| Identification | More | [Name]
PYRILAMINE MALEATE | [CAS]
59-33-6 | [Synonyms]
2-[(2-DIMETHYLAMINOETHYL)(P-METHOXYBENZYL)AMINO]PYRIDINE MALEATE
MEPYRAMINE MALEATE
MEPYRAMINE MALEATE SALT
N-[4-METHOXY-PHENYL]METHYL-N',N'-DIMETHYL-N[2-PYRIDINYL]-1,2-ETHANEDIAMINE MALEATE SALT
N-(P-METHOXYBENZYL)-N',N'-DIMETHYL-N-2-PYRIDYLETHYLENEDIAMINE MALEATE
PYRANISAMINE MALEATE
PYRILAMINE MALEATE
PYRILAMINE MALEATE SALT
(z)-2-butenedioat
1,2-Ethanediamine,N-[(4-methoxyphenyl)methyl]-N’,N’-dimethyl-N-2-pyridinyl-,(Z)-2-butenedioate(1:1)
2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)pyridinebimaleate
2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)-pyridinmaleate(1:1)
2786r.p.maleate
2-ethanediamine,n-[(4-methoxyphenyl)methyl]-n’,n’-dimethyl-n-2-pyridinyl-(
anisopyradamine
anthisanmaleate
antihist
diaminidemaleate
minihist
n-((4-methoxyphenyl)methyl)-n,n’-dimethyl-n-2-pyridinyl-2-ethanediamine | [EINECS(EC#)]
200-422-7 | [Molecular Formula]
C21H27N3O5 | [MDL Number]
MFCD00069333 | [Molecular Weight]
401.46 | [MOL File]
59-33-6.mol |
| Chemical Properties | Back Directory | [Appearance]
solid | [Melting point ]
101-103°C | [storage temp. ]
2-8°C | [solubility ]
Very soluble in water, freely soluble in ethanol (96 per cent). | [form ]
neat | [color ]
White | [Stability:]
Stability Combustible. Incompatible with strong oxidizing agents. | [Water Solubility ]
Soluble in water at 100mg/ml | [Usage]
Mepyramine maleate is used as bulk pharmaceutical (antihistaminic). Product Data Sheet | [λmax]
310nm(EtOH)(lit.) | [Merck ]
14,7984 | [Major Application]
pharmaceutical (small molecule) | [InChI]
1S/C17H23N3O.C4H4O4/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15;5-3(6)1-2-4(7)8/h4-11H,12-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1- | [InChIKey]
JXYWFNAQESKDNC-BTJKTKAUSA-N | [SMILES]
OC(=O)\C=C/C(O)=O.COc1ccc(CN(CCN(C)C)c2ccccn2)cc1 | [LogP]
2.751 (est) | [CAS DataBase Reference]
59-33-6(CAS DataBase Reference) | [EPA Substance Registry System]
Pyrilamine maleate (59-33-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [RTECS ]
UT1225000
| [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
2933399090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | [Safety Profile]
A human poison by
ingestion. An experimental poison by
ingestion, subcutaneous, intravenous, and
intraperitoneal routes. Experimental
reproductive effects. Questionable
carcinogen with experimental tumorigenic
data. Mutation data reported. An
antihistamine. When heated to
decomposition it emits toxic fumes of NOx. | [Toxicity]
LD50 orally in mice: 338 mg/kg (Hunziker) |
| Hazard Information | Back Directory | [General Description]
White crystals or powder. Melting point 100-101°C. Bitter saline taste. An antihistaminic medicine. | [Reactivity Profile]
PYRILAMINE MALEATE(59-33-6) is an acidic salt of an amine. Usually does not react as either oxidizing agents or reducing agents but such behavior is not impossible. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. | [Air & Water Reactions]
Water soluble. | [Health Hazard]
SYMPTOMS: Symptoms of exposure to this compound may include drowsiness, potentiation of the sedative effect of barbituates, fatigues, vertigo, incoordination, tremor, muscle weakness, dryness of the mouth and throat, tinnitus, pupillary dilation, blurred vision, urinary retention, impotence, epigastric and intestinal pain, anorexia, nausea, vomiting, diarrhea, excitation, euphoria, insomnia, nervousness, palpitation, tachycardia, hypotension, hypersensitivity reactions, respiratory depression, coma and delirium. | [Fire Hazard]
Flash point data for this chemical are not available, however PYRILAMINE MALEATE is probably combustible. | [Description]
Mepyramine is a first generation antihistamine that acts as an inverse agonist at the histamine H1 receptor. It is reported to bind with high affinity to a Gq/11 protein-coupled form of the receptor and to promote a G protein-coupled inactive state of the H1 receptor that interferes with the Gq/11-mediated signaling of the endogenously expressed receptor, as well as to reduce G protein availability for other non-related receptors associated with this signaling pathway.1 Mepyramine has been shown to inhibit histamine-induced inositol phosphate production with a log EC50 value of -7.94.1 | [Chemical Properties]
solid | [Uses]
A histamine H1 receptor antagonist | [Uses]
Mepyramine maleate is used as bulk pharmaceutical (antihistaminic). Product Data Sheet | [Uses]
Pyrilamine maleate Selective inverse agonist for the H-1 histamine receptor. Pyrilamine Maleate is commonly utilized as a radioligand ([3H]Mepyramine) binding assay for the H1 receptor. And also used to exhibit blocking ability of KCNQ/M channels which is potentially related to an adverse effect seen in excess intake of antihistamines. | [Brand name]
Histavet-P [Veterinary] (Schering-Plough Animal Health); Pymafed (HoechstRoussel). | [Biological Activity]
Selective inverse agonist for the H 1 receptor. Inhibits histamine induced inositol phosphate (InsP) production (log EC50 = -7.94) and intracellular calcium mobilization. Sequesters G q/11 protein, reducing its availability for other receptors associated with the same signaling pathway. | [Biochem/physiol Actions]
Pyrilamine maleate is a H1 histamine receptor antagonist. Pyrilamine maleate induces sleep in vertebrates. In Cassiopea, it induces concentration dependent dormancy. | [Veterinary Drugs and Treatments]
Antihistamines are used in veterinary medicine to reduce or help
prevent histamine mediated adverse effects; predominantly used in
horses. | [storage]
4°C, protect from light | [References]
[1] CARLOS P FITZSIMONS. Mepyramine, a histamine H1 receptor inverse agonist, binds preferentially to a G protein-coupled form of the receptor and sequesters G protein.[J]. The Journal of Biological Chemistry, 2004, 279 33: 34431-34439. DOI: 10.1074/jbc.m400738200 |
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