Schopf and Pfeifer have shown that 1 5-dibromodihydrothebainone, on treatment with alkali, is converted into. 1-bromodihydrocodeinone by formation-of the C -C oxygen bridge, and this, on catalytic hydrogenation, yields dihydrocodeinone (LIII, p. 246), the constitution of which has been demonstrated by Schopf (p. 244), there can be little doubt that dihydrothebainone is represented by (LI). Schopf and Winterhalder have also isolated as an oxime (m.p. 228°, [a] °° — 115-8°) an e.pidihydrothebainone, which is regarded as the epimeride of dihydrothebainone. 

Numerous derivati es of morphine have been devised for use in medicine including acyl derivatives, of which diacetylmorphine (C], Hj,03N, Ac2, m.p. 173°, [a]J°° — 166° (MeOH) B. HCl. 2H2O, m.p. 231-2°) is the best known, alkyl and other ethers such as the ethyl-and benzyl-morphines, dihydro- and dihydroketo-compounds such as dihydromorphine, dihydrocodeine, dihydromorphinone, dihydrocodeinone and hydroxydihydrocodcinone, and the deoxy-compounds, e.g., dihydro-deoxymorphine and methyldihydrodeoxymorphine. 

Dihydrocinchonicine, 452 Dihydrocinchonidine, 429 Dihydrocinchonine, 428 Dihydrocinchotoxine, 452 Dihydrocodeine, 260 Dihydrocodeinone, 245, 260, 270 Dihydroeodeinone oxime, reactions, 244 Dihydromeiacodeinone, 249 Dihydrocryptopine and isodihydrocryptopine, 296 Dihydrocupreicine, 452 Dihydrocupreidine, 431 Dihydrocupreine, 431 Dihydrodeoxymorphines, 254, 260-2 Dihydroecgonidine, 99 Dihydro- -erythroidines, 387... 

Rice, K.C. (1980) Synthetic Opium Alkaloids and Derivatives. A Short Total Synthesis of (ib)-Dihydrothebainone, ( )-Dihydrocodeinone, and ( )-Nordihydrocodemone as an Approach to a Practical Synthesis of Morphine, Codeine, and Congeners. Journal of Organic Chemistry, 45, 3135-3137. 

Hong, C.Y, Kado, N., Overman, L.E. (1993) Asymmetric Synthesis of Either Enantiomer of Opium Alkaloids and Morphinans. Total Synthesis of (—)- and (-f)-Dihydrocodeinone and (—)- and (-F)-Morphine. Journal of the American Chemical Society, 115, 11028-11029. 

Parker, K.A. Fokas, D. (2006) Enantioselective Synthesis of (—)-Dihydrocodeinone A Short Formal Synthesis of (—)-Morphine. Journal of Organic Chemistry, 71,449 55. 

The inifial sfeps in fhe mefabolism of morphine and codeine by Pseudomonas putida MIO involve oxidafion of fhe C-6 hydroxy group and subsequenf reducfion of fhe 7,8-olefinic bond, forming hydromorphone (dihydromorphinone) and hydrocodone (dihydrocodeinone), respectively (Scheme 4) [52], These products have important industrial appUcations hydromorphone is an analgesic some seven times more potent than morphine [53],... 

How many grains of dihydrocodeinone should be used in compounding the prescription ... 

Dihydrocodeinone gr 1/12/tsp Hydriodic Acid Syrup Cherry Syrup aa ftiii Sig. Tsp. every 2 hr. for cough... 

Dihydromorphinone is 3-4 times more powerful than morphine and dihydrocodeinone is just a little less than morphine in potency. Their pitfall is an addiction liability, as great if not greater than morphine. To produce Hydrogenate morphine or codeine in a warm, strongly acidic solution, in a large excess of palladium or platinum catalyst, as per instructed in the reductions chapter. 

Codeine. Is a narcotic derived from morphine and is addictive. It can be purchased over the counter, but you will have to sign for it. Sometimes you will have to show identification. It creates feelings of euphoria and weightlessness with doses of about 50 to 150 mg. It can also be made much more potent by hydrogenating to dihydrocodeinone as instructed in the analgesic chapter in this book. 

Dexivacaine, 95 DBxnorgBstrel acetime, 152 Diabetes, 116 Diamocaine, 336 Diapamide, 93 Diaveridine, 302 Diazepam, 452 Diazoxide, 395 Dibenzepin, 424, 471 DichloroisopTTOterenol, 106 Diclofenac, 70 Dicyanamide, 21 Dieckmann cyclization, 72 Difenoximide, 331 Difenoxin, 331 Diflucortolone, 192 Diflumidone, 98 Diflunisal, 85, 86 Difluoromethylene groups, from ketones, 196 Difluprednate, 191 Dihydrocodeinone, 318 Dihydropyridine synthesis, 283... 

CNS dihydrocodeinone and oxycodone/alkal. dihydro- morphine from opium/alkal. 

Dihydrocodeinone (hydrocodone in Hycodan, Vicodin, and Lortab) not to exceed 300 mg/dL or 15 mg/tablet... 

The risk of addiction is greater in the case of dihydrocodeinone than with codeine, but small doses (5 to 10 mg) are often of value in tuberculosis, measles, atypical pneumonia, etc., conditions in which cough is a troublesome symptom. 

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