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 |