Article · Wikipedia archive · Last revised Jul 10, 2026

CGP-7930

CGP-7930 was the first positive allosteric modulator of GABAB receptors described in literature. CGP7930 is also a GABAA receptor positive allosteric modulator and a blocker of Potassium channels.

Last revised
Jul 10, 2026
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≈ 3 min
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717 w
Citations
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Wikipedia ↗
CGP-7930
Identifiers
  • 2,6-Di-tert-butyl-4-(3-hydroxy-2,2-dimethyl-propyl)-phenol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H32O2
Molar mass292.463 g·mol−1
3D model (JSmol)
  • CC(C)(C)c1cc(CC(C)(C)CO)cc(C(C)(C)C)c1O
  • 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
 ☒NcheckY (what is this?)  (verify)

CGP-7930 was the first positive allosteric modulator of GABAB receptors described in literature.1234 CGP7930 is also a GABAA receptor positive allosteric modulator and a blocker of Potassium channels.5

CGP7930 was developed in Novartis and has been used extensively for scientific research. It has anxiolytic effects in animal studies,67 and has a synergistic effect with GABAB agonists such as baclofen and GHB,89 as well as reducing self-administration of alcoholic drinks and cocaine.1011

CNS Review:12

Synthesis

The chemical synthesis has been described:13 Starting material:14 Product of first step:1516

source ↗

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.

source ↗

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

See also

See also

References

References

  1. Urwyler S, Mosbacher J, Lingenhoehl K, Heid J, Hofstetter K, Froestl W, et al. (November 2001). "Positive allosteric modulation of native and recombinant gamma-aminobutyric acid(B) receptors by 2,6-Di-tert-butyl-4-(3-hydroxy-2,2-dimethyl-propyl)-phenol (CGP7930) and its aldehyde analog CGP13501". Molecular Pharmacology. 60 (5): 963–71. PMID 11641424.
  2. Binet V, Brajon C, Le Corre L, Acher F, Pin JP, Prézeau L (July 2004). "The heptahelical domain of GABA(B2) is activated directly by CGP7930, a positive allosteric modulator of the GABA(B) receptor". The Journal of Biological Chemistry. 279 (28): 29085–91. doi:10.1074/jbc.M400930200. PMC 2557059. PMID 15126507.
  3. Chen Y, Menendez-Roche N, Sher E (June 2006). "Differential modulation by the GABAB receptor allosteric potentiator 2,6-di-tert-butyl-4-(3-hydroxy-2,2-dimethylpropyl)-phenol (CGP7930) of synaptic transmission in the rat hippocampal CA1 area". The Journal of Pharmacology and Experimental Therapeutics. 317 (3): 1170–7. doi:10.1124/jpet.105.099176. PMID 16507713.
  4. Adams CL, Lawrence AJ. "CGP7930: a positive allosteric modulator of the GABAB receptor". CNS Drug Reviews. 13 (3): 308–16. doi:10.1111/j.1527-3458.2007.00021.x. PMC 6494120. PMID 17894647.
  5. Hannan SB, Penzinger R, Mikute G, Smart TG (July 2023). "CGP7930 - An allosteric modulator of GABABRs, GABAARs and inwardly-rectifying potassium channels" (PDF). Neuropharmacology. 109644. doi:10.1016/j.neuropharm.2023.109644. PMID 37422181.
  6. Frankowska M, Filip M, Przegaliński E. "Effects of GABAB receptor ligands in animal tests of depression and anxiety". Pharmacological Reports. 59 (6): 645–55. PMID 18195453.
  7. Jacobson LH, Cryan JF (April 2008). "Evaluation of the anxiolytic-like profile of the GABAB receptor positive modulator CGP7930 in rodents". Neuropharmacology. 54 (5): 854–62. doi:10.1016/j.neuropharm.2008.01.004. PMID 18328507.
  8. Carai MA, Colombo G, Froestl W, Gessa GL (November 2004). "In vivo effectiveness of CGP7930, a positive allosteric modulator of the GABAB receptor". European Journal of Pharmacology. 504 (3): 213–6. doi:10.1016/j.ejphar.2004.10.008. PMID 15541424.
  9. Parker DA, Marino V, Ong J, Puspawati NM, Prager RH (September 2008). "The CGP7930 analogue 2,6-di-tert-butyl-4-(3-hydroxy-2-spiropentylpropyl)-phenol (BSPP) potentiates baclofen action at GABA(B) autoreceptors". Clinical and Experimental Pharmacology & Physiology. 35 (9): 1113–5. doi:10.1111/j.1440-1681.2008.04948.x. PMID 18430050.
  10. Liang JH, Chen F, Krstew E, Cowen MS, Carroll FY, Crawford D, et al. (April 2006). "The GABA(B) receptor allosteric modulator CGP7930, like baclofen, reduces operant self-administration of ethanol in alcohol-preferring rats". Neuropharmacology. 50 (5): 632–9. doi:10.1016/j.neuropharm.2005.11.011. PMID 16406445.
  11. Filip M, Frankowska M, Przegaliński E (November 2007). "Effects of GABA(B) receptor antagonist, agonists and allosteric positive modulator on the cocaine-induced self-administration and drug discrimination". European Journal of Pharmacology. 574 (2–3): 148–57. doi:10.1016/j.ejphar.2007.07.048. PMID 17698060.
  12. Ong, J., Kerr, D. I. B. (September 2005). "Clinical Potential of GABA B Receptor Modulators". CNS Drug Reviews. 11 (3): 317–334. doi:10.1111/j.1527-3458.2005.tb00049.x.
  13. Kerr, David I. B.; Khalafy, Jabbar; Ong, Jennifer; Perkins, Michael V.; Prager, Rolf H.; Puspawati, Ni Made; Rimaz, Mehdi (2006). "Synthesis and Biological Activity of Allosteric Modulators of GABABReceptors, Part 2. 3-(2,6-Bis-tert-butyl-4-hydroxyphenyl)propanols". Australian Journal of Chemistry. 59 (7): 457. doi:10.1071/CH06164.
  14. Richard Henry Kline, EP0027426 (1983 to The Goodyear Tire & Rubber Company).
  15. Kharasch, M. S.; Joshi, B. S. (November 1957). "Reactions of Hindered Phenols. I. Reactions of 4,4'-Dihydroxy-3,5,3',5'-tetra-tert-butyl Diphenylmethane *". The Journal of Organic Chemistry. 22 (11): 1435–1438. doi:10.1021/jo01362a033.
  16. Rimaz, M.; Khalafy, J.; Badali, M.; Ślepokura, K.; Lis, T.; Souldozi, A.; Ramazani, A.; Joo, S. W. (February 2013). "Single crystal X-ray structure of 2,6-di-tert-butyl-4-(3-(4-chlorophenyl)-4-methyl-4,5-dihydroisoxazol-5-yl)phenol 1,4-dioxane hemisolvate". Journal of Structural Chemistry. 54 (1): 217–222. doi:10.1134/S0022476613010368.
  17. Krysin, A. P.; Pustovskikh, I. I.; Koptyug, V. A. (2010). "Synthesis of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols and the properties of related sulfides". Russian Journal of General Chemistry. 80 (10): 2001–2006. doi:10.1134/S1070363210100208.