Datura stramonium Atropine

Hyoscyamine, present in Datura stramonium Atropine, present in Atropa belladonna Cocaine, present in Erythroxylon coca Codeine and morphine, present in Papaver somniferum Terpenoids (come from semiterpene oligomerization) Azadirachtin, present in seeds of Azadirachta indica (neem) Artemisinin, present in Artemisia annua Tetrahydrocannabinol, present in Cannabis sativa Steroids (terpenes with a particular ring structure) Glycosides (heavily modified sugar molecules)... 

Hiom ple Datura stramonium Atropine, scopolamine Smoke or tea as tobacco substitute or hallucinogen Strong hallucinogen... 

At this writing anticholinergic agents are not widely used for the symptomatic treatment of asthma, although compounds such as atropine [51 -55-8] C17H23NO3, (18) have been used for centuries (111). Inhalation of the smoke produced by burning herbal mixtures, such as Datura Stramonium provided bronchodilation and rehef from some of the symptoms of asthma. The major active component in these preparations was atropine or other closely related alkaloids (qv). 

The cholinergic hallucinogens all have common chemical constituents that are responsible for their pharmacological effects (Robbers et al. 1996). These are the tropane alkaloids hyoscyamine, scopolamine (or hyoscine), and atropine (figure 9.16). It is scopolamine, and not atropine or hyoscyamine, which primarily produces the central and hallucinogenic effects because it is the only one that passes the blood-brain barrier sufficiently. However, all three have peripheral effects. Datura stramonium contains 0.1-0.65% tropane alkaloids, which is principally... 

Other plants of the nightshade family, including Atropa belladonna (deadly nightshade), Hyoscyamus niger (black henbane), and Datura stramonium (Jimson weed), contain atropine-like toxins that are anticholinergic, blocking the muscarinic receptors. An incidence in southern Utah of cattle poisoned on black henbane, with many death losses, was recently reported (Pfister, 2003). Atropine and atropine-like alkaloids are discussed Section 2.2.1.7. 

The tropane alkaloids (—)-hyoscyamine and (—)-hyoscine are found in the toxic plants deadly nightshade (Atropa belladonna) and thornapple (Datura stramonium) and are widely used in medicine. Hyoscyamine, usually in the form of its racemate atropine, is used to dilate the pupil of the eye, and hyoscine is employed to control motion sickness. Both alkaloids are esters of (—)-tropic acid. 

The base-catalysed racemization of the alkaloid (-)-hy oscy amine to ( )-hyoscyamine (atropine) is an example of enolate anion participation. Alkaloids are normally extracted from plants by using base, thus liberating the free alkaloid bases from salt combinations. (—)-Hyoscyamine is found in belladonna Atropa belladonna) and stramonium Datura stramonium) and is used medicinally as an anticholinergic. It competes with acetylcholine for the muscarinic site of the parasympathetic nervous system, thus preventing the passage of nerve impulses. However, with careless extraction using too much base the product isolated is atropine, which has only half the biological activity of (—)-hyoscyamine, since the enantiomer (+)-hyoscyamine is essentially inactive. 

Certain plants of the family Solanaceae, such as Atropa belladonna L., Hyoscyamus niger L., and Datura stramonium L., have been used medicinally for centuries in Europe because they contain tropane-type alkaloids.For example, atropine (1) [a racemic mixture of (+)- and (—)-hyoscyamine (2)] and (-)-hyoscyamine are competitive antagonists at the muscarinic acetylcholine receptor site, leading to antispasmodic and antiallergic effects. Scopolamine [(—)-hyoscine)] (3) is used in a transdermal patch for the prevention of motion sickness. Since these tropane alkaloids penetrate the blood-brain barrier, they also have psychoactive effects. ... 

The oldest drugs of this group are different galena drugs isolated from belladonna (Atropa belladonna), henbane (Hyoscyamus niger), and stramonium (Datura stramonium). They are all obtained from plants that contain the L-hiocyamine and a somewhat lesser qnantity of L-scopolamine. As a mnscarinic receptor blocker, L-hioscyamine is mnch more active that D-hioscyamine on both the periphery as well as on the CNS however, a racemic mixture of D,L-hioscyamine— known better as atropine—is preferred in the majority of medical cases because it is readily available. 

Atropine and scopolamine, the main toxic alkaloids of Datura stramonium and Datura ferox, were detected and quantified using HPLC-ESl-MS both in Datura seeds and in the gastric content of a man whose death was ascribed to a fatal heart attack [100]. 

