Chemistry:2-Methyltryptoline

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2-Methyltryptoline, also known as 2-methyl-1,2,3,4-tetrahydro-β-carboline (2-Me-THβC), is a natural product, closely related to tryptoline. An indole alkaloid of the substituted β-carboline family, 2-methyltryptoline is found in the drink ayahuasca, where it was isolated from Psychotria viridis and Psychotria carthagenensis.[1][2][3] 2-Methyltryptoline is also found in some cereal and Papaveraceae plants.

Pharmacology

Pharmacodynamics

Little is known about the psychoactivity of 2-methyltryptoline; however, it is known to be a potent protoxin and, accordingly, a neurotoxin that acts similarly to MPTP (although it does not cause idiopathic Parkinson's disease) and it is assumed that it is an endogenous substance, in the long term it is a monoaminergic neurotoxin.[4][5][6][7][8][9]

2-Methyltryptoline is a reversible inhibitor of monoamine oxidase.[10]

Metabolism

2-Methyltryptoline to neurotoxic β-carbolinium cations[clarification needed] is carried out by heme-containing peroxidases (MPO, LPO), MAO (MAO-A or MAO-B, but they did not form active metabolites) and CYP2D6 which formed polar metabolites (hydroxylation at positions 6 and 7), which, judging by their nature, can be considered as detoxification metabolites.[5][6]

Natural occurrence

2-Methyltryptoline has been found in Psychotria viridis, Psychotria carthagenensis,[1][2] in cereal plants such as Arundo donax,[11] Phalaris arundinacea,[12] Phalaris aquatica,[13] Phalaris coerulescens,[14] in Papaveraceae as Papaver rhoeas,[13] in Solanaceae such as Solanum jabrense[15], in some Elaeagnaceae, such as Elaeagnus angustifolia[16] and has been imprinted in Cyathobasis fruticulosa.[17][18]

