Tropane alkaloids scopolamine

These are the group of alkaloids that possess a 8-methyl-8-aza-hicyclo [l,2,3]octane or tropane skeleton, e.g. atropine, cocaine and scopolamine. Tropane alkaloids occur mainly in plants from the families Solanaceae and Erythroxylaceae. 8-Aza-hicyclo[l,2,3]octane, i.e. tropane without the 8-methyl group, is known as nortropane. 

Artificial polyploidy bioreactor hairy roots hyoscyamine plant cell cultures scopolamine tropane alkaloids biosynthesis... 

Biosynthesis of tropan alkaloids hyosciamine and scopolamine by isomerization of alkaloid littorine in Datura. stramonium and related species 98CSR207. 

It has been confirmed that isoleucine but not 3-hydroxy-2-methylbutanoic acid is a precursor for the tiglic acid which is the esterifying acid in some tropane alkaloids [e.g., meteloidine (77) (735)]. In the biosynthesis of meteloidine (77) from 3a-hydroxytropane (1), the hydroxyl groups at C-6 and C-7 are most probably introduced after esterification at C-3 (5) (Scheme 23). In this connection we would point out that scopolamine (89) is a well-known 2,3) metabolite of hyoscyamine (27) and that the reaction proceeds via 6-hydroxyhyoscyamine [(—)-anisodamine (63)] and 6,7-dehydrohyoscyamine (211) (Scheme 26). 

S. Wada, T. Yoshimitsu, N. Koga, H. Yamada, K. Oguri, H. Yoshimura, Metabohsm in vivo of the Tropane Alkaloid, Scopolamine, in Several Mammaban Species , Xenobiotica 1991, 21, 1289-1300. 

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... 

Synthesis of scopolamine (Fig. 4), a tropane alkaloid of known anticholinergic properties, was induced hy fivefold in hairy root cultures of Atropa belladonna overexpressing hyoscianine 6[3-hydroxilase. ... 

A. Alkaloids 1. Belladonna-type solanaceous tropane alkaloids [Atropine (1), (—)-Hyoscyamine (2), Scopolamine ((—)-Hysoscine)(3)] Atropa belladonna L. (belladonna), Datura metel L., D. stramonium L. (jimson weed), Hyoscyamus niger L. (henbane), Mandragora officinarum L. (European mandrake), and other solanaceous species Anticholinergics (parasympatholytics)... 

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 tropane alkaloids, especially hyoscine (scopolamine) (18), have been used to treat PD since they increase DA activity by antagonizing cholinergic activity at the muscarinic receptors in the striatum. The naturally occurring alkaloids, foimd in various genera of the Solanaceae, are not... 

Tropane alkaloids Tropane Atropine Cocaine Hyoscyamine Scopolamine/ hyoscine... 

Plants containing indoleamines include Psilocybe mushrooms, morning glory and Virola. Plants containing tropane alkaloids such as the muscarinic antagonists scopolamine and atropine are found in some members of the Solanaceae plant family—including datura, mandrake, henbane and... 

Belladonna contains tropane alkaloids, atropine, hyoscamine, and scopolamine, all... 

Proton61 and carbon-1362 n.m.r. spectroscopy have recently been used extensively for the analysis of tropane alkaloids. The non-equivalence of H-6 and H-7 on the one hand and of H-2 and H-4 on the other in atropine and scopolamine is due to the non-symmetrical shielding by the tropic acid moiety. The configuration of A-substituents, e.g. N-oxides, has been determined by studying the deshielding of the 6- and 7/3-hydrogens. All of these results should be useful for the identification of new tropane alkaloids and other related systems in the future. 

Fig. 7 Selected biotransformation products of diverse tropane alkaloids identified by LC-MS/MS approaches. Depicted metabolites are only an exert of those presented by Chen et al. for anisodamine (Ada) [6], atropine (Atr) [51], and scopolamine (Sep) [7] as well as by He et al. for benztropine (Benz) [59]. Structures were identified from in vivo and in vitro samples following diverse modes of MS/MS analysis as discussed in the section Biotransformation studies...

Incidental and accidental intake of atropine and scopolamine, which are the main tropane alkaloids in plants of the solanecae family, may provoke poisoning of man and livestock [11,13-15, 55, 57,119-122] causing agitation, aggression, hallucinations, dry mouth and skin, mydriasis, loss of consciousness followed by coma combined with tachycardia, hypotension, and hyperthermia [57, 121], A detailed statistical analysis of paediatric plant exposures in Germany within the years 1998-2004 has been provided by Pietsch et al. [123], They found that most prevalent victims of accidental plant exposures are children in the age of 1-6 years presumably being misled by the attractive plump berries. 

Tropane Alkaloids.—It is known that tropine (26) is a precursor for meteloidine (27),42 and its close relative hyoscyamine (29) is a precursor for scopolamine (28).43 Experiments with samples of (26) labelled with /3-tritium at C-6 and C-7 show that entry of the two /S-hydroxy-groups in (27) must occur with normal retention of configuration since almost complete loss of tritium occurred.44 Tritium was again lost almost completely on formation of scopolamine (28). On the assumption that early conclusions45 on the sequential intermediacy of (30) and (31) in the biosynthesis of (28) are correct, formation of (30) involves normal retention of configuration (loss of half the tritium) and cis-dehydration then occurs to give (31) (loss of remaining tritium). [In these experiments the hyoscyamine (29) isolated showed appropriately no loss of tritium.]44... 

Simple Pyrrolidine Alkaloids.—It is well established that ornithine (1) is a key precursor in the biosynthesis of pyrrolidine alkaloids. Notably, the amino-acid (1) is utilized for the biosynthesis of nicotine (5) via the symmetrical intermediate putrescine (3), whereas the biosynthesis of tropane alkaloids, e.g. scopolamine (6), avoids any symmetrical intermediate1,2 (cf. Vol. 11. p. 1). 

The biosynthetic pathway to both nicotine (5) and the tropane alkaloids includes A-methylputrescine (4) as a probable intermediate. New results6 obtained for nicotine (5) and scopolamine (6) with 1 l-13C,14C wef/zy/awmo-15Nl-A-methyl putrescine 1(4) labels as shown nicely confirm this. The specific incorporation of both stable isotopes was closely similar to that of the 14C label in both alkaloids, indicating intact incorporation of the precursor. The labelling patterns deduced are illustrated ( = 13C, = 15N), and they are in accord with earlier results that were... 

---