Table 1 Binding affinity of phenethylamine derivatives for 5-HT2AR.
| Compd | R1 | R2 | R3 | R4 | R5=R6=R7 | Ki (nM) | |
|---|---|---|---|---|---|---|---|
| 1 | -CH2CH2CH3 | -H | -H | -H | -H | 3.473 | |
| 2 | -NO2 | -H | -H | -H | -H | 25.17 | |
| 3 | -OCH2C(CH3)=CH2 | -H | -H | -H | -H | 71.92 | |
| 4 | -Cl | -H | -H | -H | -H | 13.04 | |
| 5 | -CH3 | -OCH3 | -H | -H | -H | 1.907 | |
| 6 | -CH3 | -H | -Ar | -OCH3 | -H | 2.881 | |
| 7 | -CH2CH3 | -H | -Ar | -OCH3 | -H | 1.524 | |
| 8 | -Cl | -H | -Ar | -OCH3 | -H | 0.817 | |
| 9 | -Br | -H | -Ar | -OCH3 | -H | 1.411 | |
| 10 | -Cl | -H | -Ar | -OH | -H | 1.099 | |
| 11 | -Cl | -H | -Ar | -F | -H | 10.84 | |
| 12 | -Br | -H | -Ar | -F | -H | 3.629 | |
| 13 | -I | -H | -Ar | -F | -H | 10.00 | |
| 14 | -Cl | -H | -Ar | -H | -OCH3 | 515.1 | |
| Ketanserin | 22.21 | ||||||
1. 2C-P HCl: 2,5-dimethoxy-4-propyl-benzeneethanamine, HCl.
2. 2C-N HCl: 2,5-Dimethoxy-4-nitrophenethylamine, HCl.
3. Methallylescaline HCl.
4. 2C-C HCl: 4-Chloro-2,5-Dimethoxyphenethylamine, HCl.
5. BOD HCl: 4-methyl-2,5,beta-trimethoxyphenethylamine, HCl.
6. 25D-NBOMe HCl: 2-(2,5-dimethoxy-4-methylphenyl)-N-(2-methoxybenzyl)ethanamine, HCl.
7. 25E-NBOMe HCl: 2-(4-ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine, HCl.
8. 25C-NBOMe HCl: 2-(4-chloro-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine, HCl.
9. 25B-NBOMe HCl: 4-bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]-benzeneethanamine, HCl.
10. 25C-NBOH HCl: 2-[[[2-(4-chloro-2,5-dimethoxyphenyl)ethyl]amino]methyl]-phenol, HCl.
11. 25C-NBF HCl: 4-chloro-N-[(2-fluorophenyl)methyl]-2,5-dimethoxy-benzeneethanamine, HCl.
12. 25B-NBF HCl: 4-bromo-N-[(2-fluorophenyl)methyl]-2,5-dimethoxy-benzeneethanamine, HCl.
13. 25I-NBF HCl: N-(2-fluorobenzyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethanamine, HCl.
14. 30C-NBOMe HCl: 2-(4-chloro-2,5-dimethoxyphenyl)-N-(3,4,5-trimethoxybenzyl)ethanamine, HCl.