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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid = 462336838
| verifiedrevid = 462336838
| IUPAC_name = N-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl]-2-methyl-5-[4-(trifluoromethyl)phenyl]-4-pyrimidinamine
| IUPAC_name = N-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl]-2-methyl-5-[4-(trifluoromethyl)phenyl]-4-pyrimidinamine
| image = BHF-177_structure.png
| image = BHF-177 Structure.svg


<!--Clinical data-->
<!--Clinical data-->| tradename =
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
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| pregnancy_category =
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| pregnancy_US = <!-- A / B / C / D / X -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
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| pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
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| legal_status =
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
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| routes_of_administration = <!--Pharmacokinetic data-->
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| legal_status =
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| bioavailability =
⚫
| routes_of_administration =
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| protein_bound =
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| metabolism =
⚫
| elimination_half-life =
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| excretion = <!--Identifiers-->
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| IUPHAR_ligand = 5503
⚫
| CAS_number_Ref = {{cascite|correct|??}}
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| CAS_number = 917896-43-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 73Q4TVR90S
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| ATC_prefix =
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| ATC_suffix =
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| ATC_supplemental =
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| PubChem =
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| DrugBank =
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChemSpiderID = 26286940
⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| StdInChI = 1S/C19H20F3N3/c1-11-23-10-16(13-4-6-15(7-5-13)19(20,21)22)18(24-11)25-17-9-12-2-3-14(17)8-12/h4-7,10,12,14,17H,2-3,8-9H2,1H3,(H,23,24,25)/t12-,14+,17+/m0/s1
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
| StdInChIKey = ADHZHPOKTRHZGT-DXCKQFNASA-N


<!--Pharmacokinetic data-->
<!--Chemical data-->| chemical_formula =
| C = 19
⚫
| bioavailability =
| H = 20
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| protein_bound =
| F = 3
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| metabolism =
| N = 3
⚫
| elimination_half-life =
| smiles = Cc3nc(N[C@@H]2C[C@H]1CC[C@@H]2C1)c(cn3)c4ccc(cc4)C(F)(F)F
| excretion =

⚫
<!--Identifiers-->
⚫
| IUPHAR_ligand = 5503
⚫
| CAS_number_Ref = {{cascite|correct|??}}
⚫
| CAS_number = 917896-43-6
⚫
| ATC_prefix =
⚫
| ATC_suffix =
⚫
| ATC_supplemental =
⚫
| PubChem =
⚫
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫
| DrugBank =
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| ChemSpiderID = 26286940
| InChI = 1/C19H20F3N3/c1-11-23-10-16(13-4-6-15(7-5-13)19(20,21)22)18(24-11)25-17-9-12-2-3-14(17)8-12/h4-7,10,12,14,17H,2-3,8-9H2,1H3,(H,23,24,25)/t12-,14+,17+/m0/s1
| InChIKey = ADHZHPOKTRHZGT-DXCKQFNABE
⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| StdInChI = 1S/C19H20F3N3/c1-11-23-10-16(13-4-6-15(7-5-13)19(20,21)22)18(24-11)25-17-9-12-2-3-14(17)8-12/h4-7,10,12,14,17H,2-3,8-9H2,1H3,(H,23,24,25)/t12-,14+,17+/m0/s1
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
| StdInChIKey = ADHZHPOKTRHZGT-DXCKQFNASA-N

<!--Chemical data-->
| chemical_formula =
| C=19 | H=20 | F=3 | N=3
| molecular_weight = 347.377 g/mol
| smiles = C4CC2CC4CC2Nc1nc(C)ncc1-c3ccc(C(F)(F)F)cc3
}}
}}


