Diacetyl morphine

Diamorphine (3,6-diacetyl morphine, heroin) is a semi-synthetic derivative of morphine. It was first synthesised in 1874 and put on the market in 1898 as a non-habit-forming alternative to morphine ... 

Heroin (diamorphine, diacetyl morphine) is potent and fast-acting, but its use is prohibited in the USA and Canada. In... 

Dole VP, Nyswander M. A medical treatment for diacetyl-morphine (heroin) addiction. A clinical trial with methadone hydrochloride. JAMA 1965 193 646-50. 

Morphine binds with very high affinity to several receptors in the CNS and is a potent analgesic and central depressant. It is also the prototype for many semisynthetic derivatives (e.g., naloxone, oxycodone, ethorphine, nalbuphine, and buprenophine) with various degrees of analgesic and narcotic properties. Heroin is diacetyl morphine. 

Vongerichten reported the isolation, as a by-product in the preparation of 3 4-diacetoxyphenanthrene by heating diacetyl-morphine with silver acetate and acetic anhydride at 180° C., of a /3-morphi-methine that could be methylated to /3-codeimethine methiodide [88], Repetition of this work revealed the product to be a monoacetylated /3-morphimethine that can be methylated and hydrolysed to /3-codeimethine, and reduced to [lxxi, R = Ac] [51]. 

As a classical pre-medicine before operations morphine+scopolamine 10 mg+0.4 mg is used. Morphine is used to make diacetyl-morphine (heroin) and codeine (methyl morphine). 

The chemical structures of morphine and heroin in relation to other closely related opiates such as codeine and dihydrocodeine are shown in Figure 2. Morphine has a "phenolic" -OH group in the 3 position and an aliphatic (alcoholic) -OH group in the 6 position. When both -OH groups (3 and 6 positions) are acetylated, diacetyl morphine, better known as diamorphine or heroin is produced. Codeine is the 3-methyl derivative of morphine by substituting the phenolic -OH group with a methyl group in the... 

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... 

Heroin production Morphine free base is refluxed in acetic anhydride for 5h. The mixture is allowed to cool and is neutralized with sodium carbonate causing the precipitation of crude diacetyl-morphine free base, the illicit drug in heroin samples. Monoacetylation of morphine and acetylation of any codeine present also occurs. The crude product is purified by dissolving in acidified water containing charcoal and the free base precipitated by the addition of sodium carbonate. If the hydrochloride salt is required the free base is dissolved in acetone and the product precipitated by the addition of hydrochloride acid. 

Rapid and Sensitive Gas Chromatographic Determination of Diacetyl-morphine and Its Metabolite Monoace tylmorphine in Blood Using a Nitrogen Detector... 

D. Djozan and T. Baheri, Preparation and evaluation of solid-phase microextraction fibers based on monolithic molecularly imprinted polymers for selective extraction of diacetyl-morphine and analogous compounds, / Chromatogr. A, 1166 (1-2) 16-23,2007. 

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