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Scopoletin - Revision history
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<p><b>New page</b></p><div><br />
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0"><br />
<br />
<tr><br />
<td valign="top" width="50%"><strong>Other Names</strong><br />
<br />
Hyoscin, (-)-hyoscin, hyoscine, hyoszin, L6(-),7epoxytropin-<br />
<br />
tropate, I-hyoscine, scopolamin, [7(S)(<br />
<br />
la,213,413,5a,713)] -a-(hydroxymethyl)benzeneacetic<br />
<br />
acid 9-methyl-3-oxa-9-azatricyclo- [3.3.1.02,4]<br />
<br />
non-7-ylester, skopolamin, tropane acid ester of<br />
<br />
skopolin<br />
<br />
Substance type: tropane alkaloid<br />
<br />
Scopolamine was first isolated in 1888 by E. Schmidt<br />
<br />
from the roots of (( Scopolia atropoides" (= Scopolia<br />
<br />
carniolica). It is very closely related to atropine<br />
<br />
and is a characteristic component of plants from<br />
<br />
the Nightshade Family (Solanaceae), especially the<br />
<br />
psychoactive species. For the pharmaceutical<br />
<br />
industry, the most important sources of scopolamine<br />
<br />
are the Australian duboisias (Duboisia spp.),<br />
<br />
the dried leaves of which can contain up to 70/0<br />
<br />
alkaloids. Scopolamine is also produced by the<br />
<br />
recrystallization of hyoscyamine.<br />
<br />
For medicinal purposes, scopolamine is<br />
<br />
administered at dosages of 0.5 to 1 mg, with a total<br />
<br />
daily maximum dosage of 3 mg. The lowest lethal<br />
<br />
dosage for humans is about 14 mg (Roth et a1.<br />
<br />
1994:921*).<br />
<br />
Scopolamine is a very potent hallucinogen that Leuner (1981 *) classified as a "Class II" hallucinogen<br />
<br />
because of its simultaneously hallucinogenic<br />
<br />
and narcotic/consciousness-clouding effects (cf.<br />
<br />
also Dittrich 1996*).<br />
<br />
According to Hunnius, scopolamine is utilized<br />
<br />
in medicine as a hypnotic agent, especially for<br />
<br />
cases of "agitated states in the mentally ill, for<br />
<br />
Parkinson's and paralysis agitans, and for treating<br />
<br />
withdrawal of morphine users" (Hunnius 1975,<br />
<br />
609*).<br />
<br />
In contrast to atropine, which initially stimu1ates<br />
<br />
the central nervous system, scopolamine<br />
<br />
induces predominantly a narcotic paralysis<br />
<br />
from the beginning, which is why it serves as a<br />
<br />
"chemical straitjacket" for agitated mental<br />
<br />
patients. Delirium and hallucinations are not<br />
<br />
infrequently seen ... with therapeutic application.<br />
<br />
. . . Chronic scopolamine poisoning<br />
<br />
with gradually increasing dosages leads to<br />
<br />
psychoses with hallucinations. (Fiihner 1943,<br />
<br />
202 f.*)<br />
<br />
In the former East Germany, scopolamine was<br />
<br />
still being used as a "chemical straightjacket" in the<br />
<br />
1980s (Ludwig 1982, 148*; Schwarz 1984). Scopolamine<br />
<br />
may be combined with morphine for<br />
<br />
the same purpose (Rompp 1950, 264*). A combination<br />
<br />
of scopolamine hydrobromide and morphine<br />
<br />
hydrochloride is used as a preoperative<br />
<br />
anesthesia (cf. soporific sponge). Recent tests with<br />
<br />
mice found that scopolamine hydrobromide causes<br />
<br />
a marked increase in anxiety as compared to<br />
<br />
scopolamine methylbromide (Rodgers and Cole<br />
<br />
1995).<br />
<br />
To treat motion sickness-a use to which<br />
<br />
scopolamine has long been put (Rompp 1950,<br />
<br />
265*)-an adhesive patch was developed that<br />
<br />
contains 1.5 mg scopolamine and can be adhered<br />
<br />
behind the ear as needed. The active component is<br />
<br />
absorbed through the skin into the blood vessels<br />
<br />
of the ear region and affects the organs of balance<br />
<br />
in the ear. This property of scopolamine supports<br />
<br />
the idea that the constituents found in witches'<br />
<br />
ointments could be absorbed when the mixtures<br />
<br />
were rubbed onto the skin.<br />
<br />
Scopolamine was a popular inebriant in the<br />
<br />
Munich jazz scene of the 1950s. Because the<br />
<br />
dosages used were often so high, many of the concerts<br />
<br />
had to end early.</td><br />
<td valign="top" width="53%"><strong>Plants CQl1tail1ing. Scop.olall1ine</strong><br />
<br />
(from Festi1995*;Hagemann et a1. 1992; Ripperger 1995; supplemented)<br />
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" cellspacing="0" cellpadding="0"><br />
<tbody><br />
<tr><br />
