4-DAMP

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4-DAMP
4-DAMP.svg
4-DAMP-3D-balls-by-AHRLS-2012.png
Names
Preferred IUPAC name
4-[(Diphenylacetyl)oxy]-1,1-dimethylpiperidin-1-ium iodide
Other names
4-(2,2-Diphenylacetoxy)-1,1-dimethylpiperidin-1-ium iodide
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C21H26NO2.HI/c1-22(2)15-13-19(14-16-22)24-21(23)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18;/h3-12,19-20H,13-16H2,1-2H3;1H/q+1;/p-1
    Key: WWJHRSCUAQPFQO-UHFFFAOYSA-M
  • [I-].C[N+]1(C)CCC(CC1)OC(=O)C(C1=CC=CC=C1)C1=CC=CC=C1
Properties
C21H26INO2
Molar mass 451.348 g·mol−1
Appearance White to beige powder[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-DAMP (1,1-dimethyl-4-diphenylacetoxypiperidinium iodide) is a selective muscarinic acetylcholine receptor (mAChR) M3 antagonist.[2] It is also able to antagonize M1 receptors but "prefers" M3.[3][4] It competitively binds to the acetylcholine binding site on mAChRs, causing right-ward shift in the dose response curves for mAChR agonists.

References

  1. ^ "4-DAMP". Sigma-Aldrich.
  2. ^ Zhu, MH; Sung, IK; Zheng, H; Sung, TS; Britton, FC; O'Driscoll, K; Koh, SD; Sanders, KM (2011). "Muscarinic activation of Ca2+-activated Cl- current in interstitial cells of Cajal". J Physiol. 589 (Pt18): 4565–4582. doi:10.1113/jphysiol.2011.211094. PMC 3208225. PMID 21768263.
  3. ^ Teixeira-Neto, FJ; McDonell, WN; Black, WD; Harris, W and; Grovum, L (2012). "Effects of muscarinic receptor antagonists on acetylcholine-induced contractions of jejunal smooth muscle in horses". Journal of Veterinary Pharmacology and Therapeutics. 35 (4): 313–318. doi:10.1111/j.1365-2885.2011.01330.x. PMID 21859432.
  4. ^ Greenwood, JM and; Dragunow, M (2010). "M3 muscarinic receptors promote cell survival through activation of the extracellular regulated kinase (ERK1/2) pathway". Eur J Pharmacol. 640 (1–3): 38–45. doi:10.1016/j.ejphar.2010.05.013. PMID 20519144.