40546-47-2
Chemical Structure
Imbutamine
- CAS No.: 40546-47-2
- Formula:C7H13N3
- Molecular Weight:139.20
InChIKey: VJSUMPPMFYQOMP-UHFFFAOYSA-N
SMILES: NCCCCC1=CN=CN1
Biological Activity: Imbutamine is a histamine H3 receptor (H3R) agonist that activates the GPCR regulating neurotransmitter release. Imbutamine binds to human H3R with a pKi of 8.4 and a Ki of 4.27 nM, activates human H3R-mediated G protein signaling with an EC50 of 3.13 nM, and exhibits near-full intrinsic agonist activity. Imbutamine is more selective for human H3R than for human H4R, activates human H4R-mediated G protein signaling with an EC50 of 66.1 nM, and binds to human H4R with a Ki of 12.7 nM[1][2][3][4][5][6].
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Imbutamine | Imbutamine is a histamine H3 receptor (H3R) agonist that activates the GPCR regulating neurotransmitter release. Imbutamine binds to human H3R with a pKi of 8.4 and a Ki of 4.27 nM, activates human H3R-mediated G protein signaling with an EC50 of 3.13 nM, and exhibits near-full intrinsic agonist activity. Imbutamine is more selective for human H3R than for human H4R, activates human H4R-mediated G protein signaling with an EC50 of 66.1 nM, and binds to human H4R with a Ki of 12.7 nM. | |||||||||||||||||||||
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References
- [1]. Wágner G, et al. 4-(3-Aminoazetidin-1-yl)pyrimidin-2-amines as High-Affinity Non-imidazole Histamine H Receptor Agonists with in Vivo Central Nervous System Activity. Journal of medicinal chemistry. 2019 Dec 12;62(23):10848-10866.
- [2]. Kitbunnadaj R, et al. New high affinity H3 receptor agonists without a basic side chain. Bioorganic & medicinal chemistry. 2005 Dec 01;13(23):6309-23.
- [3]. Govoni M, et al. A chemical switch for the modulation of the functional activity of higher homologues of histamine on the human histamine H3 receptor: effect of various substitutions at the primary amino function. Journal of medicinal chemistry. 2006 Apr 20;49(8):2549-57.
- [4]. Rahman SN, et al. Structural and Molecular Determinants for Isoform Bias at Human Histamine H Receptor Isoforms. ACS chemical neuroscience. 2023 Feb 15;14(4):645-656.
- [5]. Geyer R, et al. Conformational Restriction and Enantioseparation Increase Potency and Selectivity of Cyanoguanidine-Type Histamine H4 Receptor Agonists. Journal of medicinal chemistry. 2016 Apr 14;59(7):3452-70. [Content Brief]
- [6]. Geyer R, et al. Synthesis and functional characterization of imbutamine analogs as histamine H3 and H4 receptor ligands. Archiv der Pharmazie. 2014 Feb;347(2):77-88.
