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. 2018 Sep 26;7(6):1036–1047. doi: 10.1039/c8tx00187a

Table 1. Compounds shown to elicit thalidomide-like embryopathic effects in the rabbit or non-human primate species.

Name Systematic name Structure Test species and references
dl-Thalidomide (dl-α-phthalimidoglutarimide) [1] 2-(2,6-Dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione graphic file with name c8tx00187a-u1.jpg Cynomolgus monkey27
Rhesus monkey28
Baboon29
Marmoset30
Rabbit31,32
d-Thalidomide (d-α-phthalimidoglutarimide) [2] 2-[(3S)-2,6-dioxopiperidin-3-yl]-1H-isoindole-1,3(2H)-dione graphic file with name c8tx00187a-u2.jpg Rabbit23
l-Thalidomide (l-α-phthalimidoglutarimide) [3] 2-[(3R)-2,6-Dioxopiperidin-3-yl]-1H-isoindole-1,3(2H)-dione graphic file with name c8tx00187a-u3.jpg Rabbit23
dl-3-Aminothalidomide (dl-3-amino-α-phthalimidoglutarimide) [4] 4-Amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione graphic file with name c8tx00187a-u4.jpg Rabbit33
dl-3-Nitrothalidomide (dl-3-nitro-α-phthalimidoglutarimide) [5] 2-(2,6-Dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione graphic file with name c8tx00187a-u5.jpg Rabbit33,34
3-Methylthalidomide (α-phthalimido-3-methylglutarimide) [6] 2-(3-Methyl-2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione graphic file with name c8tx00187a-u6.jpg Marmoset35
N-Methylthalidomide (α-phthalimido-N-methylglutarimide) [7] 2-(1-Methyl-2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione graphic file with name c8tx00187a-u7.jpg Rabbit36
Thalidomide analogue EM12 (2-(2,6-dioxopiperidine-3-yl)-phthalimide) [8] 3-(1-Oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione graphic file with name c8tx00187a-u8.jpg Rhesus monkey38
Marmoset39,40
Rabbit37,38
Thalidomide analogue EM12 S-(–)-enantiomer [9] (3S)-3-(1-Oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione graphic file with name c8tx00187a-u9.jpg Marmoset39,41
Thalidomide analogue EM12 R-(+)-enantiomer [10] (3R)-3-(1-Oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione graphic file with name c8tx00187a-u10.jpg Marmoset39,41
Thalidomide analogue EM136 [11] 3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2yl)piperidine-2-one graphic file with name c8tx00187a-u11.jpg Rabbit37
Thalidomide analogue EM255 [12] 3-(1-Oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2-one graphic file with name c8tx00187a-u12.jpg Rabbit37