histamine   Click here for help

GtoPdb Ligand ID: 1204

PDB Ligand Immunopharmacology Ligand
Comment: Histamine is a potent pro-inflammatory mediator that is principally released from mast cells. It is also involved in regulating physiological function in the gut, and acts as a neurotransmitter.
Histamine activates carbonic anhydrases, and is most potent at the CA5A and CA1 isoforms (KA values 10 and 2100 nM respectively) [21].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 54.7
Molecular weight 111.08
XLogP -0.75
No. Lipinski's rules broken 0
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Canonical SMILES NCCc1cnc[nH]1
Isomeric SMILES NCCc1cnc[nH]1
InChI InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
1. Beukers MW, Klaassen CH, De Grip WJ, Verzijl D, Timmerman H, Leurs R. (1997)
Heterologous expression of rat epitope-tagged histamine H2 receptors in insect Sf9 cells.
Br J Pharmacol, 122 (5): 867-74. [PMID:9384502]
2. Booth RG, Moniri NH, Bakker RA, Choksi NY, Nix WB, Timmerman H, Leurs R. (2002)
A novel phenylaminotetralin radioligand reveals a subpopulation of histamine H(1) receptors.
J Pharmacol Exp Ther, 302 (1): 328-36. [PMID:12065734]
3. Chen J, Liu C, Lovenberg TW. (2003)
Molecular and pharmacological characterization of the mouse histamine H3 receptor.
Eur J Pharmacol, 467 (1-3): 57-65. [PMID:12706455]
4. Cogé F, Guénin SP, Audinot V, Renouard-Try A, Beauverger P, Macia C, Ouvry C, Nagel N, Rique H, Boutin JA et al.. (2001)
Genomic organization and characterization of splice variants of the human histamine H3 receptor.
Biochem J, 355 (Pt 2): 279-88. [PMID:11284713]
5. Engel K, Wang J. (2005)
Interaction of organic cations with a newly identified plasma membrane monoamine transporter.
Mol Pharmacol, 68 (5): 1397-407. [PMID:16099839]
6. Erickson JD, Schafer MK, Bonner TI, Eiden LE, Weihe E. (1996)
Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter.
Proc Natl Acad Sci USA, 93 (10): 5166-71. [PMID:8643547]
7. Gbahou F, Vincent L, Humbert-Claude M, Tardivel-Lacombe J, Chabret C, Arrang JM. (2006)
Compared pharmacology of human histamine H3 and H4 receptors: structure-activity relationships of histamine derivatives.
Br J Pharmacol, 147 (7): 744-54. [PMID:16432504]
8. Gründemann D, Liebich G, Kiefer N, Köster S, Schömig E. (1999)
Selective substrates for non-neuronal monoamine transporters.
Mol Pharmacol, 56 (1): 1-10. [PMID:10385678]
9. Kitbunnadaj R, Zuiderveld OP, De Esch IJ, Vollinga RC, Bakker R, Lutz M, Spek AL, Cavoy E, Deltent MF, Menge WM et al.. (2003)
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
J Med Chem, 46 (25): 5445-57. [PMID:14640553]
10. Ligneau X, Morisset S, Tardivel-Lacombe J, Gbahou F, Ganellin CR, Stark H, Schunack W, Schwartz JC, Arrang JM. (2000)
Distinct pharmacology of rat and human histamine H(3) receptors: role of two amino acids in the third transmembrane domain.
Br J Pharmacol, 131 (7): 1247-50. [PMID:11090094]
11. Lim HD, van Rijn RM, Ling P, Bakker RA, Thurmond RL, Leurs R. (2005)
Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.
J Pharmacol Exp Ther, 314 (3): 1310-21. [PMID:15947036]
12. Liu C, Ma X, Jiang X, Wilson SJ, Hofstra CL, Blevitt J, Pyati J, Li X, Chai W, Carruthers N et al.. (2001)
Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.
Mol Pharmacol, 59 (3): 420-6. [PMID:11179434]
13. Liu C, Wilson SJ, Kuei C, Lovenberg TW. (2001)
Comparison of human, mouse, rat, and guinea pig histamine H4 receptors reveals substantial pharmacological species variation.
