59-33-6

Basic information

• Product Name: PYRILAMINE MALEATE
• Synonyms: MEPYRAMINE MALEATE;MEPYRAMINE MALEATE SALT;2-[(2-DIMETHYLAMINOETHYL)(P-METHOXYBENZYL)AMINO]PYRIDINE MALEATE;PYRILAMINE MALEATE;PYRILAMINE MALEATE SALT;PYRANISAMINE MALEATE;N-(P-METHOXYBENZYL)-N',N'-DIMETHYL-N-2-PYRIDYLETHYLENEDIAMINE MALEATE;N-[4-METHOXY-PHENYL]METHYL-N',N'-DIMETHYL-N[2-PYRIDINYL]-1,2-ETHANEDIAMINE MALEATE SALT
• CAS NO: 59-33-6
• Molecular Formula: C₄H₃O₄*C₁₇H₂₄N₃O
• Molecular Weight: 401.46
• EINECS: 200-422-7
• Product Categories: Histamine receptor;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;ANTAMINE
• Mol File: 59-33-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 101-103°C
• Boiling Point: 423.8 °C at 760 mmHg
• Flash Point: 210.1 °C
• Appearance: solid
• Storage Temp.: 2-8°C
• Solubility: Very soluble in water, freely soluble in ethanol (96 per cent).
• Water Solubility: Soluble in water at 100mg/ml
• Stability: Stability Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,7984
• CAS DataBase Reference: PYRILAMINE MALEATE(CAS DataBase Reference)
• NIST Chemistry Reference: PYRILAMINE MALEATE(59-33-6)
• EPA Substance Registry System: PYRILAMINE MALEATE(59-33-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: UT1225000
• TSCA: Yes
• Hazardous Substances Data: 59-33-6(Hazardous Substances Data)

Usage

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. Mepyramine has been shown to inhibit histamine-induced inositol phosphate production with a log EC50 value of -7.94.

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 59-33-6 differently. You can refer to the following data:
1. Mepyramine maleate is used as bulk pharmaceutical (antihistaminic). Product Data Sheet
2. 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.
3. A histamine H1 receptor antagonist

Brand name

Histavet-P [Veterinary] (Schering-Plough Animal Health); Pymafed (HoechstRoussel).

General Description

Different sources of media describe the General Description of 59-33-6 differently. You can refer to the following data:
1. Pyrilamine, 2-[4-methoxybenzyl[2-dimethylamino)ethyl]-amino]pyridine, is available as theacid maleate salt (1:1), which is a white crystalline powderwith a faint odor and a bitter, saline taste. The salt is solublein water (1:0.4) and freely soluble in alcohol. A 10% solutionhas a pH of approximately 5. At a pH of 7.5 or above,the free base begins to precipitate.Pyrilamine differs structurally from tripelennamine byhaving a methoxy group in the para position of the benzylradical. It differs from its more toxic and less potent precursorphenbenzamine (Antergan) by having a 2-pyridyl groupon the nitrogen atom in place of a phenyl group.Clinically, pyrilamine and tripelennamine are consideredamong the less potent antihistaminics. They are highly potent,however, in antagonizing histamine-induced contractionsof guinea pig ileum. Because of the pronounced localanesthetic action, the drug should not be chewed, but takenwith food.
2. White crystals or powder. Melting point 100-101°C. Bitter saline taste. An antihistaminic medicine.

Air & Water Reactions

Water soluble.

Reactivity Profile

PYRILAMINE MALEATE 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.

Health Hazard

SYMPTOMS: Symptoms of exposure to PYRILAMINE MALEATE 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 PYRILAMINE MALEATE are not available, however PYRILAMINE MALEATE is probably combustible.

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.

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.

Veterinary Drugs and Treatments

Antihistamines are used in veterinary medicine to reduce or help prevent histamine mediated adverse effects; predominantly used in horses.

InChI:InChI=1/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)/p-2/b;2-1-

Synthetic route

mepyramine maleate (59-33-6) → N-(4-hydroxybenzyl)-N',N'-dimethyl-N-2-pyridinyl-1,2-ethanediamine maleate

Conditions	Yield
With sodium methylate In methanol; dimethyl sulfoxide for 96h; Heating;	57%

potassium pentacyanonitrosylchromate(III) monohydrate + mepyramine maleate (59-33-6) → {Cr(NO)(CN)2(mepyramine maleate)2(H2O)}

Conditions	Yield
With CH3COOH In acetic acid byproducts: CH3COOK, H2O, HCN; aq. acetic acid; 20-30 min, 80°C; CO2 bubbled (few h) to remove HCN; ppt. washed (H2O repeatedly; ethanol); dried (vac., over silica gel, room temp., to const. wt.); elem.anal.;	53%

mepyramine maleate (59-33-6) → iodomepyramine (109912-26-7)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid; sodium iodide In acetic acid at 22℃; for 1.5h;	47%

pentaisothiocyanatonitrosylchromate(I) + mepyramine maleate (59-33-6) → Cr(NO)(NCS)2(C17H23N3O)2(H2O)*2C4H4O4

Conditions	Yield
In acetic acid aq. acetic acid; shaking, reflux (80°C, 1-2 h), ice cooling, pptn.; filtration, washing (CH3COOH(aq.), water), drying (vac., room temp.); elem. anal.;	40%

mepyramine maleate (59-33-6) → N-(4-hydroxy-3,5-di-iodobenzyl)-N',N'-dimethyl-N-2-pyridinyl-1,2-ethanediamine (109912-27-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 57 percent / sodium methoxide / methanol; dimethylsulfoxide / 96 h / Heating 2: iodine, potassium iodide, 30percent aq. methylamine / H2O / 1.) 10 deg C, 3 h, 2.) 23 deg C, 10 h View Scheme

Downstream Products

• 109912-27-8 N-(4-hydroxy-3,5-di-iodobenzyl)-N',N'-dimethyl-N-2-pyridinyl-1,2-ethanediamine 
• 109912-26-7 iodomepyramine 

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