2-Methyltryptoline

2-Methyltryptoline
Names
IUPAC name
2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
Other names
2-Methyl-1,2,3,4-tetrahydro-β-carboline; 2-Me-THβC
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.440.994 Edit this at Wikidata
  • InChI=1S/C12H14N2/c1-14-7-6-10-9-4-2-3-5-11(9)13-12(10)8-14/h2-5,13H,6-8H2,1H3 checkY
    Key: JOFKCNJIUXPJAC-UHFFFAOYSA-N checkY
  • CN1CCC2=C(C1)NC3=CC=CC=C23
Properties
C12H14N2
Molar mass 186.258 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. ^ a b Rivier, Laurent; Lindgren, Jan-Erik (1972-04-01). ""Ayahuasca," the South American hallucinogenic drink: An ethnobotanical and chemical investigation". Economic Botany. 26 (2): 101–129. Bibcode:1972EcBot..26..101R. doi:10.1007/BF02860772. ISSN 1874-9364.
  2. ^ a b Estrella-Parra, Edgar Antonio; Almanza-Pérez, Julio Cesar; Alarcón-Aguilar, Francisco Javier (2019-08-01). "Ayahuasca: Uses, Phytochemical and Biological Activities". Natural Products and Bioprospecting. 9 (4): 251–265. doi:10.1007/s13659-019-0210-5. ISSN 2192-2209. PMC 6646606. 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. Bibcode:1984JEthn..10..195M. doi:10.1016/0378-8741(84)90003-5. ISSN 0378-8741. PMID 6587171.
  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. ^ a b 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. Bibcode:2007BBRC..356..118H. doi:10.1016/j.bbrc.2007.02.089. ISSN 0006-291X. PMID 17346675.
  6. ^ a b 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 248608. doi:10.1155/2013/248608. ISSN 2314-6141. PMC 3745933. 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. Bibcode:1985NeuL...55..179C. doi:10.1016/0304-3940(85)90016-3. ISSN 0304-3940. PMID 2582318.
  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.
  11. ^ Khuzhaev, V. U. (2004-03-01). "Alkaloids of the Flora of Uzbekistan, Arundo donax". Chemistry of Natural Compounds. 40 (2): 160–162. Bibcode:2004CNatC..40..160K. doi:10.1023/B:CONC.0000033935.05529.e8. ISSN 1573-8388.
  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. Bibcode:1976PChem..15..737G. doi:10.1016/S0031-9422(00)94432-7. ISSN 0031-9422.
  13. ^ a b PubChem. "2-Methyl-1,2,3,4-tetrahydro-beta-carboline". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-04-07.
  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. Bibcode:1998PChem..48..437A. doi:10.1016/S0031-9422(97)00946-1. ISSN 0031-9422.
  15. ^ Eich, Eckart, ed. (2008), "Tryptophan-derived Alkaloids", 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{{citation}}: CS1 maint: work parameter with ISBN (link)
  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". 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. Bibcode:2005JNAtP..68..956K. doi:10.1021/np0580006. ISSN 0163-3864. PMID 15974629.
  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. Bibcode:2005JNAtP..68..956K. doi:10.1021/np0580006. ISSN 0163-3864. PMID 15974629.

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