132-20-7

Basic information

• Product Name: Pheniramine maleate
• Synonyms: PROPHENPYRIDAMINE MALEATE;PHENIRAMINE MALEATE;PHENIRAMINE MALEATE SALT;PHENIRAMIN MALEATE;1-(n,n-dimethylamino)-3-(phenyl-3-alpha-pyridyl)propanemaleate;2-(alpha-(2-(dimethylamino)ethyl)benzyl)pyridine,bimaleate;2-(alpha-(2-(dimethylamino)ethyl)benzyl)pyridine,maleate;2-(alpha-(2-(dimethylamino)ethyl)benzyl)-pyridinmaleate(1:1)
• CAS NO: 132-20-7
• Molecular Formula: C₄H₃O₄*C₁₆H₂₁N₂
• Molecular Weight: 356.42
• EINECS: 205-051-4
• Product Categories: Antagonists;Histaminergics;Neurotransmitters;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 132-20-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 104-108°C
• Boiling Point: 489.25°C (rough estimate)
• Flash Point: 164.5 °C
• Appearance: white powder
• Density: 1.2233 (rough estimate)
• Vapor Pressure: 5.07E-05mmHg at 25°C
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Very soluble in water, freely soluble in ethanol (96 per cent), in methanol and in methylene chloride.
• Water Solubility: >=1 g/100 mL at 24 ºC
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,7235
• CAS DataBase Reference: Pheniramine maleate(CAS DataBase Reference)
• NIST Chemistry Reference: Pheniramine maleate(132-20-7)
• EPA Substance Registry System: Pheniramine maleate(132-20-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: UT0175000
• Hazardous Substances Data: 132-20-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Originator

Trimeton Maleate, Schering ,US,1948

Uses

Different sources of media describe the Uses of 132-20-7 differently. You can refer to the following data:
1. Pheniramine, a H1-receptor antagonist, is an antihistamine with anticholinergic and sedative properties. Pheniramine is used to treat allergic conditions such as hay fever or urticaria.
2. Antihistaminic;H1 antagonist
3. A H1 histamine receptor antagonist.
4. Used medicinally as an antihistaminic (merck).

Manufacturing Process

According to US Patent 2,676,964: to 1.0 mol of potassium amide in 3 liters of liquid ammonia, is added 1.0 mol of 2-benzylpyridine. After 15 minutes, 1.1 mols of β-dimethylaminoethyl chloride are added. The ammonia is allowed to evaporate and the reaction product decomposed with water and ether extracted. The ether layer is dried over sodium sulfate and after evaporation the residue is distilled, giving the 3-phenyl-3-(2-pyridyl)-N,Ndimethylpropylamine, BP 139°-142°C/1-2 mm. The maleate is produced by reaction with maleic acid.

Therapeutic Function

Antihistaminic

General Description

Different sources of media describe the General Description of 132-20-7 differently. You can refer to the following data:
1. Pheniramine maleate, 2-[α-[2-dimethylaminoethyl]benzyl]-pyridine bimaleate (Trimeton,Inhiston), is a white crystalline powder, with a faint aminelikeodor, which is soluble in water (1:5) and very soluble inalcohol. This drug is the least potent member of the seriesand is marketed as the racemate. The usual adult dose is 20to 40 mg 3 times daily. It is available in certain combinationproducts.
2. White powder with a faint amine-like odor. Melting point 107°C. pH (1% solution) 4.5-5.5. Used medicinally as an antihistaminic.

Air & Water Reactions

Water soluble.

Reactivity Profile

Pheniramine maleate gives weakly acidic aqueous solutions. May react with strong oxidizing agents.

Fire Hazard

Flash point data are not available for Pheniramine maleate, but Pheniramine maleate is probably combustible.

Biochem/physiol Actions

Pheniramine maleate is a H1 histamine receptor antagonist. It is an alkylamine derivative. Structurally, pheniramine contains a chiral carbon atom with a hydrogen atom. Other substituents include the pyridyl, alkylamine and phenyl groups. It is used as an antiallergic drug for treating the common cold, respiratory allergies, urticaria, and systematic allergic reactions.