Atropine and its naturally occurring congeners are tertiary amine alkaloid esters of tropic acid (Figure 8-1). Atropine (hyoscyamine) is found in the plant Atropa belladonna, or deadly nightshade, and in Datura stramonium, also known as jimsonweed (Jamestown weed), sacred Datura, or thorn apple. Scopolamine (hyoscine) occurs in Hyoscyamus niger, or henbane, as the /(-) stereoisomer. Naturally occurring atropine is /(-)-hyoscyamine, but the compound readily racemizes, so the commercial material is racemic d,/-hyoscyamine. The /(-) isomers of both alkaloids are at least 100 times more potent than the d(+) isomers. 

Observation of the use of leaves from Datura stramonium for asthma treatment in India led to the discovery of atropine, a potent competitive inhibitor of acetylcholine at postganglionic muscarinic receptors, as a bronchodilator. Interest in the potential value of antimuscarinic agents increased with demonstration of the importance of the vagus nerves in bronchospastic responses of laboratory animals and by the development of a potent atropine analog that is poorly absorbed after aerosol administration and that is therefore relatively free of systemic atropine-like effects. 

The atropine series contains a number of very closely allied alkaloids of which the chief are atropine, hyoscyamine, and hyoscine (also called scopolamine). They are found in the roots and leaves of many plants of the Solanaceae, notably belladonna (Atropa belladonna), henbane (Hyoscyamus niger), the thorn apple or jimson weed (Datura stramonium), and some members of the Duboisia and Scopolia genera. These plants were used during the Middle Ages as sorcerer s drugs and have been smoked, chewed, or imbibed in the form of decoctions by primitive people for the hallucinations and frenzy they produce (Figure 14.1). 

Note The best-known antimuscarinic or anticholinergic drugs are the belladonna alkaloids. The major drugs in this class are atropine, hyoscyamine, and scopolamine. A number of plants belonging to the potato family (Solanaceae) contain similar alkaloids. Atropa belladonna (deadly nightshade), Hyoscyamus niger (henbane), Datura stramonium (jimsonweed or thorn apple), and several species of Scopolia also contain belladonna alkaloids. 

Esters of tropic acid occur in nature and have a comparatively long history of use as drugs. Atropine (DL hyoscyamlne) and Its optical Isomers, the D and L-hyoscyamlnes, and scopolamine (L-hyoselne) and its optical Isomer, D -hyosclne, have been obtained from such plants as deadly nightshade (Atropa belladonna), jimsonweed (Datura stramonium), henbane (Hyoscyamus nlger), horsenettle (Solanum carollnense). and various species of Scopolla. nie L Isomers of both esters are more potent than the D Isomers. 

Datura stramonium (Jimson weed) is a naturally occurring plant that is ingested to induce hallucinogenic effects. Toxicity after ingestion is due to an atropine-containing alkaloid that is present in all parts of the plant but is particularly concentrated in the seeds. 

Guharoy SR, Barajas M. Atropine intoxication from the ingestion and smoking of jimson weed Datura stramonium). Vet Hum Toxicol 1991 33(6) 588-9. 

Hyoscyamine and/or atropine occur in several plants of the family Solanaceae, such as species of Atropa, Datura, Hyoscyamus, Duboisia, Mandragora and Scopolia (20). In some of these plants e.g. belladonna and scopolia, hyoscyamine is the dominant alkaloid throughout the life cycle of the plant. In Datura stramonium, hyoscyamine is the principal alkaloid at the time of flower-... 

Datura stramonium Jimson weed, devil s weed, Thorn apple. Contains atropine, hyoscine, hyoscyamine. Stramonium tea and cigarettes used to be used for asthma. Dilated pupils, mania, red skin colour (dilated vessels and no sweating) thirst, tachycardia, vomiting, convulsions. 100-125 seeds lethal. Death uncommon. Datura was apparently used in India by poisoners to remove idiots from positions of high rank. 

Atropine. endo-( )-a-< Hydroxy methyl )benzene-acetic acid 8-methyl-8-azabicyclo[3.2.1 oct 3 yl ester, laH,-SaH-tropan 3a-ol (+)-tropate dj-hyoscyamine tropic acid ester with tropine di-tropyl tropate tropine tropate. C17-HjjNOj mo] wt 289.38, C 70.56%, H 8.01%, N 4.84%. O 16.59%. Parasympatholytic alkaloid isolated from Atropa belladonna L, Datura stramonium L, and other Solanaceae. 

Datura stramonium Solanum tuberosum a) a) Extremely small amounts of atropine in tubers. 66... 

Tropane Atropine (48), Scopolamine (49) Atropa belladona Datura stramonium HSV Viral protein glycosylation Non-specific at subtoxic concentration [16, 41]... 

Atropine is the racemic form of the alkaloid /-hyoscyamine. The latter is a common tropane alkaloid found in solanaceous plants, such as belladonna (Atropa belladonna), henbane (Hyoscyamus niger), and the deadly nightshade (Datura stramonium). During extraction, Z-hyoscyamine is readily racemized to atropine, which does not occur naturally in more than traces. 

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