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T4951

Sigma-Aldrich

2-((3-Trifluoromethyl)phenyl)histamine dimaleate

≥98% (HPLC), powder

Synonyme(s) :

(2-[2-(3-Trifluoromethyl)phenyl)-1H-imidazol-4-yl]ethanamine dimaleate, Compound 39

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About This Item

Formule empirique (notation de Hill):
C20H20F3N3O8
Numéro CAS:
162049-83-4
Poids moléculaire :
487.38
Numéro MDL:
MFCD08277024
Code UNSPSC :
12352116
ID de substance PubChem :
329826803
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

off-white

Solubilité

H2O: ~20 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.NCCc1c[nH]c(n1)-c2cccc(c2)C(F)(F)F

InChI

1S/C12H12F3N3.2C4H4O4/c13-12(14,15)9-3-1-2-8(6-9)11-17-7-10(18-11)4-5-16;2*5-3(6)1-2-4(7)8/h1-3,6-7H,4-5,16H2,(H,17,18);2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

Clé InChI

GGDUVPKRZGATLR-SPIKMXEPSA-N

Application

2-((3-Trifluoromethyl)phenyl)histamine dimaleate has been used to study the induction of goblet cell secretion in rats3. 2-((3-Trifluoromethyl)phenyl)histamine dimaleate has also been used to study the role of H1 receptor in COX-2 regulation and prostanoid homeostasis in human vascular endothelial cells4.

Actions biochimiques/physiologiques

2-((3-Trifluoromethyl)phenyl)histamine dimaleate was found to be the most potent and selective H1 histamine receptor agonist of a panel of compounds in functional in vitro studies on histamine H2, H3, and other neurotransmitter receptors. It showed better potency at the guinea pig H1 histamine receptor than at the human H1 histamine receptor (pKi : 5.9). The selectivity of 2-((3-Trifluoromethyl)phenyl)histamine dimaleate was found to be 2138 (H1:H2), > 64 (H1:H3), 1000 (H1:M3), 105 (H1: a1), 708 (H1:β1), and 71 (H1:5HT2A). 2-((3-Trifluoromethyl)phenyl)histamine dimaleate does not cross the blood-brain barrier.

Caractéristiques et avantages

This compound is featured on the Histamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Notes préparatoires

2-((3-Trifluoromethyl)phenyl)histamine dimaleate is soluble in water at approximately 20 mg/ml.

Pictogrammes

Skull and crossbonesCorrosion
GHS06,GHS05

Mention d'avertissement

Danger

Mentions de danger

H301,H315,H318,H335

Classification des risques

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

C Leschke et al.
Journal of medicinal chemistry, 38(8), 1287-1294 (1995-04-14)
New histamine derivatives characterized by a (substituted) aryl, heteroaryl, benzyl, or heteroarylmethyl substituent in the C2 position of the imidazole ring have been prepared from appropriate imidates or amidines, respectively, and 2-oxo-4-phthalimido-1-butyl acetate (1). The compounds were screened as potential
Roland Seifert et al.
The Journal of pharmacology and experimental therapeutics, 305(3), 1104-1115 (2003-03-11)
Species isoforms of histamine H2-, H3-, and H4-receptors differ in their pharmacological properties. The study aim was to dissect differences between the human H1R (hH1R) and guinea pig H1R (ghH1R). We coexpressed hH1R and gpH1R with regulators of G-protein signaling
Densen Hayashi et al.
Investigative ophthalmology & visual science, 53(6), 2993-3003 (2012-04-03)
The purpose of this study was to determine the effect of histamine and its receptors on goblet cell secretion. Cultured rat and human goblet cells were grown in RPMI 1640. Goblet cell secretion of high molecular weight glycoconjugate was measured
Xiaoyu Tan et al.
Journal of immunology (Baltimore, Md. : 1950), 179(11), 7899-7906 (2007-11-21)
Although histamine plays an essential role in inflammation, its influence on cyclooxygenases (COX) and prostanoid homeostasis is not well understood. In this study, we investigated the effects of histamine on the expression of COX-1 and COX-2 and determined their contribution
Trinidad Raices et al.
Journal of molecular endocrinology, 63(3), 187-197 (2019-08-16)
Testicular Leydig cells (LC) are modulated by several pathways, one of them being the histaminergic system. Heme oxygenase-1 (HO-1), whose upregulation comprises the primary response to oxidative noxae, has a central homeostatic role and might dysregulate LC functions when induced.

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