Scopolamine

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of L-scopolamine
General
Surname Scopolamine
other names
  • L - (-) - scopolamine
  • L - (-) - hyoscine
  • L -6,7-epoxytropyl tropate
  • 3-Hydroxy-2-phenylpropionic acid 9-methyl-3-oxa-9-azatricyclo [3.3.1.0 2,4 ] non-7-yl ester
  • (9-methyl-3-oxa-9-azatricyclo [3.3.1.0 2,4 ] non-7-yl) -3-hydroxy-2-phenylpropanoate
Molecular formula C 17 H 21 NO 4
Brief description

colorless, viscous oil or colorless crystals (as monohydrate)

External identifiers / databases
CAS number
  • 51-34-3 [ L - (-) - scopolamine]
  • 138-12-5 [(±) -Scopolamine]
  • 55-16-3 [hydrochloride]
  • 6533-68-2 [hydrobromide trihydrate]
EC number 200-090-3
ECHA InfoCard 100,000,083
PubChem 153311
DrugBank DB00747
Wikidata Q337188
Drug information
ATC code
Drug class
properties
Molar mass 303.36 g · mol -1
Physical state

firmly

Melting point

59 ° C (as monohydrate)

pK s value

7.75

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic

danger

H and P phrases H: 330-310-300
P: 260-264-280-284-301 + 310-302 + 350
Toxicological data

1275 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Scopolamine , also known as hyoscine , is a chemical compound that belongs to the tropane alkaloids .

Occurrence and extraction

Common thorn apple ( Datura stramonium )

Scopolamine is found in nightshade plants such as thorn apple , henbane , mandrake and especially in angel's trumpets ( Brugmansia ), but can also be produced artificially. Chemically, it is an ester of scopine and tropic acid and is closely related to atropine .

effect

At low doses, scopolamine has a slightly calming and inhibiting effect on the vomiting center in the brain. At higher doses it has a dampening effect and creates a state of apathy . Since it can also cause a state of willlessness in this case, it was used as a truth serum in the 1950s until the advent of sodium pentothal , which goes back to the Texan doctor Robert Ernest House (1924), who also used it in the Verification of suspects touted.

Until the introduction of neuroleptics , scopolamine was successfully used together with morphine-based preparations to calm down highly excited mentally ill people. During parabolic flights , scopolamine (formerly together with the prescription drug dexamphetamine , now with caffeine ) is administered to calm the digestive tract.

The effect of scopolamine is due to its antagonistic effect on muscarinic acetylcholine receptors . Just like atropine, it acts as a competitive inhibitor.

Scopolamine, especially as an anticholinergic , has the following side effects (dose below 5 milligrams, non-subcutaneous):

Therapeutic use

N -Alkylation of scopolamine leads to quaternary derivatives (for example N -butylscopolamine , N -methylscopolamine) which, because of their constant positive charge on quaternary nitrogen, are so polar that they can not cross the blood-brain barrier , regardless of their environment . In contrast to scopolamine, butylscopolamine is therefore not centrally effective. It is used as a remedy for smooth muscle cramps, so-called colic .

Absorption and distribution in the body

Oral bioavailability is about 30% as opposed to about 50% for atropine. The half-life of scopolamine is shorter than that of atropine, but the blood-brain barrier can be overcome much better. Only about 6% are renally eliminated unchanged .

Use and abuse as a narcotic drug

Warnings should be given against misuse as a narcotic drug. The content in individual plants, the effects of which have been known for centuries, can vary widely. Due to the relatively narrow therapeutic range , serious side effects can occur. Scopolamine poisoning manifests itself as a parasympathetic blockade such as pupillary dilation or accommodation disorders and dryness of the mucous membranes. Eventually, there is deep unconsciousness and death from respiratory paralysis. The therapy is the same as for atropine poisoning: non-drug temperature reduction, artificial respiration for impending respiratory paralysis and administration of the antidote physostigmine salicylate .

According to reports, scopolamine - also called “Burundanga” there - was used by criminals as a knockout drop in Latin American countries to render victims willless. The odorless and tasteless agent is administered with food and beverages or it is inhaled through prepared cigarettes.

Some reports of drug use being circulated are false. At the turn of the year 2008/2009, several US police stations made it clear that the original report did not come from them and that employees themselves had fallen for the false report .

In Germany, too, a false report about the abuse of scopolamine has been circulating on the social networks Facebook and WhatsApp since 2013 , according to which criminals allegedly drugged their victims with the substance and then robbed or raped them. The drug is said to have been applied subcutaneously using small needles sewn into women's gloves and used in numerous major German cities. In December 2013, however, the Stuttgart Police Headquarters clarified on its Facebook page that this was a false report.

Individual evidence

  1. ↑ a b c Entry on scopolamine. In: Römpp Online . Georg Thieme Verlag, accessed on June 21, 2014.
  2. ↑ a b Entry on scopolamine in the GESTIS substance database of the IFA , accessed on February 21, 2017(JavaScript required) .
  3. ↑ a b Entry on scopolamine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ Entry on Hyoscine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ Data sheet (-) - Scopolamine hydrobromide trihydrate from Sigma-Aldrich , accessed on May 28, 2017 ( PDF ).
  6. ↑ Heinz Lüllmann , Klaus Mohr, Lutz Hein : Pharmacology and Toxicology. Understand drugs - use drugs in a targeted manner A textbook for students of medicine, pharmacy and life sciences, a source of information for doctors, pharmacists and health policymakers. 16th, completely revised edition. Thieme, Stuttgart et al. 2006, ISBN 3-13-368516-3 .
  7. ↑ Hans Bangen: History of the drug therapy of schizophrenia. Berlin 1992, ISBN 3-927408-82-4 , pp. 13-21.
  8. ^ Eberhard Aulbert, Friedemann Nauck, Lukas Radbruch (eds.): Textbook of Palliative Medicine . 2nd, completely revised and expanded edition. Schattauer, Stuttgart et al. 2007, ISBN 978-3-7945-2361-0 .
  9. ↑ Claus-Jürgen Estler, Harald Schmidt (Ed.): Pharmacology and Toxicology . 6., completely revised and exp. Edition. Schattauer, Stuttgart 2007, ISBN 978-3-7945-2295-8 , pp. 109 .
  10. ^ Hans Marquardt, Siegfried Schäfer, Holger Barth (eds.): Toxikologie . 3rd, completely revised and exp. Edition. Wissenschaftliche Verlagsgesellschaft, Stuttgart 2013, ISBN 3-8047-2876-6 , p. 1011 .
  11. ^ Jürgen Müller : Pharmaca diabolica and Pocula amatoria. On the cultural history of the Solanaceae alkaloids atropine and scopolamine. In: Würzburger medical historical research 17, 1998, pp. 361–373.
  12. ↑ Steve Hide: Latin America: Victims of drugging and mugging . telegraph.co.uk, February 5, 2001.
  13. ↑ Burundanga - False. snopes.com, Urban Legends Reference Page, version dated March 2, 2009.
  14. ^ Burundanga Business Card Drug Warning. - Status: Unsubstantiated Urban Legend, hoax-slayer.com, Accessed: March 24, 2009.
  15. ↑ David Emery: Burundanga Drug Warning. (Circulating since: May 2008, Status: Mostly false), urbanlegends.about.com, as of September 18, 2008.
  16. ↑ mimikama.at, The needle in the women's glove - as of November 28, 2014.