Pheniramine

Pheniramine Basic information
Product Name:Pheniramine
Synonyms:n,n-dimethyl-3-phenyl-3-(2-pyridyl)propylamine;PHENIRAMINE;2-(alpha-(2-(dimethylamino)ethyl)benzyl)-pyridin;2-[(S)-α-[2-(Dimethylamino)ethyl]benzyl]pyridine;2-[α-(2-Dimethylaminoethyl)benzyl]pyridine;Pheniramine solution;N,N-dimethyl-3-phenyl-3-pyridin-2-ylpropan-1-amine;Dexchlorpheniramine EP Impurity A
CAS:86-21-5
MF:C16H20N2
MW:240.34
EINECS:201-656-2
Product Categories:
Mol File:86-21-5.mol
Pheniramine Structure
Pheniramine Chemical Properties
Melting point <25 °C
Boiling point bp13 181°; bp2 142°; bp0.5 135°
density 1.0081
refractive index nD25 1.5519 to 1.5521
Fp 9℃
storage temp. -20°C
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pkapKa 4.03± 0.08;9.32± 0.06(H2O,t undefined,I=0.30(NaCl)) (Uncertain)
form Oil
color Colourless
InChIKeyIJHNSHDBIRRJRN-UHFFFAOYSA-N
CAS DataBase Reference86-21-5(CAS DataBase Reference)
NIST Chemistry ReferencePyridine, 2[alpha-(2-dimethyl aminoethyl)benzyl](86-21-5)
Safety Information
Hazard Codes F,T
Risk Statements 11-23/24/25-39/23/24/25
Safety Statements 16-36/37-45
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 1
MSDS Information
Pheniramine Usage And Synthesis
OriginatorTrimeton Maleate, Schering ,US,1948
UsesPheniramine is an antigripal drug. Also, it is derived from 2-Benzylpyridine (B288740), which is a benzylpyridine with antifungal properties. 2-Benzylpyridine is also used as a chromogenic reagent for micro determination of Molybednum.
DefinitionChEBI: N,N-dimethyl-3-phenyl-3-(2-pyridinyl)-1-propanamine is a tertiary amino compound and a member of pyridines.
Manufacturing ProcessAccording 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 FunctionAntihistaminic
Synthesis Reference(s)The Journal of Organic Chemistry, 59, p. 7125, 1994 DOI: 10.1021/jo00102a044
Safety ProfilePoison by intravenous route. Human systemic effects by ingestion: central nervous system effects. When heated to decomposition it emits toxic fumes of NOx.
Enzyme inhibitorThis antihistamine (FWfree-base = 240.35 g/mol; CAS 86-21-5; insoluble in water; maleate and p-aminosalicylate salts are water-soluble), also known as N,N-dimethyl-g-phenyl-2-pyridinepropanamide, is more frequently abused than other antihistamines relative to its market share. One of the histamine H1 antagonists with little sedative action, pheniramine is often used in treatment of hay fever, rhinitis, allergic dermatoses, and pruritus. Target(s): H1 histamine receptor; and histamine Nmethyltransferase, mildly inhibited.
Pheniramine Preparation Products And Raw materials
Raw materialsPOTASSIUM AMIDE-->2-Benzylpyridine-->Maleic acid
Chlorodimethylphenylsilane N,N-Dimethylformamide ETHANE (-)-2-[METHYLAMINO]-1-PHENYLPROPANE 3-Dimethylaminopropylamine CHLORODIMETHYLVINYLSILANE PHENYL VALERATE Dimethyl fumarate 2,6-Lutidine N,N-Dimethyldodecylamine Dimethyl sulfoxide Propylamine Dimethyl ether Pyridine Dimethyl carbonate Phenylacetic acid PHENIRAMINE MALEATE,PHENIRAMINE MALEATE SALT Dimethyl sulfate

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