Mitragynine

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Structural formula
Structural formula of mitragynine
General
Surname Mitragynine
other names

(all- S , E ) -16.17-didehydro-9,17-dimethoxy-17,18-seco-20 α -yohimban-16 carbonsäuremethylester

Molecular formula C 23 H 30 N 2 O 4
External identifiers / databases
CAS number 4098-40-2
PubChem 3034396
ChemSpider 2298865
Wikidata Q414299
Drug information
Drug class

Opioid - analgesic

properties
Molar mass 398.50 g mol −1
Physical state

firmly

Melting point

102-106 ° C

boiling point

230-240 ° C

solubility

soluble in ethanol , chloroform and acetic acid

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 .

Mitragynine is a natural substance found in the kratom plant and belongs to the group of indole alkaloids .

Occurrence

Kratom plant ( Mitragyna speciosa )

The natural substance is obtained from the kratom plant ( Mitragyna speciosa ). The kratom plant contains about 0.25% mitragynine, the remaining alkaloids are indole alkaloids such as. B. Paynanthein , 7-hydroxymitragynine or ajmalicin .

Pharmacology and effects

Mitragynine is an analgesic , its effects are very similar to those of codeine , but without many of its side effects.

Use as an intoxicant

As early as the 19th century, kratom was used in traditional medicine in Malaysia as an opium substitute . The reason for this lies in the ability of mitragynine to bind to μ - and k - receptors , whereby an opium-like psychotropic effect occurs , at least at high doses . Mitragynine also has a stimulating effect on the motor centers of the central nervous system, especially in lower doses. However, there is a high health risk if it is consumed together with MAOIs . Several deaths have been described in combination with more potent µ-opioid receptor agonists. Long-term use can lead to dependence that is very similar to opioid addiction. Another side effect reported is hyperpigmentation of the cheeks.

further reading

  • EJ Shellard: The alkaloids of Mitragyna with special reference to those of Mitragyna speciosa, Korth. UNODC, Bulletin on Narcotics, 1974. pp. 41-55. Online version

Individual evidence

  1. ↑ a b c Lycaeum Entheogen Database: Mitragynine ( Memento from April 24, 2016 in the Internet Archive ), accessed July 10, 2020
  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. ↑ Francisco León et al.: Phytochemical characterization of the leaves of Mitragyna speciosa grown in USA In: Natural Product Communications 4, no. 7 (July 2009): 907-910.
  4. ↑ JB Harbourne: Phytochemical Dictionary. Taylor & Francis. 1998. p. 208. ISBN 0-7484-0620-4 .
  5. ↑ Kazuo Watanabe et al .: Pharmacological properties of some structurally related indole alkaloids contained in the Asian herbal medicines, hirsutine and mitragynine, with special reference to their Ca 2+ antagonistic and opioid-like effects. In: Raymond Bonnett, Wantanabee, H Watanabe: Pharmacological Research on Traditional Herbal Medicines. Taylor & Francis 1999. ISBN 90-5702-054-8 , p. 163 ff.
  6. ↑ Th. Velocity: Intoxicating drugs. Market forms and modes of action. Heidelberg, Dordrecht, London, New York: Springer, 2013. pp. 203 f. ISBN 978-3-642-30162-9 .
  7. ↑ R. Kronstrand, M. Roman, G. Thelander, A. Eriksson: Unintentional fatal intoxications with Mitragynine and O-desmethyltramadol from the herbal blend Krypton. In: Journal of analytical toxicology. Volume 35, Number 4, May 2011, pp. 242-247, PMID 21513619 .