The result of the enzymatic reaction between indoleamines and a donor of one-carbon units, 5-methyl-tetrahydrofolic acid (5-MTHF), has been thought to be an N- or O-methylation of the indoleamine. We find that an enzymatic preparation from human platelets uses 5MTHF as a cofactor to convert tryptamine and two tryptamine derivatives to tryptolines (tetrahydro-β-carbolines), a class of tricyclic compounds. These products were identified by thin-layer chromatography, cocrystallization, and gas liquid chromatography/mass spectrometry. Formation of these compounds in mammalian tissues has not previously been described, to our knowledge. Platelet activity in healthy volunteers showed large individual variations; values for women were higher than those for men. These findings suggest the need for further examination of the pharmacological and psychological effects of tryptolines.
Barchas JD, Elliott GR, DoAmaral J, Erdelyi E, O'Connor S, Bowden M, Brodie HKH, Berger PA, Renson J, Wyatt RJ. TriptolinesFormation From Tryptamines and 5-MTHF by Human Platelets. Arch Gen Psychiatry. 1974;31(6):862-867. doi:10.1001/archpsyc.1974.01760180100013