Histamine trifluoromethyl toluidide

Histamine trifluoromethyl toluidide
Names
IUPAC name
6-[2-(1H-imidazol-5-yl)ethylamino]-N-[4-(trifluoromethyl)phenyl]heptanamide
Other names
HTFMT, HTMT
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C19H25F3N4O/c1-14(24-11-10-17-12-23-13-25-17)4-2-3-5-18(27)26-16-8-6-15(7-9-16)19(20,21)22/h6-9,12-14,24H,2-5,10-11H2,1H3,(H,23,25)(H,26,27) ☒N
    Key: PMKJGGBYYNEYPA-UHFFFAOYSA-N ☒N
  • InChI=1/C19H25F3N4O/c1-14(24-11-10-17-12-23-13-25-17)4-2-3-5-18(27)26-16-8-6-15(7-9-16)19(20,21)22/h6-9,12-14,24H,2-5,10-11H2,1H3,(H,23,25)(H,26,27)
    Key: PMKJGGBYYNEYPA-UHFFFAOYAA
  • FC(F)(F)c1ccc(cc1)NC(=O)CCCCC(NCCc2cnc[nH]2)C
Properties
C19H25F3N4O
Molar mass 382.42321
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Histamine trifluoromethyl toluidide (HTFMT) is a mixed H1/H2 histamine agonist which is significantly more potent than histamine itself.[1]

It also produces additional actions which appear to be independent of histamine receptors.[2][3]

References

  1. ^ Whyment AD, Blanks AM, Lee K, Renaud LP, Spanswick D. Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors. Journal of Neurophysiology. 2006 Apr;95(4):2492-500. PMID 16354729
  2. ^ Qiu R, Melmon KL, Khan MM. Effects of histamine-trifluoromethyl-toluidide derivative (HTMT) on intracellular calcium in human lymphocytes. Journal of Pharmacology and Experimental Therapeutics. 1990 Jun;253(3):1245-52. PMID 2359026
  3. ^ Kim DC, Lee SY, Jun DJ, Kim SH, Lee JH, Hur EM, Baek NI, Kim KT. Inhibition of store-operated calcium entry-mediated superoxide generation by histamine trifluoromethyltoluide independent of histamine receptors. Biochemical Pharmacology. 2005 Nov 25;70(11):1613-22. PMID 16219299