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. Author manuscript; available in PMC: 2015 Oct 1.
Published in final edited form as: Psychopharmacology (Berl). 2014 May 7;231(21):4135–4144. doi: 10.1007/s00213-014-3557-7

Table 1.

DAT, SERT, and NET-mediated Releasing Properties and 5-HT2A, 5-HT2A β-arrestin, and 5-HT1A Activity of Psychedelic Tryptamine Analogs

graphic file with name nihms593012t1.jpg
Release EC50, (nM)a 5-HT2Ab 5-HT1Ab 5-HT2A β-arrestinc
# Name X R1 R2 R3 DAT SERT NET EC50,
(nM)		 Emax,
(%)		 EC50,
(nM)		 Emax,
(%)		 EC50, (nM) Emax,
(%)		 Psychoactive
Effectse
12 T H H H H 164 ± 16 32.6 ± 2.6 716 ± 46 7.36 ± 0.56 104 ± 4 IA 3485 ± 234 108 ± 16 Psychoactive, short acting due to metabolism, increased blood pressure, similar to LSD
13 AMT H H H Me 78.6 ± 4.0 21.7 ± 1.0 112 ± 6 23.1 ± 2.4 103 ± 3 IA 4855 ± 1416 95 ± 17 Psychedelic but varied, fast/slow onset, good/bad experiences, long lasting, no visuals, speed-like, tachycardia, jaw clenching
14 NMT H Me H H 321 ± 23 22.4 ± 1.4 733 ± 94 50.7 ± 7.1 96 ± 2 IA IA NR
15 NETPg H Et H H 6660 ± 551 18.6 ± 1.6 3862 ± 635d 38.3 ± 2.7 99 ± 2 IA 4582f 64f NR
6 DMT H Me Me H >10,000 114 ± 15 4166 ± 317 38.3 ± 0.81 83 ± 0.4 IA IA Heavy intoxicant and hallucinogen, visuals, intense colors
16 Dimethyl - serotonin OH Me Me H >10,000 30.5 ± 8.6 >10,000 3.49 ± 0.08 100 ± 2 366 ± 67 95 ± 1 ND Some visuals (lines and dots), tightness in chest, nausea, breathing issues, mind feels crowded
17 5MeO-NMT OMe Me H H >10,000 1114 ± 700 >10,000 3.78 ± 0.73 84 ± 20 220 ± 12 72 ± 4 611 ± 149 66 ± 9 NR
18 5MeO-NET OMe Et H H >10,000 284 ± 41.6 >10,000 1.92 ± 0.29 112 ± 3 262 ± 27 70 ± 7 568 ± 174 103 ± 12 NR

IA = Inactive at 10 µM in agonist screen.

NR = Not reported in TiHKAL.

ND = Not determined.

a

Release EC50 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

IC50 for uptake inhibition.

e

Tabulated from anecdotal reports in TiHKAL.

f

Single determination.

g

This compound is referred to as “NET” in TiHKAL but was altered to avoid confusion with the norepinephrine transporter.