Proxyfan

Proxyfan is a histamine H₃ receptor ligand which is a "protean agonist", producing different effects ranging from full agonist, to antagonist, to inverse agonist in different tissues, depending on the level of constitutive activity of the histamine H₃ receptor. This gives it a complex activity profile in vivo which has proven useful for scientific research.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

Quick facts Names, Identifiers ...

Proxyfan
Names

Preferred IUPAC name 4-[3-(Benzyloxy)propyl]-1H-imidazole
Identifiers
CAS Number	177708-09-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:93359
ChEMBL	ChEMBL19173
ChemSpider	4927056
IUPHAR/BPS	1255
PubChem CID	6421522
UNII	2F2S8PT5HN
CompTox Dashboard (EPA)	DTXSID00849491
InChI InChI=1S/C13H16N2O/c1-2-5-12(6-3-1)10-16-8-4-7-13-9-14-11-15-13/h1-3,5-6,9,11H,4,7-8,10H2,(H,14,15) Key: WNWALBVQAAIULR-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)COCCCC2=CN=CN2
Properties
Chemical formula	C₁₃H₁₆N₂O
Molar mass	216.284 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

[1]
Morisset, S.; Rouleau, A.; Ligneau, X.; Gbahou, F.; Tardivel-Lacombe, J.; Stark, H.; Schunack, W.; Ganellin, C. R.; Schwartz, J. C.; Arrang, J. M. (2000). "High constitutive activity of native H3 receptors regulates histamine neurons in brain". Nature. 408 (6814): 860–864. doi:10.1038/35048583. PMID 11130725.
[2]
Fox, G. B.; Pan, J. B.; Esbenshade, T. A.; Bitner, R. S.; Nikkel, A. L.; Miller, T.; Kang, C. H.; Bennani, Y. L.; Black, L. A.; Faghih, R.; Hancock, A. A.; Decker, M. W. (2002). "Differential in vivo effects of H3 receptor ligands in a new mouse dipsogenia model". Pharmacology, Biochemistry, and Behavior. 72 (3): 741–750. doi:10.1016/s0091-3057(02)00745-1. PMID 12175472.
[3]
Gbahou, F.; Rouleau, A.; Morisset, S.; Parmentier, R.; Crochet, S.; Lin, J. S.; Ligneau, X.; Tardivel-Lacombe, J.; Stark, H.; Schunack, W.; Ganellin, C. R.; Schwartz, J. C.; Arrang, J. M. (2003). "Protean agonism at histamine H3 receptors in vitro and in vivo". Proceedings of the National Academy of Sciences of the United States of America. 100 (19): 11086–11091. doi:10.1073/pnas.1932276100. PMC 196931. PMID 12960366.
[4]
Baldi, E.; Bucherelli, C.; Schunack, W.; Cenni, G.; Blandina, P.; Passani, M. B. (2005). "The H3 receptor protean agonist proxyfan enhances the expression of fear memory in the rat". Neuropharmacology. 48 (2): 246–251. doi:10.1016/j.neuropharm.2004.09.009. hdl:2158/220558. PMID 15695163.
[5]
Krueger, Kathleen M.; Witte, David G.; Ireland-Denny, Lynne; Miller, Thomas R.; Baranowski, John L.; Buckner, Steve; Milicic, Ivan; Esbenshade, Timothy A.; Hancock, Arthur A. (2005). "G Protein-Dependent Pharmacology of Histamine H₃ Receptor Ligands: Evidence for Heterogeneous Active State Receptor Conformations". Journal of Pharmacology and Experimental Therapeutics. 314 (1): 271–281. doi:10.1124/jpet.104.078865. PMID 15821027.
[6]
Arrang, J. M.; Morisset, S.; Gbahou, F. (2007). "Constitutive activity of the histamine H3 receptor". Trends in Pharmacological Sciences. 28 (7): 350–357. doi:10.1016/j.tips.2007.05.002. PMID 17573125.
[7]
Baker, Jillian G. (2008). "Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells". BMC Pharmacology. 8 9. doi:10.1186/1471-2210-8-9. PMC 2430196. PMID 18538007.

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