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. 2019 Jan 5;17(1):28. doi: 10.3390/md17010028

Table 1.

Tetrodotoxin (TTX) and analogs shown in Figure 1 and modified from European Food Safety Authority (EFSA) 2017 [45] and Yotsu-Yamasshita et al. (2007) [15,53].

E R1 R2 R3 R4 R5
TTX (*) H OH OH CH2OH OH
4-epiTTX (*) OH H OH CH2OH OH
6-epiTTX (*) H OH CH2OH OH OH
11-deoxyTTX (*) H OH OH CH3 OH
6,11-dideoxyTTX H OH H CH3 OH
8,11-dideoxyTTX H OH OH CH3 H
11-oxoTTX (*) H OH OH CH(OH)2 OH
11-norTTX-6,6-diol H OH OH OH OH
11-norTTX-6(R)-ol (*) H OH H OH OH
11-norTTX-6(S)-ol (*) H OH OH H OH
Chiriquitoxin H OH OH CH(OH)CH(NH3+)COO OH
TTX-8-O-hemisuccinate H OH OH CH2OH OOC(CH2)2COO
TTX-11-carboxylic acid H OH OH COO OH
TTX (*) H OH OH CH2OH OH
F R1 R2 R3 R4 R5 R6
5-deoxyTTX(*) OH CH2OH H H OH H
5,11-dideoxyTTX (*) OH CH3 H H OH H
5,6,11-trideoxyTTX (*) H CH3 H H OH H
8-epi-5,6,11-trideoxyTTX H CH3 H H H OH
G R1 R2
4,9-anhydro-5,6,11-trideoxyTTX H OH
4.9-anhydro-8-epi-5,6,11-trideoxyTTX OH H
H R1 R2 R3 R4 R5
1-hydroxy-8-epi-5,6,11-trideoxyTTX OH H OH OH H
4-epi-5,6,11-trideoxyTTX H OH H H OH
I R1 R2 R3
4,4a-anhydro-5,6,11-trideoxyTTX H OH H
1-hydroxy-4,4a-anhydro-8-epi-5,5,11-trideooxyTTX OH H OH