Table 1.
Summary of binding data for N,N-diallyltryptamine (DALT) and ring-substituted derivatives at 33 receptors and transporters.
| Site | Speciesa | Binding Affinity (Ki, nM) | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| DALT | 5-MeO | 5-F | 5-Br | 4-HO | 4-AcO | 2-Ph | 5-MeO-2-Me | 5-F-2-Me | 7-Et | ||
| 5-HT1A | Human | 100 | 19 | 80 | 11 | 319 | 383 | 402 | 267 | 318 | 1,013 |
| 5-HT1B | Human | > 10,000 | 735 | 1,787 | 950 | 2,494 | > 10,000 | 273 | 2,267 | 2,011 | > 10,000 |
| 5-HT1D | Human | 689 | 107 | 816 | 130 | 693 | 801 | 204 | 900 | 1,592 | 2,691 |
| 5-HT1E | Human | 378 | 500 | 474 | 512 | 238 | 467 | > 10,000 | 1,594 | 1,273 | > 10,000 |
| 5-HT2A | Human | 701 | 218 | 247 | 477 | 652 | 565 | 13 | 1,153 | 655 | 1,515 |
| 5-HT2B | Human | 61 | 59 | 16 | 53 | 2,593 | 63 | 192 | 241 | 17 | 65 |
| 5-HT2C | Human | 385 | 456 | 102 | 358 | 2,113 | 1,515 | 278 | > 10,000 | 541 | 443 |
| 5-HT5A | Human | > 10,000 | 3,312 | 4,299 | 2,389 | > 10,000 | 5,844 | 1,670 | 1,822 | 1,916 | > 10,000 |
| 5-HT6 | Human | 1,718 | 153 | 74 | 133 | 213 | 1,791 | 68 | 206 | 168 | > 10,000 |
| 5-HT7 | Human | > 10,000 | 90 | 402 | 49 | 600 | 724 | > 10,000 | > 10,000 | 493 | > 10,000 |
| SERT | Human | 150 | 499 | 36 | 127 | 5,210 | 1,089 | > 10,000 | > 10,000 | 983 | 795 |
| α1A | Human | 1,663 | > 10,000 | 1,251 | 637 | > 10,000 | > 10,000 | 75 | 1,198 | 1,570 | > 10,000 |
| α1B | Human | 1,369 | > 10,000 | > 10,000 | 2,050 | > 10,000 | > 10,000 | 904 | > 10,000 | > 10,000 | > 10,000 |
| α1D | Human | > 10,000 | > 10,000 | > 10,000 | 1,124 | > 10,000 | > 10,000 | 243 | 2,405 | > 10,000 | > 10,000 |
| α2A | Human | 124 | 215 | 119 | 83 | 1,206 | 342 | 85 | 189 | 53 | 141 |
| α2B | Human | 305 | 726 | 218 | 227 | > 10,000 | 170 | 78 | 335 | 108 | 489 |
| α2C | Human | 901 | 1,467 | 848 | 356 | > 10,000 | 748 | 159 | 888 | 184 | 682 |
| NET | Human | 1,121 | > 10,000 | 1,818 | 964 | > 10,000 | > 10,000 | 420 | > 10,000 | > 10,000 | 1,879 |
| D1 | Human | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | 2,793 | > 10,000 | > 10,000 | > 10,000 |
| D2 | Human | > 10,000 | > 10,000 | 2,463 | 4,349 | > 10,000 | > 10,000 | 388 | > 10,000 | 4,416 | > 10,000 |
| D3 | Human | 672 | > 10,000 | 120 | 240 | 1,570 | > 10,000 | 342 | 2,399 | 414 | 1,082 |
| D4 | Human | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | 1,000 | > 10,000 | > 10,000 | > 10,000 |
| D5 | Human | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | 2,003 | > 10,000 | > 10,000 | > 10,000 |
| DAT | Human | 1,406 | 3,378 | 2,150 | 2,455 | > 10,000 | > 10,000 | 746 | 2,413 | 2,208 | 1,725 |
| MOR | Human | > 10,000 | > 10,000 | > 10,000 | 1,726 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | 2,674 |
| DOR | Human | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | 6,789 | > 10,000 | > 10,000 | > 10,000 |
| KOR | Human | 2,477 | 1,132 | 2,184 | 898 | > 10,000 | 5,235 | 589 | 391 | 580 | 580 |
| PBR | Rat kidneyb | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | 1,929 | > 10,000 | > 10,000 | > 10,000 |
| H1 | Human | 127 | 505 | 83 | 106 | > 10,000 | 353 | 79 | 847 | 435 | 913 |
| H2 | Human | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | > 10,000 | 367 | > 10,000 | > 10,000 | > 10,000 |
| H3 | Guinea pig | > 10,000 | 1,712 | 2,093 | 1,495 | > 10,000 | > 10,000 | > 10,000 | 1,134 | 1,397 | > 10,000 |
| σ1 | Rat brainb | 101 | 301 | 86 | 101 | 2,765 | 299 | > 10,000 | 427 | 531 | 22 |
| σ2 | Rat PC12b | 356 | 253 | 303 | 224 | > 10,000 | > 10,000 | 717 | 1,235 | 396 | 136 |
The experiments were performed using cloned receptors from the species indicated.
The experiment was performed using tissues or cells natively expressing the receptor.
Abbreviations: 2-Ph, 2-phenyl-N,N-diallyltryptamine; 4-AcO, 4-acetoxy-N,N-diallyltryptamine; 4-HO, 4-hydroxy-N,N-diallyltryptamine; 5-Br, 5-bromo-N,N-diallyltryptamine; 5-F, 5-fluoro-N,N-diallyltryptamine; 5-F-2-Me, 5-methoxy-2-fluoro-N,N-diallyltryptamine; 5-MeO, 5-methoxy-N,N-diallyltryptamine; 5-MeO-2-Me, 5-methoxy-2-methyl-N,N-diallyltryptamine; 7-Et, 7-ethyl-N,N-diallyltryptamine; DALT, N,N-diallyltryptamine; DAT, dopamine transporter; DOR, δ-opioid receptor; KOR, κ-opioid receptor; MOR, μ-opioid receptor; NET, norepinephrine transporter; PBR, peripheral benzodiazepine receptor; SERT, serotonin transporter.