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MedKoo Cat#: 561742 | Name: rac-BHFF
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

rac-BHFF is a selective GABAB receptor agonist. rac-BHFF has been studied for its ability to relief neuropathic pain induced by chronic constriction of the sciatic nerve in mice.

Chemical Structure

rac-BHFF
rac-BHFF
CAS#123557-91-5

Theoretical Analysis

MedKoo Cat#: 561742

Name: rac-BHFF

CAS#: 123557-91-5

Chemical Formula: C17H21F3O3

Exact Mass: 330.1443

Molecular Weight: 330.34

Elemental Analysis: C, 61.81; H, 6.41; F, 17.25; O, 14.53

Price and Availability

Size Price Availability Quantity
5mg USD 285.00 2 Weeks
10mg USD 450.00 2 Weeks
25mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
rac-BHFF; rac BHFF; racBHFF;
IUPAC/Chemical Name
5,7-di-tert-butyl-3-hydroxy-3-(trifluoromethyl)benzofuran-2(3H)-one
InChi Key
RVNOANDLZIIFHB-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H21F3O3/c1-14(2,3)9-7-10(15(4,5)6)12-11(8-9)16(22,13(21)23-12)17(18,19)20/h7-8,22H,1-6H3
SMILES Code
O=C1OC2=C(C(C)(C)C)C=C(C(C)(C)C)C=C2C1(O)C(F)(F)F
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 330.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Colombo G. Positive allosteric modulators of the GABAB receptor: a new class of ligands with therapeutic potential for alcohol use disorder. Alcohol Alcohol. 2024 Mar 16;59(3):agae018. doi: 10.1093/alcalc/agae018. PMID: 38566580. 2: Mugnaini C, Brizzi A, Mostallino R, Castelli MP, Corelli F. Structure optimization of positive allosteric modulators of GABAB receptors led to the unexpected discovery of antagonists/potential negative allosteric modulators. Bioorg Med Chem Lett. 2020 Sep 15;30(18):127443. doi: 10.1016/j.bmcl.2020.127443. Epub 2020 Jul 28. PMID: 32730942. 3: de Miguel E, Vekovischeva O, Kuokkanen K, Vesajoki M, Paasikoski N, Kaskinoro J, Myllymäki M, Lainiola M, Janhunen SK, Hyytiä P, Linden AM, Korpi ER. GABAB receptor positive allosteric modulators with different efficacies affect neuroadaptation to and self-administration of alcohol and cocaine. Addict Biol. 2019 Nov;24(6):1191-1203. doi: 10.1111/adb.12688. Epub 2018 Nov 13. PMID: 30421860. 4: Xia S, He C, Zhu Y, Wang S, Li H, Zhang Z, Jiang X, Liu J. GABABR-Induced EGFR Transactivation Promotes Migration of Human Prostate Cancer Cells. Mol Pharmacol. 2017 Sep;92(3):265-277. doi: 10.1124/mol.116.107854. Epub 2017 Apr 19. PMID: 28424220. 5: Zemoura K, Ralvenius WT, Malherbe P, Benke D. The positive allosteric GABAB receptor modulator rac-BHFF enhances baclofen-mediated analgesia in neuropathic mice. Neuropharmacology. 2016 Sep;108:172-8. doi: 10.1016/j.neuropharm.2016.04.028. Epub 2016 Apr 22. PMID: 27108932. 6: Brown JW, Moeller A, Schmidt M, Turner SC, Nimmrich V, Ma J, Rueter LE, van der Kam E, Zhang M. Anticonvulsant effects of structurally diverse GABA(B) positive allosteric modulators in the DBA/2J audiogenic seizure test: Comparison to baclofen and utility as a pharmacodynamic screening model. Neuropharmacology. 2016 Feb;101:358-69. doi: 10.1016/j.neuropharm.2015.10.009. Epub 2015 Oct 22. PMID: 26471422. 7: Pozdnyakova N, Dudarenko M, Borisova T. New effects of GABAB receptor allosteric modulator rac-BHFF on ambient GABA, uptake/release, Em and synaptic vesicle acidification in nerve terminals. Neuroscience. 