Hyoscyamine

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Structural formula
Structure of hyoscyamine
General
Surname Hyoscyamine
other names
  • ( S ) - (-) - hyoscyamine
  • L - (-) - hyoscyamine
  • ( S ) -3-Hydroxy-2-phenylpropionic acid (1 R , 3 R , 5 S ) -8-methyl-8-azabicyclo [3.2.1] oct-3-yl ester
Molecular formula C 17 H 23 NO 3
External identifiers / databases
CAS number 101-31-5
EC number 202-933-0
ECHA InfoCard 100.002.667
PubChem 154417
DrugBank DB00424
Wikidata Q413762
Drug information
ATC code

A03 BA03

Drug class

Anticholinergic , antispasmodic

properties
Molar mass 289.37 g · mol -1
Physical state

firmly

Melting point

108.5 ° C

pK s value

11.72

solubility

poor in water (3.56 g l −1 at 20 ° C)

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: 300 + 330
P: 301 + 310 + 330-304 + 340 + 310
Toxicological data

95 mg kg −1 ( LD 50 ,  mouse ,  iv )

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

Hyoscyamine is a natural substance and at the same time a biologically active tropane alkaloid .

Occurrence

The black deadly nightshade ( Atropa bella-donna ) contains ( S ) - (-) - hyoscyamine.

The biologically active ( S ) -hyoscyamine is often found in nightshade plants , for example in thorn apple , mandrake , angel's trumpet , deadly nightshade and henbane . The Heidelberg pharmacist Philipp Lorenz Geiger is considered to be the discoverer .

Effect and use

As an anticholinergic, this toxic substance antagonizes the effects of the body's own neurotransmitter acetylcholine by blocking acetylcholine receptors.

The racemic mixture ( R , S ) -hyoscyamine ( atropine ) is used therapeutically as a parasympatholytic , spasmolytic and mydriatic , but also as an antidote for poisoning with insecticides and pesticides . Before the introduction of modern psychotropic drugs , hyoscyamine was used in psychiatry to treat states of agitation.

Analytics

The reliable qualitative and quantitative determination of the hyoscyamine can be carried out after sufficient sample preparation by coupling the HPLC with the mass spectrometry .

Web links

Individual evidence

  1. ↑ a b c Entry on hyoscyamine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  2. ↑ a b c Entry on hyoscyamine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. ↑ Entry on Hyoscyamine 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 .
  4. ^ Geiger, Philipp Lorenz. In: Edward Kremers, George Urdang: Kremers and Urdang's History of Pharmacy. Reprint of the 4th Edition. American Institute of the History of Pharmacy, Madison WI 1986, ISBN 0-931292-17-4 , p. 459.
  5. ↑ Hans C. Bangen: History of the drug therapy of schizophrenia. VWB, Verlag für Wissenschaft und Bildung, Berlin 1992, ISBN 3-927408-82-4 , p. 23 (At the same time: Berlin, Free University, dissertation).
  6. ↑ T. Konishi, K. Akaki, K. Hatano: Determination of hyoscyamine and scopolamine in serum and urine of humans by liquid chromatography with tandem mass spectrometry. In: Shokuhin Eiseigaku Zasshi. 49 (4), Aug 2008, pp. 266-271. PMID 18787311 (Japanese)
  7. ^ H. John, J. Mikler, F. Worek, H. Thiermann: Application of an enantioselective LC-ESI MS / MS procedure to determine R- and S-hyoscyamine following intravenous atropine administration in swine. In: Drug Test Anal. 4 (3-4), Mar-Apr 2012, pp. 194-198. PMID 21964777