Scopoletin

From TripSit wiki
Jump to navigation Jump to search
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.