Mesembrine

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Structural formula
Mesembrine structural formula
Structural formula of (-) - mesembrine
General
Surname Mesembrine
other names

3a- (3,4-Dimethoxyphenyl) -1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one

Molecular formula C 17 H 23 NO 3
Brief description

oily liquid [(-) - mesembrine]

External identifiers / databases
CAS number
  • 24880-43-1 [(-) - mesembrine]
  • 468-53-1 [(+) - mesembrine]
PubChem 394162
ChemSpider 349381
Wikidata Q56450441
properties
Molar mass 289.37 g mol −1
Physical state

liquid

boiling point

186–190 ° C (40 Pa) [(-) - mesembrine]

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mesembrine is a chemical compound that belongs to the group of indole alkaloids . There are two isomeric forms, (+) - mesembrine and the naturally occurring (-) - mesembrine.

Isomers

Isomers of mesembrine
Surname (+) - mesembrine (-) - Mesembrine
other names (3a R , 7a R ) -3a- (3,4-dimethoxyphenyl) -1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one (3a S , 7a S ) -3a- (3,4-dimethoxyphenyl) -1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one
CAS number 468-53-1 24880-43-1
PubChem 193296 394162
499683 (undefined)
Wikidata Q2580349 Q56450441

Occurrence

Mesembryanthemum crystallinum

(-) - Mesembrine occurs in the plant genus Mesembryanthemum , as well as in Sceletium . However, there is disagreement about the exact categorization of the Sceletium genus. These plants have no thorns or thorns. The poisonous compound is therefore probably used to protect against being eaten.

Crystal structure

To determine the structure of the mesembrin, the crystal structure of the derivative 6-epimesembranol methiodide was determined in 1970. The crystal structure of this compound is monoclinic with space group P 2 1 (No. 4) . Template: room group / 4

effect

The effect is both sedative and stimulating in nature. It is partly compared to the effects of cocaine . It can be explained , among other things, by the inhibition of the uptake of serotonin . In connection with amphetamines can for serotonin syndrome come. The effects can be increased by alcohol. Mesembrine also inhibits the enzyme PDE4 .

The natives of South Africa use dried parts of plants as intoxicants ( Kanna ). The effect is mainly antidepressant, which is due to the blocking of the serotonin transporter .

Individual evidence

  1. ↑ a b Entry on mesembrine alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on September 2, 2016.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ a b P. Coggon, DS Farrier, PW Jeffs, AT McPhail: Absolute configuration of mesembrine and related alkaloids: X-ray analysis of 6-epimesembranol methiodide . In: J. Chem. Soc. B . 1970, p. 1267-1271 , doi : 10.1039 / j29700001267 .
  4. ^ JS Glasby: Directory Of Plants Containing Secondary Metabolites . Taylor & Francis, London, New York 1991, ISBN 978-0-85066-423-2 , pp. 780 .
  5. ^ MT Smith, NR Crouch, N. Gericke, M. Hirst: Psychoactive constituents of the genus Sceletium NEBr. and other Mesembryanthemaceae: a review . Ed .: Journal of Ethnopharmacology. tape 50 , no. 3 , 1996, p. 119-130 .
  6. ↑ a b Chemistry - Kanna Info. In: Kanna-Info. Retrieved February 2, 2018 .
  7. ^ Y. Delange: Succulents . Eugen Ulmer, Stuttgart 2007, ISBN 978-3-8001-4992-6 , pp. 70 .
  8. ↑ Mesembrine. In: Drugs Wiki. Retrieved February 2, 2018 .
  9. ↑ AL Harvey, LC Young, AM Viljoen, NP Gericke: Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloids. In: Journal of ethnopharmacology. Volume 137, number 3, October 2011, pp. 1124-1129, doi : 10.1016 / j.jep.2011.07.035 , PMID 21798331 .