InChI:InChI=1/C16H20N2.C3H4O4/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16;4-2(5)1-3(6)7/h3-10,12,15H,11,13H2,1-2H3;1H2,(H,4,5)(H,6,7)

Synthetic route

pheniramine (86-21-5) + maleic acid (110-16-7) → pheniramine maleate (132-20-7)

Conditions	Yield
In ethanol at 20℃; Solvent;	5.1 g

benzyl boronic acid (4463-42-7) → pheniramine maleate (132-20-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / N,N-dimethyl-formamide; tetrahydrofuran; water / 3 h / 75 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C 3: ethanol / 20 °C View Scheme

2-bromo-pyridine (109-04-6) → pheniramine maleate (132-20-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / N,N-dimethyl-formamide; tetrahydrofuran; water / 3 h / 75 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C 3: ethanol / 20 °C View Scheme

potassium pentacyanonitrosylchromate(III) monohydrate + pheniramine maleate (132-20-7) → {Cr(NO)(CN)2(pheniramine 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.;	59%

tetracyanodinitrosylmolybdate(0) + pheniramine maleate (132-20-7) → Mo(NO)2(CN)2(C5H4NCH(CH2CH2N(CH3)2)C6H5)2*2(HCCOOH)2*2H2O=(Mo(NO)2(CN)2(C16H20N2)2)*((HCCOOH)2)2*2H2O

Conditions	Yield
In water; acetic acid addn. of ligand in a mixt. of water/acetic acid to a filtered aq. soln. of molybdate with shaking, refluxing for 4-5 h over a hot plate at 80°C; filtn. by suction, washing several times with dilute acetic acid, finally with water, drying in vacuo at room temp. to a constant weight, elem. anal.;	53%

pentaisothiocyanatonitrosylchromate(I) + pheniramine maleate (132-20-7) → Cr(NO)(NCS)2(C16H20N2)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.;	45%

tetracyanonitrosylchromate(I) anion + water (7732-18-5) + pheniramine maleate (132-20-7) → [Cr(NO)(CN)2(C5H4N(C6H5)CHCH2CH2N(CH3)2)(H2O)]*HOOCCHCHCOOH

Conditions	Yield
In water; acetic acid adding aq.-AcOH soln. of ligand to aq. soln. of Cr complex with shaking,refluxing for 30-45 min at 80°C; filtering ppt. by suction, washing with dild. AcOH and water, drying in vacuo; elem. anal.;	42%

Upstream product

• 86-21-5 pheniramine 
• 110-16-7 maleic acid 
• 4463-42-7 benzyl boronic acid 
• 109-04-6 2-bromo-pyridine 

Related news

Development and validation of a UV-spectrophotometric method for the determination of Pheniramine maleate (cas 132-20-7) and its stability studies09/30/2019

A sensitive, precise, and cost-effective UV-spectrophotometric method is described for the determination of pheniramine maleate (PAM) in bulk drug and tablets. The method is based on the measurement of absorbance of a PAM solution in 0.1 N HCl at 264 nm. As per the International Conference on Ha...detailed

Sensitive and selective spectrophotometric methods for the determination of Pheniramine maleate (cas 132-20-7) in bulk drug and in its formulations using sodium hypochlorite09/29/2019

Two simple, selective and sensitive spectrophotometric methods are described for the determination of pheniramine maleate (PAM) in pure and dosage forms. The method is based on the reaction of PAM with hypochlorite in the presence of Kolthoff buffer (phosphate-borate) of pH 7.0 to form the chlor...detailed

Assessment of Protective Effects of Methylprednisolone and Pheniramine maleate (cas 132-20-7) on Reperfusion Injury in Kidney After Distant Organ Ischemia: A Rat Model10/01/2019

Ischemia/reperfusion (I/R) injury of tissues is a common problem that cardiovascular surgeons are faced with. Suppression of inflammation, which plays an important role in the pathogenesis of I/R injury, may reduce this damage. The aim of this study is to investigate the protective effects of me...detailed

Relevant articles and documents

A synthetic method of pheniramine maleate

A novel synthetic method of pheniramine maleate is provided. The method includes subjecting benzylboronic acid and 2-halogenpyridine to a condensation reaction to obtain 2-benzylpyridine, subjecting the 2-benzylpyridine and 2-dimethylaminoethyl halide hydrochloride to a substitution reaction to prepare pheniramine, and salifying the pheniramine with maleic acid to obtain the pheniramine maleate. The method is simple in process, high in yield, low in cost and easy in industrial production.