'''BHF-177''' is a compound used in scientific research which acts as a [[Allosteric regulation#Pharmacology|positive allosteric modulator]] at the [[GABA B receptor|GABA<sub>B</sub>]] [[Receptor (biochemistry)|receptor]].<ref>{{cite journal | last1 = Guery | first1 = S | last2 = Floersheim | first2 = P | last3 = Kaupmann | first3 = K | last4 = Froestl | first4 = W | title = Syntheses and optimization of new GS39783 analogues as positive allosteric modulators of GABAB receptors | journal = Bioorganic & Medicinal Chemistry Letters | volume = 17 | issue = 22 | pages = 6206–11 | year = 2007 | pmid = 17884493 | pmc = 2278029 | doi = 10.1016/j.bmcl.2007.09.023 }}</ref> It was shown to reduce self-administration of [[nicotine]] in animal studies.<ref name="pmid18445779">{{cite journal |author=Paterson NE, Vlachou S, Guery S, Kaupmann K, Froestl W, Markou A |title=Positive Modulation of GABAB Receptors Decreased Nicotine Self-administration and Counteracted Nicotine-induced Enhancement of Brain Reward Function in Rats |journal=J. Pharmacol. Exp. Ther. |volume=326 |issue=1 |pages=306–14 |year=2008 |pmid=18445779 |doi=10.1124/jpet.108.139204 |url= |pmc=2574924}}</ref>
'''BHF-177''' is a compound used in scientific research which acts as a [[Allosteric regulation#Pharmacology|positive allosteric modulator]] at the [[GABA B receptor|GABA<sub>B</sub>]] [[Receptor (biochemistry)|receptor]].<ref>{{cite journal | vauthors = Guery S, Floersheim P, Kaupmann K, Froestl W | title = Syntheses and optimization of new GS39783 analogues as positive allosteric modulators of GABA B receptors | journal = Bioorganic & Medicinal Chemistry Letters | volume = 17 | issue = 22 | pages = 6206–11 | date = November 2007 | pmid = 17884493 | pmc = 2278029 | doi = 10.1016/j.bmcl.2007.09.023 }}</ref> It was shown to reduce self-administration of [[nicotine]] in animal studies.<ref name="pmid18445779">{{cite journal | vauthors = Paterson NE, Vlachou S, Guery S, Kaupmann K, Froestl W, Markou A | title = Positive modulation of GABA(B) receptors decreased nicotine self-administration and counteracted nicotine-induced enhancement of brain reward function in rats | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 326 | issue = 1 | pages = 306–14 | date = July 2008 | pmid = 18445779 | pmc = 2574924 | doi = 10.1124/jpet.108.139204 }}</ref>


== References ==
== References ==
{{Reflist|2}}
{{Reflist|2}}



{{GABAergics}}
{{GABAergics}}


[[Category:Pyrimidines]]
[[Category:Pyrimidines]]
[[Category:Organofluorides]]
[[Category:Trifluoromethyl compounds]]
[[Category:GABAB receptor positive allosteric modulators]]
[[Category:GABAB receptor positive allosteric modulators]]



{{nervous-system-drug-stub}}
{{nervous-system-drug-stub}}

Latest revision as of 23:04, 1 April 2023

BHF-177
Identifiers
  • N-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl]-2-methyl-5-[4-(trifluoromethyl)phenyl]-4-pyrimidinamine
CAS Number
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H20F3N3
Molar mass347.385 g·mol−1
3D model (JSmol)
  • Cc3nc(N[C@@H]2C[C@H]1CC[C@@H]2C1)c(cn3)c4ccc(cc4)C(F)(F)F
  • InChI=1S/C19H20F3N3/c1-11-23-10-16(13-4-6-15(7-5-13)19(20,21)22)18(24-11)25-17-9-12-2-3-14(17)8-12/h4-7,10,12,14,17H,2-3,8-9H2,1H3,(H,23,24,25)/t12-,14+,17+/m0/s1 checkY
  • Key:ADHZHPOKTRHZGT-DXCKQFNASA-N checkY
  (verify)

BHF-177 is a compound used in scientific research which acts as a positive allosteric modulator at the GABAB receptor.[1] It was shown to reduce self-administration of nicotine in animal studies.[2]

References

[edit]
  1. ^ Guery S, Floersheim P, Kaupmann K, Froestl W (November 2007). "Syntheses and optimization of new GS39783 analogues as positive allosteric modulators of GABA B receptors". Bioorganic & Medicinal Chemistry Letters. 17 (22): 6206–11. doi:10.1016/j.bmcl.2007.09.023. PMC 2278029. PMID 17884493.
  2. ^ Paterson NE, Vlachou S, Guery S, Kaupmann K, Froestl W, Markou A (July 2008). "Positive modulation of GABA(B) receptors decreased nicotine self-administration and counteracted nicotine-induced enhancement of brain reward function in rats". The Journal of Pharmacology and Experimental Therapeutics. 326 (1): 306–14. doi:10.1124/jpet.108.139204. PMC 2574924. PMID 18445779.
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