Fig 1.
General structure and numbering of the N-benzyltryptamines.
R5 = H, tryptamines; R5 = MeO, 5-methoxytryptamines.
Table 1.
Human 5-HT2 receptor subtype binding affinities (pKi ± SEM, and Ki in parentheses) and 5-HT2A/2C and (in parentheses) 5-HT2C/2A selectivities of serotonin, tryptamine, and the synthesized compounds.
Table 2.
Human 5-HT2 receptor subtype Ca2+ mobilization potencies (pEC50 ± SEM, and EC50 in parentheses) and relative efficacies (% of response to 5-HT), and 5-HT2A/2C and (in parentheses) 5-HT2C/2A selectivities of serotonin, tryptamine, and the synthesized compounds.
Fig 2.
Synthesis of N-(substituted)benzyltryptamines.
a: MeOH, r.t., overnight; b: NaBH4 in small portions, r.t.
Fig 3.
Intramolecular hydrogen bond in N-(2’-hydroxybenzyl)tryptamines.
Fig 4.
Possibly psychedelic N-benzyl-5-methoxytryptamines.
Fig 5.
5-HT2C-selective N-benzyltryptamines.
Fig 6.
Structure and 5-HT2A and 5-HT2C functional potencies of lorcaserin.