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 their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

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

[edit]

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

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Histamine receptor modulators

H1|

| Agonists|

* 2-Pyridylethylamine
* Betahistine
* Histamine
* HTMT
* L-Histidine
* UR-AK49

|

Antagonists|

* First-generation: 4-Methyldiphenhydramine
* Alimemazine
* Antazoline
* Azatadine
* Bamipine
* Benzatropine (benztropine)
* Bepotastine
* Bromazine
* Brompheniramine
* Buclizine
* Captodiame
* Carbinoxamine
* Chlorcyclizine
* Chloropyramine
* Chlorothen
* Chlorphenamine
* Chlorphenoxamine
* Cinnarizine
* Clemastine
* Clobenzepam
* Clocinizine
* Cloperastine
* Cyclizine
* Cyproheptadine
* Dacemazine
* Decloxizine
* Deptropine
* Dexbrompheniramine
* Dexchlorpheniramine
* Dimenhydrinate
* Dimetindene
* Diphenhydramine
* Diphenylpyraline
* Doxylamine
* Embramine
* Etodroxizine
* Etybenzatropine (ethylbenztropine)
* Etymemazine
* Fenethazine
* Flunarizine
* Histapyrrodine
* Homochlorcyclizine
* Hydroxyethylpromethazine
* Hydroxyzine
* Isopromethazine
* Isothipendyl
* Meclozine
* Medrylamine
* Mepyramine (pyrilamine)
* Mequitazine
* Methafurylene
* Methapyrilene
* Methdilazine
* Moxastine
* Orphenadrine
* Oxatomide
* Oxomemazine
* Perlapine
* Phenindamine
* Pheniramine
* Phenyltoloxamine
* Pimethixene
* Piperoxan
* Pipoxizine
* Promethazine
* Propiomazine
* Pyrrobutamine
* Talastine
* Thenalidine
* Thenyldiamine
* Thiazinamium
* Thonzylamine
* Tolpropamine
* Tripelennamine
* Triprolidine

* Second/third-generation: Acrivastine
* Alinastine
* Astemizole
* Azelastine
* Bamirastine
* Barmastine
* Bepiastine
* Bepotastine
* Bilastine
* Cabastinen
* Carebastine
* Cetirizine
* Clemastine
* Clemizole
* Clobenztropine
* Desloratadine
* Dorastine
* Ebastine
* Efletirizine
* Emedastine
* Epinastine
* Fexofenadine
* Flezelastine
* Ketotifen
* Latrepirdine
* Levocabastine
* Levocetirizine
* Linetastine
* Loratadine
* Mapinastine
* Mebhydrolin
* Mizolastine
* Moxastine
* Noberastine
* Octastine
* Olopatadine
* Perastine
* Pibaxizine
* Piclopastine
* Quifenadine (phencarol)
* Rocastine
* Rupatadine
* Setastine
* Sequifenadine (bicarphen)
* Talastine
* Temelastine
* Terfenadine
* Vapitadine
* Zepastine

* Others: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, brilaroxazine, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, ziprasidone, zotepine)
* Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
* Tetracyclic antidepressants (e.g., amoxapine, loxapine, maprotiline, mianserin, mirtazapine, oxaprotiline)
* Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, iprindole, lofepramine, nortriptyline, protriptyline, trimipramine)
* Typical antipsychotics (e.g., chlorpromazine, flupenthixol, fluphenazine, loxapine, perphenazine, prochlorperazine, thioridazine, thiothixene)

* Unknown/unsorted: Azanator
* Belarizine
* Elbanizine
* Flotrenizine
* GSK1004723
* Napactadine
* Tagorizine
* Trelnarizine
* Trenizine

H2|

| 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

H3|

| Agonists|

* α-Methylhistamine
* Cipralisant
* Histamine
* Imetit
* Immepip
* Immethridine
* L-Histidine
* Methimepip
* Proxyfan

|

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

H4|

| 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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