Tropane alkaloid

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Chemical structure of tropane which forms the core of tropane alkaloids Tropane.svg
Chemical structure of tropane which forms the core of tropane alkaloids
Chemical structure and phylogeny of tropane alkaloids. Displayed are 3 chemical compounds that occur as natural products in 5 plant species Tropane alkaloids biochemistry.png
Chemical structure and phylogeny of tropane alkaloids. Displayed are 3 chemical compounds that occur as natural products in 5 plant species

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. [1] Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. [2] [3] [4] [5] [6] [7] Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.

Contents

Classification

Anticholinergics

Anticholinergic drugs [8] and deliriants: [9] [10] [11] [12] [13]

All three acetylcholine-inhibiting chemicals can also be found in the leaves, stems, and flowers in varying, unknown amounts in Brugmansia (angel trumpets), a relative of Datura . The same is also true of many other plants belonging to subfamily Solanoideae of the Solanaceae, the alkaloids being concentrated particularly in the leaves and seeds. However, the concentration of alkaloids can vary greatly, even from leaf to leaf and seed to seed. [14] [15]

Stimulants

Stimulants and cocaine-related alkaloids: [10] [16]

Others

Synthetic analogs of tropane alkaloids also exist, such as the phenyltropanes. They are not considered to be alkaloids per definition.

Biosynthesis

The biosynthesis of the tropane alkaloids have attracted intense interest because of their high physiological activity as well as the presence of the bicyclic tropane core. [17]

Final stages in the pathway for the biosynthesis of the tropane alkaloid cocaine. CocaineBiosyn2.png
Final stages in the pathway for the biosynthesis of the tropane alkaloid cocaine.

References

  1. ↑ O'Hagan D (2000). "Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids (1998 to 1999)". Natural Product Reports. 17 (5): 435–446. doi:10.1039/a707613d. PMID   11072891.
  2. ↑ Hesse M (2002). Alkaloids: Nature's Curse or Blessing?. Weinheim: Wiley-VCH. p. 304. ISBN   978-3-906390-24-6.
  3. ↑ Ryzik M (10 June 2007). "Cocaine: Hidden in Plain Sight". The New York Times. Archived from the original on 11 August 2017. Retrieved 18 May 2017.
  4. ↑ "The Buyers – A Social History of America's Most Popular Drugs". FRONTLINE. PBS. Archived from the original on 14 May 2017. Retrieved 18 May 2017.
  5. ↑ Anderson L. "Devil's Breath: Urban Legend or the World's Most Scary Drug?". Drugs.com. Retrieved 9 July 2019.
  6. ↑ Fatur K (June 2020). ""Hexing Herbs" in Ethnobotanical Perspective: A Historical Review of the Uses of Anticholinergic Solanaceae Plants in Europe" . Economic Botany. 74 (2): 140–158. Bibcode:2020EcBot..74..140F. doi:10.1007/s12231-020-09498-w. ISSN   0013-0001. S2CID   220844064.
  7. ↑ Rätsch C (2005). The Encyclopedia of Psychoactive Plants: Ethnopharmacology and Its Applications. Park Street Press. ISBN   978-0-89281-978-2.
  8. ↑ Grynkiewicz G, Gadzikowska M (2008). "Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs". Pharmacological Reports. 60 (4): 439–463. PMID   18799813.
  9. ↑ Volgin AD, Yakovlev OA, Demin KA, Alekseeva PA, Kyzar EJ, Collins C, et al. (16 October 2018). "Understanding Central Nervous System Effects of Deliriant Hallucinogenic Drugs through Experimental Animal Models". ACS Chemical Neuroscience. 10 (1): 143–154. doi:10.1021/acschemneuro.8b00433. PMID   30252437. S2CID   52824516.
  10. 1 2 3 4 Kohnen-Johannsen KL, Kayser O (February 2019). "Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production". Molecules. 24 (4). Basel, Switzerland: 796. doi: 10.3390/molecules24040796 . PMC   6412926 . PMID   30813289.
  11. ↑ Sweta VR, Lakshmi T (2015). "Pharmacological profile of tropane alkaloids". Journal of Chemical and Pharmaceutical Research. 7 (5): 117–119.
  12. 1 2 3 Gong H, He P, Lan X, Zeng L, Liao Z (2022). "Biotechnological Approaches on Engineering Medicinal Tropane Alkaloid Production in Plants". Frontiers in Plant Science. 13: 924413. doi: 10.3389/fpls.2022.924413 . PMC   9201383 . PMID   35720595.
  13. 1 2 3 Christen P, Bieri S, Berkov S (2013). "Methods of analysis: Tropane alkaloids from plant origin.". Natural products. pp. 1009–1048. doi:10.1007/978-3-642-22144-6_35. ISBN   978-3-642-22144-6.
  14. ↑ Hawkes JG, Lester RN, Skelding AD, eds. (1979). The Biology and Taxonomy of the Solanaceae. Linnean Society Symposium Series. Vol. 7. Academic Press for the Linnean Society of London. ISBN   978-0-12-333150-2.
  15. ↑ Eich E (2008). Solanaceae and Convolvulaceae: Secondary Metabolites – Biosynthesis, Chemotaxonomy, Biological and Economic Significance (A Handbook). Berlin Heidelberg: Springer-Verlag. ISBN   978-3-540-74541-9.
  16. ↑ Roque Bravo R, Faria AC, Brito-da-Costa AM, Carmo H, Mladěnka P, Dias da Silva D, et al. (April 2022). "Cocaine: An Updated Overview on Chemistry, Detection, Biokinetics, and Pharmacotoxicological Aspects including Abuse Pattern". Toxins. 14 (4): 278. doi: 10.3390/toxins14040278 . PMC   9032145 . PMID   35448887.
  17. ↑ Leete E (Aug 1990). "Recent Developments in the Biosynthesis of the Tropane Alkaloids1". Planta Medica. 56 (4): 339–352. Bibcode:1990PlMed..56..339L. doi: 10.1055/s-2006-960979 . PMID   2236285.
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