Table 2.
DA, 5HT, and NE Uptake Inhibition Properties and 5-HT2A, 5-HT2A β-arrestin, and 5-HT1A Activity of Psychedelic Tryptamines
 | |||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| # | Name | X | R1 | R2 | IC50, (nM)a | 5-HT2Ab | 5-HT1Ab | 5-HT2A β-arrestinc | Psychoactive Effectsd |
||||||
| DAT | SERT | NET | EC50, (nM) |
Emax, (%) |
EC50, (nM) |
Emax, (%) |
EC50, (nM) |
Emax, (%) |
|||||||
| 19 | DET | H | Et | Et | >10,000 | 258 ± 13 | >10,000 | 67.8 ± 4.4 | 90 ± 6 | IA | IA | Psychoactive, visuals, vertigo | |||
| 20 | NIPT | H | iPr | H | >10,000 | 1487 ± 93 | >10,000 | 116 ± 8.4 | 96 ± 3 | IA | >10,000 | Light-headed intoxicant, pleasant buzz | |||
| 21 | DPT | H | Pr | Pr | 2218 ± 168 | 157 ± 16 | 3202 ± 330 | 26.1 ± 1.9 | 97 ± 3 | IA | 1692 ± 78.9 | 63 ± 8 | Intensely visual, long lasting, things appear fast, religious experiences | ||
| 22 | DIPT | H | iPr | iPr | 4788 ± 416 | 288 ± 2.3 | >10,000 | 33.5 ± 1.5 | 110 ± 2 | IA | >10,000 | Auditory, not visual, heard voices, sounds had “golden spikes”, religious overtones | |||
| 23 | MIPT | H | iPr | Me | >10,000 | >10,000 | >10,000 | 44.9 ± 1.7 | 74 ± 5 | IA | IA | Mild hallucinations, stimulant, fast onset, psychedelic | |||
| 24 | Psilocin | 4-OH | Me | Me | >10,000 | 662 ± 41 | >10,000 | 45.2 ± 4.1e | 76 ± 7e | ND | ND | Very visual, lots of colors, better at night | |||
| 25 | 5MeO-T | OMe | H | H | >10,000 | 4000 | >10,000 | 0.503 ± 0.09 | 119 ± 2 | 183 ± 30 | 66 ± 4 | 535 ± 123 | 135 ± 20 | Not particularly active, possibly due to metabolism similar to 12 | |
| 7 | 5MeO-DMT | OMe | Me | Me | >10,000 | 2184 ± 222 | >10,000 | 3.87 ± 0.35 | 101 ± 4 | 791 ± 133 | 68 ± 3 | 385 ± 112 | 56 ± 6 | Time distortions, stoned feeling, hallucinogenic at high doses | |
| 26 | 5MeO-DET | OMe | Et | Et | >10,000 | 2410 ± 222 | >10,000 | 8.11 ± 0.36 | 101 ± 0.8 | 911 ± 186 | 67 ± 2 | 1065 ± 607 | 64 ± 8 | Auditory changes, negative experiences, anxiety | |
| 27 | 5MeO-NIPT | OMe | iPr | H | >10,000 | 5442 ± 377 | >10,000 | 9.24 ± 1.3 | 101 ± 2 | >10,000 | 1075 ± 234 | 99 ± 6 | NR | ||
| 28 | 5MeO-DPT | OMe | Pr | Pr | 16998 ± 2192 | 1031 ± 140 | >10,00 | 6.00 ± 0.43 | 101 ± 3 | 476 ± 102 | 43 ± 5 | 993 ± 421 | 68 ± 2 | Comfortable at low doses, oscillating good and bad sounds, negative side dominated as buzz continues | |
| 1 | 5MeO-DIPT | OMe | iPr | iPr | >10,000 | 646 ± 48 | >10,000 | 6.22 ± 1.1 | 109 ± 5 | >10,000 | 946 ± 141 | 124 ± 12 | Erotic, senses distorted, short-lived, could not make intuitive leaps | ||
| 2 | 5MeO-MIPT | OMe | iPr | Me | >10,000 | >10,000 | >10,000 | 7.82 ± 1.5 | 101 ± 3 | >10,000 | 566 ± 110 | 82 ± 13 | Fast onset, stimulates conceptual thought, depersonalization | ||
IA = Inactive at 10 µM in agonist screen.
NR = Not reported in TiHKAL.
ND = Not determined.
a
Uptake inhibition IC50 values are reported as means ± SD and are the result of N= 3 performed in triplicate.
b
Calcium mobilization EC50 and Emax values are reported as means ± SEM and are the result of three independent experiments performed in duplicate.
c
β-arrestin recruitment EC50 and Emax values are reported as means ± SEM and are the result of three independent experiments performed in duplicate.
d
Tabulated from anecdotal reports in TiHKAL.
e
Values are means ± SD and are the result of two independent experiments performed in duplicate.