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A facile preparation of 2-aminomethyl-2-tricyclo[3.3.1.11,7]decaneacetic acid hydrochloride 5 (AdGABA) is described. The synthesis of AdGABA involves the hydrogenation of 2-cyano-2-tricyclo[3.3.1.11,7]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 wit the a2d 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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This page is a summary of: The novel GABA adamantane derivative (AdGABA): design, synthesis, and activity relationship with gabapentin, Bioorganic & Medicinal Chemistry, April 2005, Elsevier,
DOI: 10.1016/j.bmc.2005.02.030.
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