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Four pairs of novel dopamine enantiomer trimers, (±)-cryptamides A–D (<b>1</b>–<b>4</b>), and 10 pairs of previously described dopamine enantiomer dimers (<b>5</b>–<b>14</b>) were isolated from the Periostracum cicadae, the cast-off shell of the insect <i>Cryptotympana pustulata</i>. Aside from being pairs of enantiomers, the eight trimers were also elucidated to be regioisomers, most likely resulting from their mechanism of formation, [4 + 2] cycloaddition. The discovery of dopamine trimers is rarely reported when it comes to natural products derived from insects.