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Histamine trifluoromethyl toluidide

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Histamine trifluoromethyl toluidide
Names

IUPAC name 6-[2-(1H-imidazol-5-yl)ethylamino]-N-[4-(trifluoromethyl)phenyl]heptanamide
Other names HTFMT, HTMT
Identifiers
CAS Number	103827-16-3^Y
3D model (JSmol)	Interactive image
ChemSpider	111155^N
IUPHAR/BPS	1273
PubChem CID	124846
CompTox Dashboard(EPA)	DTXSID70908620
InChI 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
SMILES FC(F)(F)c1ccc(cc1)NC(=O)CCCCC(NCCc2cnc[nH]2)C
Properties
Chemical formula	C₁₉H₂₅F₃N₄O
Molar mass	382.42321
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Histamine trifluoromethyl toluidide (HTFMT) is a mixedH₁/H₂ histamine agonist which is significantly more potent thanhistamine itself.^[1]

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

^Whyment, AD; Blanks, AM; Lee, K; Renaud, LP; Spanswick, D (Apr 2006). "Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors".Journal of Neurophysiology.95 (4):2492–500.doi:10.1152/jn.01135.2004.PMID 16354729.
^Qiu, R; Melmon, KL; Khan, MM (Jun 1990). "Effects of histamine-trifluoromethyl-toluidide derivative (HTMT) on intracellular calcium in human lymphocytes".Journal of Pharmacology and Experimental Therapeutics.253 (3):1245–52.doi:10.1016/S0022-3565(25)13228-X.PMID 2359026.
^Kim, DC; Lee, SY; Jun, DJ; Kim, SH; Lee, JH; Hur, EM; Baek, NI; Kim, KT (Nov 2005). "Inhibition of store-operated calcium entry-mediated superoxide generation by histamine trifluoromethyltoluide independent of histamine receptors".Biochemical Pharmacology.70 (11):1613–22.doi:10.1016/j.bcp.2005.09.001.PMID 16219299.

Agonists

Antagonists

Agonists	Amthamine Betazole Dimaprit Histamine HTMT Impromidine L-Histidine UR-AK49
Antagonists	Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine Lamtidine Lavoltidine (loxtidine) Lupitidine Metiamide Mifentidine Niperotidine Nizatidine Osutidine Oxmetidine Pibutidine Quisultazine (quisultidine) Ramixotidine Ranitidine Roxatidine Sufotidine Tiotidine Tuvatidine Venritidine Xaltidine Zolantidine

Agonists	α-Methylhistamine BP 2.94 Cipralisant (GT-2331) GT-2203 (VUF-5296) Histamine Imetit Immepip Immethridine (BP-1-5375) L-Histidine Methimepip Proxyfan SCH-50971 VUF-5297
Antagonists	A-349821 A-423579 ABT-239 ABT-652 AZD5213 Bavisant Betahistine Burimamide Ciproxifan Clobenpropit Conessine Enerisant GSK-189254 Impentamine Iodophenpropit Irdabisant JNJ-5207852 NNC 38-1049 PF-03654746 Pitolisant SCH-79687 Thioperamide VUF-5681

Agonists	4-Methylhistamine α-Methylhistamine Histamine L-Histidine OUP-16 VUF-8430
Antagonists	JNJ-7777120 Mianserin Seliforant Thioperamide Toreforant VUF-6002

See also: Receptor/signaling modulators; Monoamine metabolism modulators; Monoamine reuptake inhibitors

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