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Comparative Study
. 2005 Apr 15;13(8):2791-8.
doi: 10.1016/j.bmc.2005.02.030.

The novel GABA adamantane derivative (AdGABA): design, synthesis, and activity relationship with gabapentin

Grigoris Zoidis  1 , Ioannis Papanastasiou, Ioannis Dotsikas, Alejandro Sandoval, Raquel Gouvea Dos Santos, Zeta Papadopoulou-Daifoti, Alexander Vamvakides, Nicolas Kolocouris, Ricardo Felix
Affiliations
Comparative Study

The novel GABA adamantane derivative (AdGABA): design, synthesis, and activity relationship with gabapentin

Grigoris Zoidis et al. Bioorg Med Chem. .

Abstract

A facile preparation of 2-aminomethyl-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid hydrochloride 5 (AdGABA) is described. The synthesis of AdGABA involves the hydrogenation of 2-cyano-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid 11, which was synthesized by two different synthetic routes. AdGABA was found to antagonize the pentylenetetrazole (PTZ) and semicarbazide (SCZ) induced tonic convulsions and exhibits analgesic activity in the hot plate test on mice. Although its mechanism of action is quite similar to that proposed previously for gabapentin (interaction with the alpha2delta subunit of the voltage gated Ca2+ channels), further studies were undertaken in order to clarify the precise mechanism of the anticonvulsant and analgesic effects of AdGABA on a molecular level.

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