Biomolecules & Therapeutics : eISSN 2005-4483 / pISSN 1976-9148

Table. 2.

Table 2 Binding affinity of tryptamine derivatives for 5-HT2AR.

Compd Aromatic ring substitution Side chain Alkylation N-Alkylation Ki (nM)
R1 R2 R3 R4 R5 R6
1 -CH3 -H -H -H -H -H 685.70
2A -H -H -H -CH3 -H -H 130
3 -H -H -OCH3 -CH3 -H -H 3.121
4 -H -H -Cl -CH3 -H -H 23.97
5 -H -H -Br -CH3 -H -H 58.78
6 -H -H -H -CH2(CH2)2CH3 -H -H 123.70
7A -H -H -H -CH3 -H -CH3 46
8C -H -H -OCH3 -H -H -CH(CH3)2 50
9 -H -H -H -H -CH3 -CH3 88.49
10A -H -OH -H -H -CH3 -CH3 6
11B -H -H -OH -H -CH3 -CH3 3.5
12A -H -H -OCH3 -H -CH3 -CH3 14
13 -H -OH -H -H -CH3 -CH2CH3 64.8
14C -H -H -H -H -CH3 -CH(CH3)2 38
15C -H -H -OCH3 -H -CH3 -CH(CH3)2 17
16C -H -H -CH3 -H -CH3 -CH(CH3)2 28
17C -H -OH -H -H -CH3 -CH(CH3)2 13
18 -H -OAc -H -H -CH2CH3 -CH2CH3 595.30
19C -H -OH -H -H -CH2CH3 -CH2CH3 14
20 -H -H -OCH3 -H -CH2CH3 -CH2CH2CH3 122.30
21B -H -H -OH -H -CH(CH3)2 -CH(CH3)2 5.6
22D -H -H -H -H -CH2CH=CH2 -CH2CH=CH2 701
23D -H -OAC -H -H -CH2CH=CH2 -CH2CH=CH2 565
24D -H -OH -H -H -CH2CH=CH2 -CH2CH=CH2 652
25 -H -H -OCH3 -H -CH2CH=CH2 -CH2CH=CH2 258.41
26D -CH3 -H -OCH3 -H -CH2CH=CH2 -CH2CH=CH2 1,153
27D -H -H F -H -CH2CH=CH2 -CH2CH=CH2 247
28D -H -H Br -H -CH2CH=CH2 -CH2CH=CH2 477
29D -CH3 -H F -H -CH2CH=CH2 -CH2CH=CH2 655
30D -CH2CH3 -H -H -H -CH2CH=CH2 -CH2CH=CH2 1,515
31A -H -OH -H -H -CH2CH(CH3)2 -CH2CH(CH3)2 260
32A -H -OH -H -H -CH2CH(CH3)CH2CH3 -CH2CH(CH3)CH2CH3 39
33 -H -H -H -H -CH2(CH2)2CH3 -CH2(CH2)2CH3 822.90
34A -H -H -H -H Pyrrolidinyl 110
35A -H -H -H -H Piperidyl 760
36C -H -H -H -H 2,5-dimethylpyrol 2,430
Ketanserin 22.21

AThese were adapted from (Nichols, 2012). BThis was adapted from (Klein et al., 2011). CThese were adapted from (McKenna et al., 1990). DThese were adapted from (Klein et al., 2018).

1. 2-MT.

3. 5-MeO-AMT: 5-methoxy-α-methyltryptamine.

4. 5-CAMT HCl: 5-Chloro-3-(2-aminoethyl)indole Hydrochloride.

5. 5-BAMT HCl: 5-Bromo-3-(2-aminoethyl)indole Hydrochloride.

6. ABT HCl.

9. DMT fumarate: N,N-dimethyl-1H-indole-3-ethanamine, (2E)-2-butenedioate.

13. 4-OH-MET fumarate: 4-hydroxy-N-methyl-N-ethyltryptamine, metocin, or methylcybin.

18. 4-AcO-DET fumarate (1 : 0.83): 4-Acetoxy-N,N-diethyltryptamine.

20. 5-MeO-EPT: 5- methoxy -N-ethyl-N-propyl tryptamine.

25. 5-MeO-DALT: N-allyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl] prop-2-en-1- amine.

33. DBT HCl: 1H-Indole-3-ethanamine, N,N-dibutyl-N,N-Dibutyltryptamin.

Biomolecules & Therapeutics 2023;31:176~182 https://doi.org/10.4062/biomolther.2022.096
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