EI and CI Mass Fragmentation of Tryptamine, Tetrahydro-beta-Carboline and Some of their Derivatives.

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Abstract
EI and CI mass spectra of tryptamine and eleven of its derivatives, as well as those of tetrahydro-.beta.-carboline (1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, THBC) and twelve of its derivatives were recorded and interpreted. An intense ion, most probably possessing a quinolinium ion structure, is produced from tryptamine derivatives by EI. The retro-Diels-Alder reaction is a prominent EI fragmentation pathway of .beta.-carbolines (BC''s), and a bulky 1-substituent os also easily split off. CI causes ammonia expulsion from tryptamine derivatives with a primary amino group in the side-chain; in the case of secondary amines and tryptophan derivatives, (MH)+ is the base peak when methane is used as the reaction gas. (MH)+ is the base peak in the CI spectra of BC derivatives, except in the case of derivatives which have a free carboxyl group, the loss of which often yields the base peak.

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