2015 Sep 24;304:60-70. doi: 10.1016/j.neuroscience.2015.07.037. Epub 2015 Jul 18. PMID: 26197223. 8: Maccioni P, Vargiolu D, Thomas AW, Malherbe P, Mugnaini C, Corelli F, Leite- Morris KA, Gessa GL, Colombo G. Inhibition of alcohol self-administration by positive allosteric modulators of the GABAB receptor in rats: lack of tolerance and potentiation of baclofen. Psychopharmacology (Berl). 2015 May;232(10):1831-41. doi: 10.1007/s00213-014-3815-8. Epub 2014 Nov 26. PMID: 25420609. 9: Frau R, Bini V, Pillolla G, Malherbe P, Pardu A, Thomas AW, Devoto P, Bortolato M. Positive allosteric modulation of GABAB receptors ameliorates sensorimotor gating in rodent models. CNS Neurosci Ther. 2014 Jul;20(7):679-84. doi: 10.1111/cns.12261. Epub 2014 Apr 7. PMID: 24703381; PMCID: PMC4062587. 10: Koek W, Cheng K, Rice KC. Discriminative stimulus effects of the GABAB receptor-positive modulator rac-BHFF: comparison with GABAB receptor agonists and drugs of abuse. J Pharmacol Exp Ther. 2013 Mar;344(3):553-60. doi: 10.1124/jpet.112.202226. Epub 2012 Dec 28. PMID: 23275067; PMCID: PMC3583500. 11: Loi B, Maccioni P, Lobina C, Carai MA, Gessa GL, Thomas AW, Malherbe P, Colombo G. Reduction of alcohol intake by the positive allosteric modulator of the GABA(B) receptor, rac-BHFF, in alcohol-preferring rats. Alcohol. 2013 Feb;47(1):69-73. doi: 10.1016/j.alcohol.2012.11.002. Epub 2012 Dec 6. PMID: 23218664. 12: Koek W, France CP, Cheng K, Rice KC. Effects of the GABAB receptor-positive modulators CGP7930 and rac-BHFF in baclofen- and γ-hydroxybutyrate- discriminating pigeons. J Pharmacol Exp Ther. 2012 May;341(2):369-76. doi: 10.1124/jpet.111.190975. Epub 2012 Feb 7. PMID: 22319197; PMCID: PMC3336808. 13: Hensler JG, Advani T, Burke TF, Cheng K, Rice KC, Koek W. GABAB receptor- positive modulators: brain region-dependent effects. J Pharmacol Exp Ther. 2012 Jan;340(1):19-26. doi: 10.1124/jpet.111.186577. Epub 2011 Sep 27. PMID: 21954301; PMCID: PMC3251019. 14: Gannon RL, Millan MJ. Positive allosteric modulators at GABAB receptors exert intrinsic actions and enhance the influence of baclofen on light-induced phase shifts of hamster circadian activity rhythms. Pharmacol Biochem Behav. 2011 Oct;99(4):712-7. doi: 10.1016/j.pbb.2011.06.029. Epub 2011 Jul 6. PMID: 21756929. 15: Koek W, France CP, Cheng K, Rice KC. GABAB receptor-positive modulators: enhancement of GABAB receptor agonist effects in vivo. J Pharmacol Exp Ther. 2010 Oct;335(1):163-71. doi: 10.1124/jpet.110.171116. Epub 2010 Jul 13. PMID: 20628000; PMCID: PMC2957789. 16: Maccioni P, Thomas AW, Carai MA, Gessa GL, Malherbe P, Colombo G. The positive allosteric modulator of the GABA(B) receptor, rac-BHFF, suppresses alcohol self-administration. Drug Alcohol Depend. 2010 Jun 1;109(1-3):96-103. doi: 10.1016/j.drugalcdep.2009.12.019. Epub 2010 Jan 20. PMID: 20089372. 17: Malherbe P, Masciadri R, Norcross RD, Knoflach F, Kratzeisen C, Zenner MT, Kolb Y, Marcuz A, Huwyler J, Nakagawa T, Porter RH, Thomas AW, Wettstein JG, Sleight AJ, Spooren W, Prinssen EP. Characterization of (R,S)-5,7-di-tert- butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one as a positive allosteric modulator of GABAB receptors. Br J Pharmacol. 2008 Jun;154(4):797-811. doi: 10.1038/bjp.2008.135. Epub 2008 Apr 21. PMID: 18536733; PMCID: PMC2439845.