Scopoletin

Other Names Hyoscin, (-)-hyoscin, hyoscine, hyoszin, L6(-),7epoxytropin- tropate, I-hyoscine, scopolamin, [7(S)( la,213,413,5a,713)] -a-(hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo- [3.3.1.02,4] non-7-ylester, skopolamin, tropane acid ester of skopolin Substance type: tropane alkaloid Scopolamine was first isolated in 1888 by E. Schmidt from the roots of (( Scopolia atropoides" (= Scopolia carniolica). It is very closely related to atropine and is a characteristic component of plants from the Nightshade Family (Solanaceae), especially the psychoactive species. For the pharmaceutical industry, the most important sources of scopolamine are the Australian duboisias (Duboisia spp.), the dried leaves of which can contain up to 70/0 alkaloids. Scopolamine is also produced by the recrystallization of hyoscyamine. For medicinal purposes, scopolamine is administered at dosages of 0.5 to 1 mg, with a total daily maximum dosage of 3 mg. The lowest lethal dosage for humans is about 14 mg (Roth et a1. 1994:921*). Scopolamine is a very potent hallucinogen that Leuner (1981 *) classified as a "Class II" hallucinogen because of its simultaneously hallucinogenic and narcotic/consciousness-clouding effects (cf. also Dittrich 1996*). According to Hunnius, scopolamine is utilized in medicine as a hypnotic agent, especially for cases of "agitated states in the mentally ill, for Parkinson's and paralysis agitans, and for treating withdrawal of morphine users" (Hunnius 1975, 609*). In contrast to atropine, which initially stimu1ates the central nervous system, scopolamine induces predominantly a narcotic paralysis from the beginning, which is why it serves as a "chemical straitjacket" for agitated mental patients. Delirium and hallucinations are not infrequently seen ... with therapeutic application. . . . Chronic scopolamine poisoning with gradually increasing dosages leads to psychoses with hallucinations. (Fiihner 1943, 202 f.*) In the former East Germany, scopolamine was still being used as a "chemical straightjacket" in the 1980s (Ludwig 1982, 148*; Schwarz 1984). Scopolamine may be combined with morphine for the same purpose (Rompp 1950, 264*). A combination of scopolamine hydrobromide and morphine hydrochloride is used as a preoperative anesthesia (cf. soporific sponge). Recent tests with mice found that scopolamine hydrobromide causes a marked increase in anxiety as compared to scopolamine methylbromide (Rodgers and Cole 1995). To treat motion sickness-a use to which scopolamine has long been put (Rompp 1950, 265*)-an adhesive patch was developed that contains 1.5 mg scopolamine and can be adhered behind the ear as needed. The active component is absorbed through the skin into the blood vessels of the ear region and affects the organs of balance in the ear. This property of scopolamine supports the idea that the constituents found in witches' ointments could be absorbed when the mixtures were rubbed onto the skin. Scopolamine was a popular inebriant in the Munich jazz scene of the 1950s. Because the dosages used were often so high, many of the concerts had to end early.

Plants CQl1tail1ing. Scop.olall1ine (from Festi1995*;Hagemann et a1. 1992; Ripperger 1995; supplemented) <tbody> </tbody> LORANTHACEAE Benthamia alyxifolia leaves SOLANACEAE   Anthoceris ilicifolia Hook. root Atropa belladonna (L-scopolamine) root Atropanthe sinensis (Hems1.) Pascher fruits, root Brugmansia (all species) entire plant Datura stramonium entire plant Daturaspp. entire plant Duboisia hopwoodii leaves Duboisia spp. leaves, bark Hyoscyamus niger entire plant Hyoscyamus spp. entire plant Iochroma fuchsioides leaves Iochroma spp. ? Latua pubiflora entire plant Lycium barbarum 1. [syn. Lycium halimifolium Mil1.] entire plant Mandragora officinarum root Mandragora chinghaiensis Kuang et Lu (cf. Mandragora spp.) root Scopolia carniolica (= Scopolia atropoides) root Solandra spp. entire plant Commercial Forms and Regulations The alkaloid is available as scopolamine hydrobromide and scopolamine hydrochloride. Pharmacies usually carry these substances in the form of small flasks for use in injections. Scopolamine requires a prescription. Literature See also the entries for Atropa belladonna, cocaine, and tropane alkaloids. Flicker, C., M. Serby, and S. H. Ferris. 1990. Scopolamine effects on memory, language, visuospatial praxis and psychomotor speed" Psychopharmacology 100:243-50. Hagemann, K., K. Piek, J. StOckigt, and E. W. Weiler. 1992. Monoclonal antibody-based enzyme immunoessay for the quantitative determination of the tropane alkaloid, scopolamine. Planta Medica 58:68-72. Heimann, Hans. 1952. Die Skopolaminwirkung. Basel and New York: S. Karger. Keeler, M. H., and F. J. Kane. 1968. The use of hyoscyamine as a hallucinogen and intoxicant. American Journal ofPsychiatry 124:852-54. Ripperger, Helmut. 1995. (5)-scopolamine and (5)norscopolamine from Atropanthe sinensis. Planta Medica 61:292-93. Rodgers, R. J., and J. C. Cole. 1995. Effects of scopolamine and its quaternary analogue in the murine elevated plus-maze test of anxiety. Behavioral Pharmacology 6:283-89. Schwarz, H.-D. 1984. Hyoscin (= Scolpolamin) statt Zwangsjacke. Zeitschrift fur Phytotherapie 5 (3): 840-41.