J Pharmacol Exp Ther, 299 (1): 121-30. [PMID:11561071]
14. Lovenberg TW, Pyati J, Chang H, Wilson SJ, Erlander MG. (2000)
Cloning of rat histamine H(3) receptor reveals distinct species pharmacological profiles.
J Pharmacol Exp Ther, 293 (3): 771-8. [PMID:10869375]
15. Moguilevsky N, Varsalona F, Noyer M, Gillard M, Guillaume JP, Garcia L, Szpirer C, Szpirer J, Bollen A. (1994)
Stable expression of human H1-histamine-receptor cDNA in Chinese hamster ovary cells. Pharmacological characterisation of the protein, tissue distribution of messenger RNA and chromosomal localisation of the gene.
Eur J Biochem, 224 (2): 489-95. [PMID:7925364]
16. Morisset S, Sasse A, Gbahou F, Héron A, Ligneau X, Tardivel-Lacombe J, Schwartz JC, Arrang JM. (2001)
The rat H3 receptor: gene organization and multiple isoforms.
Biochem Biophys Res Commun, 280 (1): 75-80. [PMID:11162480]
17. Morse KL, Behan J, Laz TM, West Jr RE, Greenfeder SA, Anthes JC, Umland S, Wan Y, Hipkin RW, Gonsiorek W et al.. (2001)
Cloning and characterization of a novel human histamine receptor.
J Pharmacol Exp Ther, 296 (3): 1058-66. [PMID:11181941]
18. Ratnala VR, Swarts HG, VanOostrum J, Leurs R, DeGroot HJ, Bakker RA, DeGrip WJ. (2004)
Large-scale overproduction, functional purification and ligand affinities of the His-tagged human histamine H1 receptor.
Eur J Biochem, 271 (13): 2636-46. [PMID:15206929]
19. Rouleau A, Héron A, Cochois V, Pillot C, Schwartz JC, Arrang JM. (2004)
Cloning and expression of the mouse histamine H3 receptor: evidence for multiple isoforms.
J Neurochem, 90 (6): 1331-8. [PMID:15341517]
20. Seifert R, Wenzel-Seifert K, Burckstummer T, Pertz HH, Schunack W, Dove S, Buschauer A, Elz S. (2003)
Multiple differences in agonist and antagonist pharmacology between human and guinea pig histamine H1-receptor.
J Pharmacol Exp Ther, 305 (3): 1104-15. [PMID:12626648]
21. Tanini D, Capperucci A, Supuran CT, Angeli A. (2019)
Sulfur, selenium and tellurium containing amines act as effective carbonic anhydrase activators.
Bioorg Chem, 87: 516-522. [PMID:30928874]
22. Terzioglu N, van Rijn RM, Bakker RA, De Esch IJ, Leurs R. (2004)
Synthesis and structure-activity relationships of indole and benzimidazole piperazines as histamine H(4) receptor antagonists.
Bioorg Med Chem Lett, 14 (21): 5251-6. [PMID:15454206]
23. Wang J. (2016)
The plasma membrane monoamine transporter (PMAT): Structure, function, and role in organic cation disposition.
Clin Pharmacol Ther, 100 (5): 489-499. [PMID:27506881]
24. Wulff BS, Hastrup S, Rimvall K. (2002)
Characteristics of recombinantly expressed rat and human histamine H3 receptors.
Eur J Pharmacol, 453 (1): 33-41. [PMID:12393057]
25. Xie SX, Ghorai P, Ye QZ, Buschauer A, Seifert R. (2006)
Probing ligand-specific histamine H1- and H2-receptor conformations with NG-acylated Imidazolylpropylguanidines.
J Pharmacol Exp Ther, 317 (1): 139-46. [PMID:16394198]
26. Zhu Y, Michalovich D, Wu H, Tan KB, Dytko GM, Mannan IJ, Boyce R, Alston J, Tierney LA, Li X et al.. (2001)
Cloning, expression, and pharmacological characterization of a novel human histamine receptor.
Mol Pharmacol, 59 (3): 434-41. [PMID:11179436]