References

  1. ↑ 1.0 1.1 Rivier, Laurent; Lindgren, Jan-Erik (1972-04-01). ""Ayahuasca," the South American hallucinogenic drink: An ethnobotanical and chemical investigation" (in en). Economic Botany 26 (2): 101–129. doi:10.1007/BF02860772. ISSN 1874-9364. Bibcode: 1972EcBot..26..101R. 
  2. ↑ 2.0 2.1 Estrella-Parra, Edgar Antonio; Almanza-Pérez, Julio Cesar; Alarcón-Aguilar, Francisco Javier (2019-08-01). "Ayahuasca: Uses, Phytochemical and Biological Activities" (in en). Natural Products and Bioprospecting 9 (4): 251–265. doi:10.1007/s13659-019-0210-5. ISSN 2192-2209. PMID 31134518. 
  3. ↑ McKenna, D. J.; Towers, G. H.; Abbott, F. (1984). "Monoamine oxidase inhibitors in South American hallucinogenic plants: tryptamine and β-carboline constituents of Ayahuasca". Journal of Ethnopharmacology 10 (2): 195–223. doi:10.1016/0378-8741(84)90003-5. ISSN 0378-8741. PMID 6587171. Bibcode: 1984JEthn..10..195M. 
  4. ↑ Perry, T. L.; Yong, V. W.; Wall, R. A.; Jones, K. (1986-09-12). "Paraquat and two endogenous analogues of the neurotoxic substance N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine do not damage dopaminergic nigrostriatal neurons in the mouse". Neuroscience Letters 69 (3): 285–289. doi:10.1016/0304-3940(86)90495-7. ISSN 0304-3940. PMID 3489912. 
  5. ↑ 5.0 5.1 Herraiz, Tomás; Guillén, Hugo; Galisteo, Juan (2007-04-27). "N-methyltetrahydro-β-carboline analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxin are oxidized to neurotoxic β-carbolinium cations by heme peroxidases". Biochemical and Biophysical Research Communications 356 (1): 118–123. doi:10.1016/j.bbrc.2007.02.089. ISSN 0006-291X. PMID 17346675. Bibcode: 2007BBRC..356..118H. 
  6. ↑ 6.0 6.1 Herraiz, Tomás; Guillén, Hugo; Galisteo, Juan (2013). "Metabolite profile resulting from the activation/inactivation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and 2-methyltetrahydro-β-carboline by oxidative enzymes". BioMed Research International 2013. doi:10.1155/2013/248608. ISSN 2314-6141. PMID 23984327. 
  7. ↑ Perry, T. L.; Jones, K.; Hansen, S.; Wall, R. A. (1987-03-20). "4-phenylpyridine and three other analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine lack dopaminergic nigrostriatal neurotoxicity in mice and marmosets". Neuroscience Letters 75 (1): 65–70. doi:10.1016/0304-3940(87)90076-0. ISSN 0304-3940. PMID 3106859. 
  8. ↑ Collins, M. A.; Neafsey, E. J. (1985-04-09). "β-carboline analogues of N-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP): endogenous factors underlying idiopathic parkinsonism?". Neuroscience Letters 55 (2): 179–184. doi:10.1016/0304-3940(85)90016-3. ISSN 0304-3940. PMID 2582318. Bibcode: 1985NeuL...55..179C. 
  9. ↑ Barker, S. A.; Harrison, R. E.; Monti, J. A.; Brown, G. B.; Christian, S. T. (1981-01-01). "Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline, and 6-methoxy-1,2,3,4-tetrahydro-β-carboline as in vivo constituents of rat brain and adrenal gland". Biochemical Pharmacology 30 (1): 9–17. doi:10.1016/0006-2952(81)90278-1. ISSN 0006-2952. PMID 7213417. 
  10. ↑ Ho, Beng T.; McIsaac, William M.; Walker, Kenneth E.; Estevez, Vicente (1968-02-01). "Inhibitors of Monoamine Oxidase: Influence of Methyl Substitution on the Inhibitory Activity of β-Carbolines". Journal of Pharmaceutical Sciences 57 (2): 269–274. doi:10.1002/jps.2600570205. ISSN 0022-3549. PMID 5641670. https://www.sciencedirect.com/science/article/pii/S002235491536189X. 
  11. ↑ Khuzhaev, V. U. (2004-03-01). "Alkaloids of the Flora of Uzbekistan, Arundo donax" (in en). Chemistry of Natural Compounds 40 (2): 160–162. doi:10.1023/B:CONC.0000033935.05529.e8. ISSN 1573-8388. Bibcode: 2004CNatC..40..160K. 
  12. ↑ Gander, J. E.; Marum, P.; Marten, G. C.; Hovin, A. W. (1976-01-01). "The occurrence of 2-methyl-1,2,3,4-tetrahydro-β-carboline and variation in alkaloids in Phalaris arundinacea". Phytochemistry 15 (5): 737–738. doi:10.1016/S0031-9422(00)94432-7. ISSN 0031-9422. Bibcode: 1976PChem..15..737G. 
  13. ↑ 13.0 13.1 PubChem. "2-Methyl-1,2,3,4-tetrahydro-beta-carboline" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/121896. 
  14. ↑ Anderton, Neil; Cockrum, Peter A.; Colegate, Steven M.; Edgar, John A.; Flower, Kirsty; Vit, Ivan; Willing, Richard I. (1998-06-01). "Oxindoles from Phalaris coerulescens". Phytochemistry 48 (3): 437–439. doi:10.1016/S0031-9422(97)00946-1. ISSN 0031-9422. Bibcode: 1998PChem..48..437A. 
  15. ↑ Eich, Eckart, ed. (2008), "Tryptophan-derived Alkaloids" (in en), Solanaceae and Convolvulaceae: Secondary Metabolites: Biosynthesis, Chemotaxonomy, Biological and Economic Significance (A Handbook) (Berlin, Heidelberg: Springer): pp. 213–259, doi:10.1007/978-3-540-74541-9_4, ISBN 978-3-540-74541-9 
  16. ↑ Abizov, E. A.; Tolkachev, O. N. (2012-01-01). "Dynamics of accumulation and distribution of β-carboline alkaloids in Elaeagnus species cultivated in Moscow Region" (in en). Pharmaceutical Chemistry Journal 45 (10): 632–635. doi:10.1007/s11094-012-0691-6. ISSN 1573-9031. 
  17. ↑ Küçükosmanoǧlu Bahçeevli, Arzu; Kurucu, Semra; Kolak, Ufuk; Topçu, Gülaçtı; Adou, Eba; Kingston, David G. I. (2005-06-01). "Alkaloids and Aromatics of Cyathobasis fruticulosa (Bunge) Aellen". Journal of Natural Products 68 (6): 956–958. doi:10.1021/np0580006. ISSN 0163-3864. PMID 15974629. Bibcode: 2005JNAtP..68..956K. 
  18. ↑ Bahçeevli, Arzu Küçükosmanogiu; Kurucu, Semra; Kolak, Ufuk; Topçu, Gülaçti; Adou, Eba; Kingston, David G. I. (2005). "Alkaloids and aromatics of Cyathobasis fruticulosa (Bunge) Aellen". Journal of Natural Products 68 (6): 956–958. doi:10.1021/np0580006. ISSN 0163-3864. PMID 15974629. Bibcode: 2005JNAtP..68..956K. 

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