59-33-6

Usage

Uses

Used in Pharmaceutical Industry:
Pyrilamine Maleate is used as a bulk pharmaceutical (antihistaminic) for treating various allergic conditions, such as rhinitis, urticaria, and pruritus. It works by blocking the H1 histamine receptor, which helps alleviate symptoms caused by histamine release during an allergic response.
Used in Research and Development:
Pyrilamine Maleate is commonly utilized as a radioligand ([3H]Mepyramine) in binding assays for the H1 receptor. This allows researchers to study the interactions between the receptor and various compounds, which can be useful in the development of new antihistamines or other related drugs.
Used in Veterinary Medicine:
Under the brand name Histavet-P, Pyrilamine Maleate is used in veterinary medicine for treating allergic conditions in animals, such as atopic dermatitis and pruritus.
Used in Drug Delivery Systems:
Pyrilamine Maleate is also used to exhibit the blocking ability of KCNQ/M channels, which is potentially related to an adverse effect seen in excess intake of antihistamines. This information can be valuable in the development of safer and more effective drug delivery systems for antihistamines.

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

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

Related news

GlC Analysis of Menthol, Phenol, Benzocaine, and PYRILAMINE MALEATE (cas 59-33-6) in Aerosol Spray Lotion07/13/2019

A GLC method is presented for the quantitative determination of menthol, phenol, benzocaine, and pyrilamine maleate. The propellent was exhausted from a pressurized can, and an aliquot of the alcoholic base was weighed. After the addition of the internal standard diluted with chloroform, 1 μl o...detailed

Comparison of the metabolism and elimination of PYRILAMINE MALEATE (cas 59-33-6) in the rat, mouse and female rhesus monkey07/12/2019

Elimination and metabolic profiles of the O-glucuronide conjugated products of pyrilamine and their nonconjugated O-dealkylated and N-desmethyl pyrilamine products were determined after the oral administration of (14C)-pyrilamine maleate to Fischer 344 rats, B6C3F1 mice and female rhesus monkeys...detailed