Hyoscine Alcohol

These investigations have followed three main lines, (1) alterations in the amino-alcohol nucleus, (2) variation in the alkyl or acyl side-chains, (3) influence of stereoisomerism. Tropine and ecgonine, the basic components of atropine and cocaine, lend themselves to such investigations, but scopine, the amino-alcohol of hyoscine is so labile that systematic modification of this alkaloid has not yet been possible. 

The hyoscine system occurs alone in certain northern Duboisia myo-poroides, and forms scopine, -tropine, dihydroxytropane and, in Datura meieloides, teloidine. Of these amino-alcohols, all the scopine is esterified by tropic acid and the minor bases by tiglic, methylbutyric or isovaleric acid, which contain the isoprene skeleton and are presumed to arise from that source. 

The alcohol portion in hyoscyamine is tropine in hyoscine it is the epoxide scopine. Tropine is an example of an azabicyclo[3,2,l]octane system with a nitrogen bridge, whereas scopine is a tricylic system with a three-membered epoxide ring fused onto tropine. Note that systematic nomenclature considers an all-carbon ring system with one carbon replaced by nitrogen hence, tropane is an azabicyclooctane (see Section 1.4). 

Until the mid-19th century such surgery as was possible had to be undertaken at tremendous speed. Surgeons did their best for terrified patients by using alcohol, opium, hyoscine, or cannabis. With the introduction of general anaesthesia, surgeons... 

Datura metel is probably the most readily available source of hyoscine. The powdered drug is extracted with hot alcohol and the crude alkaloids are isolated in the same way as has been described under hyoscyamine, except that sodium bicarbonate is employed, instead of ammonia, for liberating the bases. The alkaloid is neutralised exactly with hydrobromic acid and the solution of the hydrobromide concentrated. The salt which crystallises out on cooling is separated and purified by recrystallisation from water, until of constant melting point. 

Subsequently, Chan reported on twenty-four cases of overdose of a product containing valerian dry extract 75 mg, hyoscine hydrobromide 0.25 mg, and cyproheptadine hydrochloride 2 mg. Six patients developed vomiting, and fifteen underwent gastric lavage. Co-ingestants included alcohol (n = 10), cold products n = 3), hypnotics (n = 2), unknown drugs (n = 2), and gasoline (n = 1). Symptoms were mainly central nervous system depression and anticholin-... 

When Z-scopolamine (Z-hyoscine) is warmed with barium hydroxide (52, 56, 232), dilute alkalies (232), or acids (60, 212) it is hydrolyzed to tropic acid and a new base (CsHisOjN), scopoline (oscine). Depending on the conditions of the experiment, the tropic acid recovered may be either the pure Z-form or the partially racemized acid, or may even be dehydrated to atropic acid (52, 64, 232). The scopoline isolated from these experiments is invariably optically inactive (212). By analogy with Z-hyoscyamine, Z-scopolamine would appear to be a base (scopoline) in which the alcoholic... 

Propantheline appears not to affect blood-alcohol levels, whereas atropine may cause a modest reduction. Marked impairment of attention can occur if alcohol is taken in the presence of atropine or glycopyrronium (glycopyrroiate), probabiy making driving more hazardous. No adverse interaction usuaiiy appears to occur with transdermal hyoscine and aicohoi. 

A double-blind crossover study in 12 healthy subjects found that a transdermal hyoscine preparation (Scopoderm-TTS) did not alter the effects of alcohol on the performance of several psychometric tests (Critical Flicker Fusion Frequency, Choice Reaction Tasks), nor was the clearance of alcohol or hyoscine changed. Blood-alcohol levels of up to 80 mg%, and 130 mg%, were studied. Nevertheless, the manufacturer suggests... 

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