Apomorphine Alcohol

Here the alcoholic hydroxyl is first protonated and then eliminated as water. The allylcarbenium ion (2) is initially stabilized by elimination of the proton at C-14. Then the ether link is opened after protonation of the ring oxygen with the formation of carbenium ion (3), whereby the neighboring C-C bond of the piperidine ring is cleaved with aromatization of the C ring. The carbenium ion (4) formed is stabilized by elimination of a proton and ring closure to apomorphine (5). 

Apomorphine hydrochloride (Figure 44.2), an alkaloid obtained in the laboratory by rearrangements within the morphine molecule, is a grayish-white, glistening, light-sensitive, and air-sensitive crystalline powder, soluble in both water and alcohol in the proportions of about 1 50 it is available in small amounts in bulk and more easily as 5 mg (1/12 grain) tablets. 

Emetics, when administered in small doses, act as expectorants and are used in inflammatory conditions of the respiratory tract to increase the bronchial secretion and render it less tenacious. The most commonly used expectorants are ipecac, ammonium chloride, and apomorphine. The last named is administered in doses of 1 mg in the form of an elixir or syrup. Apomorphine injected in subemetic doses of 1 to 2 mg is also used as a sedative in the delirium following anesthesia, in acute alcoholic psychosis, and in patients manifesting severe agitation prior to anesthesia. 

The most sensitive test for apomorphine is that described by Grim-bert and Leclere [33] as follows a solution of a salt of the base is boiled for a few seconds with five drops of saturated mercuric chloride solution and five drops of 10 per cent, sodium acetate and the solution extracted with amyl alcohol, which is coloured blue (sensitive to 1 part in 800,000 [34]). 

Demethylation of morphothebaine can be effected by heating with dilute hydrobromic acid at 170° C., the product being 6-hydroxyapo-morphine, which reduces silver nitrate very rapidly and is oxidized by atmospheric oxygen even more readily than apomorphine [16]. Morphothebaine and its dimethyl ether give dark green amorphous substances on oxidation with alcoholic iodine [5],... 

Ipecac is a mixture of the alcohol-soluble alkaloid that is obtained from the South American plant Cephaelis ipecacuanha and is used solely in the form of syrup of ipecac. Apomorphine hydrochloride and copper sulfate are also emetics. Syrup of ipecac and copper sulfate cause emesis by locally irritating the stomach, whereas apomorphine stimulates the chemoreceptor trigger zone for emesis located in the caudal portion of the fourth ventricle (area postrema), which in turn stimulates the vomiting center in the lateral reticular formation of the medulla (see also Figure 73). 

Ipecac is a mixture of the alcohol-soluble alkaloid which is obtained from the South American plant Cephaelis ipecacuanha, and is used solely in the form of syrup of ipecac. Apomorphine hydrochloride and copper sulfate are also emetics. 

Statements on the possibility of tolerance to the emetic effect of apomorphine are conflicting. Addiction to it seems never to have been reported. Apomorphine has been recommended as a hypnotic in alcoholic delirium. Narcosis caused by morphine seemed to be reenforced Avith apomorphine (1). 

The hypotensive adverse effects of apomorphine may possibly be increased by alcohol. The concurrent use of other drugs used for erectile dysfunction or dopamine agonists or antagonists is not recommended. However, domperidone, and prochlorperazine are said not to interact when apomorphine is used for erectile dysfunction, and domperidone is the recommended antiemetic when apomorphine is used for Parkinson s disease. There is evidence that antidepressants, antiepileptics, and ondansetron do not interact adversely. 

The manufacturers say that interaction studies in subjects given apomorphine (for erectile dysfunction) found that alcohol increased the incidence and extent of hypotension (one of the adverse effects of apomorphine). They also point out that alcohol can diminish sexual performance. ... 

Dent, J. Y. Brit.J. of Addiction to Alcohol Other Drugs, 46,1949, 15-28. (Apomorphine treatment of addiction)... 

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