2-Methyltryptoline
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| 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) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.440.994 |
PubChem CID |
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CompTox Dashboard (EPA) |
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| 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).
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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] Anadenanthera peregrina,[11] Anadenanthera colubrina,[11] in cereal plants such as Arundo donax,[12] Phalaris arundinacea,[13] Phalaris aquatica,[14] Phalaris coerulescens,[15] in Papaveraceae as Papaver rhoeas,[14] in Solanaceae such as Solanum jabrense,[16] in some Elaeagnaceae, such as Elaeagnus angustifolia[17] and has been imprinted in Cyathobasis fruticulosa.[18][19]