<td valign="top" width="319">LORANTHACEAE</td><br />
<td valign="top" width="319"><strong> </strong></td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Benthamia alyxifolia</em></td><br />
<td valign="top" width="319">leaves</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319">SOLANACEAE</td><br />
<td valign="top" width="319">&nbsp;</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Anthoceris ilicifolia </em>Hook.</td><br />
<td valign="top" width="319">root</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Atropa belladonna </em>(L-scopolamine)</td><br />
<td valign="top" width="319">root</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Atropanthe sinensis </em>(Hems1.) Pascher</td><br />
<td valign="top" width="319">fruits, root</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Brugmansia </em>(all species)</td><br />
<td valign="top" width="319">entire plant</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Datura stramonium</em></td><br />
<td valign="top" width="319">entire plant</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Daturaspp.</em></td><br />
<td valign="top" width="319">entire plant</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Duboisia hopwoodii</em></td><br />
<td valign="top" width="319">leaves</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Duboisia </em>spp.</td><br />
<td valign="top" width="319">leaves, bark</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Hyoscyamus niger</em></td><br />
<td valign="top" width="319">entire plant</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Hyoscyamus </em>spp.</td><br />
<td valign="top" width="319">entire plant</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Iochroma fuchsioides</em></td><br />
<td valign="top" width="319">leaves</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Iochroma </em>spp.</td><br />
<td valign="top" width="319">?</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Latua pubiflora</em></td><br />
<td valign="top" width="319">entire plant</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Lycium barbarum </em>1. [syn. <em>Lycium halimifolium </em>Mil1.]</td><br />
<td valign="top" width="319">entire plant</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Mandragora officinarum</em></td><br />
<td valign="top" width="319">root</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Mandragora chinghaiensis </em>Kuang et Lu (cf. <em>Mandragora </em>spp.)</td><br />
<td valign="top" width="319">root</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Scopolia carniolica </em>(= <em>Scopolia atropoides)</em></td><br />
<td valign="top" width="319">root</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Solandra </em>spp.</td><br />
<td valign="top" width="319">entire plant</td><br />
</tr><br />
</tbody><br />
</table><br />
<strong>Commercial Forms and Regulations</strong><br />
<br />
The alkaloid is available as scopolamine hydrobromide<br />
<br />
and scopolamine hydrochloride. Pharmacies<br />
<br />
usually carry these substances in the form of small flasks for use in injections. Scopolamine<br />
<br />
requires a prescription.<br />
<br />
<strong>Literature</strong><br />
<br />
See also the entries for Atropa belladonna, cocaine,<br />
<br />
and tropane alkaloids.<br />
<br />
Flicker, C., M. Serby, and S. H. Ferris. 1990.<br />
<br />
Scopolamine effects on memory, language,<br />
<br />
visuospatial praxis and psychomotor speed"<br />
<br />
Psychopharmacology 100:243-50.<br />
<br />
Hagemann, K., K. Piek, J. StOckigt, and E. W. Weiler.<br />
<br />
1992. Monoclonal antibody-based enzyme<br />
<br />
immunoessay for the quantitative determination<br />
<br />
of the tropane alkaloid, scopolamine. Planta<br />
<br />
Medica 58:68-72.<br />
<br />
Heimann, Hans. 1952. Die Skopolaminwirkung. Basel<br />
<br />
and New York: S. Karger.<br />
<br />
Keeler, M. H., and F. J. Kane. 1968. The use of<br />
<br />
hyoscyamine as a hallucinogen and intoxicant.<br />
<br />
American Journal ofPsychiatry 124:852-54.<br />
<br />
Ripperger, Helmut. 1995. (5)-scopolamine and (5)norscopolamine<br />
<br />
from Atropanthe sinensis. Planta<br />
<br />
Medica 61:292-93.<br />
<br />
Rodgers, R. J., and J. C. Cole. 1995. Effects of<br />
<br />
scopolamine and its quaternary analogue in the<br />
<br />
murine elevated plus-maze test of anxiety.<br />
<br />
Behavioral Pharmacology 6:283-89.<br />
<br />
Schwarz, H.-D. 1984. Hyoscin (= Scolpolamin) statt<br />
<br />
Zwangsjacke. Zeitschrift fur Phytotherapie 5 (3):<br />
<br />
840-41.</td><br />
</tr><br />
<br />
</table></div>
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