Atropine Alcohol

Atropine causes dilation of the pupil of the eye. A drop or two of an aqueous solution, containing 1 part in 130,000 parts of water, introduced into the eye of a cat is sufficient to produce this effect. When warmed with sulphuric acid and a small crystal of potassium dichromate, atropine develops a bitter almond odour. Evaporated to dryness on a water-bath with concentrated nitric acid, it gives a residue which becomes violet on adding a drop of sodium hydroxide solution in alcohol (Vitali s test). With a solution of mercuric chloride atropine gives a yellow to red precipitate of mercuric oxide. 

Hyoscyamine is readily converted into the dZ-form, atropine, by melting or by the addition of small quantities of caustic alkali to its cold alcoholic solution. The same change is brought about by sodium carbonate or ammonia. ... 

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. 

Reduction of tropanone affords the alcohol epitropanol (13), epimeric with the alcohol obtained on hydrolysis of atropine. 

Esters of diphenylacetic acids with derivatives of ethanol-amine show mainly the antispasmodic component of the atropine complex of biologic activities. As such they find use in treatment of the resolution of various spastic conditions such as, for example, gastrointestinal spasms. The prototype in this series, adiphenine (47), is obtained by treatment of diphenyl acetyl chloride with diethylaminoethanol. A somewhat more complex basic side chain is accessible by an interesting rearrangement. Reductive amination of furfural (42) results in reduction of the heterocyclic ring as well and formation of the aminomethyltetrahydro-furan (43). Treatment of this ether with hydrogen bromide in acetic acid leads to the hydroxypiperidine (45), possibly by the intermediacy of a carbonium ion such as 44. Acylation of the alcohol with diphenylacetyl chloride gives piperidolate (46). ... 

There is an increased central nervous system (CNS) depressant effect when the skeletal muscle relaxants are administered with other CNS depressants, such as alcohol, antihistamines, opiates, and sedatives. There is an additive anticholinergic effect when cyclobenzaprine is administered with other drugs with anticholinergic effects (eg, antihistamines, antidepressants, atropine, haloperidol). See Chapter 30 for information on diazepam. 

Gastrointestinal Anticholinergic Combinations Antrocol Elixir—atropine sulfate, phenobarbital, alcohol Barbidonna—atropine, scopolamine HBr, hyoseyamine sulfate, phenobarbital... 

Bellacane Elixir—atropine, scopolamine HBr, hyoseyamine HBr or sulfate, phenobarbital, alcohol, tartrazine Bellacane SR Tablets—1-alkaloids of belladonna, phenobarbital, ergotamine tartrate Bellergal-S Tablets—1-alkaloids of belladonna, phenobarbital, ergotamine tartrate Butibel Elixir—belladonna extract, butabarbital sodium, alcohol, sucrose, saccharin Butibel Tablets—belladonna extract, butabarbitol Chardonna-2 Tablets—belladonna extract, phenobarbital Donnatal Elixir—atropine, scopolamine HBr, hyoseyamine HBr or sulfate, phenobarbital, alcohol, sucrose, saccharin... 

Seeking alcohol, the victims had broken into the prison pharmacy, where they found a bottle of clear fluid that appeared to be just what they were seeking. Eagerly, they downed the contents. Unfortunately, the tincture was not merely alcohol, but contained a hefty dose of atropine. An hour later, two of them were... 

The Mannich reaction was used for the first synthesis of tropine, the parent alcohol of the tropane alkaloids. One of the natural tropane alkaloids used medicinally is hyoscyamine, sometimes in its racemic form atropine. Hyoscyamine is an anticholinergic, competing with acetylcholine for the muscarinic site of the parasympathetic nervous system, and thus prevendng the passage of nerve impulses. 

Concomitant conditions Use with caution in the following patients exposed to extreme heat or phosphorus insecticides atropine or related drugs because of additive anticholinergic effects those in a state of alcohol withdrawal those with dermatoses or other allergic reactions to phenothiazine derivatives because of the possibility of cross-sensitivity those who have exhibited idiosyncrasy to other centrally acting drugs. 

The best known of the muscarinic blocking drugs are the belladonna alkaloids, atropine (Atropine) and scopolamine (Scopolamine). They are tertiary amines that contain an ester linkage. Atropine is a racemic mixture of DL-hyoscyamine, of which only the levorotatory isomer is pharmacologically active. Atropine and scopolamine are parent compounds for several semisynthetic derivatives, and some synthetic compounds with little structural similarity to the belladonna alkaloids are also in use. All of the antimuscarinic compounds are amino alcohol esters with a tertiary amine or quaternary ammonium group. 

Each 5 mL (teaspoonful) of elixir (23% alcohol) contains phenobarbital 16.2 mg, hyoscyamine sulfate 0.1037 mg, atropine sulfate 0.0194 mg, and scopolamine hydrobro-... 

Noncarcinogens atropine, benzyl alcohol, benzyl isothiocyanate, benzyl N=34 thiocyanate, biphenyl, d-carvone, codeine, deserpidine,... 

Diphenoxylate Hydrochloride. l-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylic acid monohydrochlorhydrate [3810-80-8] (Lomotil) (13) is a white, ododess, crystalline powder that melts at 220—226°C. It is soluble in methanol, sparingly soluble in ethanol and acetone, slightly soluble in water and isopropyl alcohol, freely soluble in chloroform, and practically insoluble in ether and hexane. The method of preparation for diphenoxylate hydrochloride is available (11). Diphenoxylate hydrochloride [3810-80-8] (13) is an antidiarrheal that acts through an opiate receptor. It has effects both on propulsive motility and intestinal secretion. Commercial forms are mixed with atropine to discourage abuse. 

Atropina Atropine, C17H23N03, white, acicular crystals, odorless, of bitter taste and alkaline reaction very soluble in alcohol and in chloroform, also soluble in 130 of water at 59°F. It is decomposed by prolonged contact with caustic alkalies and is resolvable into tropine and tropic acid. 

Atropinae Sulphas Atropine sulfate, (C17H23N03)2H2S04, a white powder with a bitter taste and neutral reaction, soluble in 0.4 of water and 6.2 of alcohol at 59°F. 

Oleatum Atropinae Oleate of atropine, a 2% solution of the alkaloid in alcohol 2, oleic acid 50, and olive oil to 100. 

As a gastric secretagogue, alcohol stimulates the secretion of gastric juice, which is rich in acid and pepsin. Therefore, the consumption of alcohol is contraindicated in subjects with untreated acid-pepsin disease (Figure 68.2). In addition, alcohol releases histamine, which in turn releases gastric juice. This effect is not blocked by atropine. 

THC has a variety of pharmacologic effects that resemble those of amphetamines, LSD, alcohol, sedatives, atropine, and morphine. Important opioid interactions include reduction in opioid dependence in CB1 knockout mice lacking the CB1 receptor. 

Atropin was obtained from belladonna roots and by racemisation of L-hyoscyamine with dilute alkali or by heating in chloroform solution. The alkaloid was crystallised from alcohol on addition of water, or from chloroform on addition of light petroleum, or from acetone in long prisms, m.p. 118°C, sublimed unchanged when heated rapidly. It is soluble in alcohol or chloroform, less soluble in ether or hot water, sparingly so in cold water (in 450 L at 25°C) and almost insoluble in light petroleum. Atropine is optically inactive. 

---