CGP-7930

CGP-7930 was the first positive allosteric modulator of GABA_B receptors described in literature.^[1][2][3][4] CGP7930 is also a GABA_A receptor positive allosteric modulator and a blocker of Potassium channels.^[5]

CGP-7930

Identifiers
IUPAC name 2,6-Di-tert-butyl-4-(3-hydroxy-2,2-dimethyl-propyl)-phenol
CAS Number	57717-80-3
PubChem CID	5024764
IUPHAR/BPS	1079
ChemSpider	4203613 N
UNII	ZAM4WWA5Y4
CompTox Dashboard (EPA)	DTXSID90407620
Chemical and physical data
Formula	C19H32O2
Molar mass	292.463 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)(C)c1cc(CC(C)(C)CO)cc(C(C)(C)C)c1O
InChI InChI=1S/C19H32O2/c1-17(2,3)14-9-13(11-19(7,8)12-20)10-15(16(14)21)18(4,5)6/h9-10,20-21H,11-12H2,1-8H3 N Key:XLWJPQQFJNGUPA-UHFFFAOYSA-N N
NY (what is this?)  (verify)

CGP7930 was developed in Novartis and has been used extensively for scientific research. It has anxiolytic effects in animal studies,^[6][7] and has a synergistic effect with GABA_B agonists such as baclofen and GHB,^[8][9] as well as reducing self-administration of alcoholic drinks and cocaine.^[10][11]

CNS Review:^[12]

Synthesis

The chemical synthesis has been described:^[13] Starting material:^[14] Product of first step:^[15][16]

2,6-Di-tert-butylphenol is treated with formaldehyde, base and methanol to give [87-97-8] (2). Base catalyzed reaction with isobutaldehyde gives CGP-13501 (3). Hydride reduction of the aldehyde gives the primary alcohol.

According to Krysin (Russia), 2,6-Di-tert-butylphenol is reacted with Neopentyl glycol with lye in an autoclave. Although 1 step reaction, yield was quoted as merely 15%.^[17]