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86-21-5

86-21-5 Structure

86-21-5 Structure
IdentificationMore
[Name]

Pheniramine
[CAS]

86-21-5
[Synonyms]

1-phenyl-1-(2-pyridyl)-3-dimethylaminopropane
2-(3-dimethylamino-1-phenylpropyl)pyridine
n,n-dimethyl-3-phenyl-3-(2-pyridyl)propylamine
PHENIRAMINE
2-(alpha-(2-(dimethylamino)ethyl)benzyl)-pyridin
2-(alpha-(2-dimethylaminoethyl)benzyl)pyridine
2-[alpha-[2-(Dimethylamino)ethyl]benzyl]pyridine
2-Pyridinepropanamine, N,N-dimethyl-gamma-phenyl-
3-Phenyl-3-(2-pyridyl)-N,N-dimethylpropylamine
3-phenyl-3-(2-pyridyl)-n,n-dimethylpropylanine
AVIL
Feniramine
Metron
N,N-Dimethyl-3-phenyl-3-(2-pyridinyl)-1-propanamine
n,n-dimethyl-gamma-phenyl-2-pyridinepropanamin
NCI-C60695
Propheniramine
Prophenpyridamine
Pyridine, 2-[alpha-[2-(dimethylamino)ethyl]benzyl]-
Pyriton
[EINECS(EC#)]

201-656-2
[Molecular Formula]

C16H20N2
[MDL Number]

MFCD00865659
[Molecular Weight]

240.34
[MOL File]

86-21-5.mol
Chemical PropertiesBack Directory
[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)
[form ]

Oil
[pka]

pKa 4.03± 0.08;9.32± 0.06(H2O,t undefined,I=0.30(NaCl)) (Uncertain)
[color ]

Colourless
[InChIKey]

IJHNSHDBIRRJRN-UHFFFAOYSA-N
[CAS DataBase Reference]

86-21-5(CAS DataBase Reference)
[NIST Chemistry Reference]

Pyridine, 2[alpha-(2-dimethyl aminoethyl)benzyl](86-21-5)
Safety DataBack Directory
[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
[Safety Profile]

Poison by intravenous route. Human systemic effects by ingestion: central nervous system effects. When heated to decomposition it emits toxic fumes of NOx.
Hazard InformationBack Directory
[Originator]

Trimeton Maleate, Schering ,US,1948
[Uses]

Pheniramine 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.
[Definition]

ChEBI: N,N-dimethyl-3-phenyl-3-(2-pyridinyl)-1-propanamine is a tertiary amino compound and a member of pyridines.
[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
[Synthesis Reference(s)]

The Journal of Organic Chemistry, 59, p. 7125, 1994 DOI: 10.1021/jo00102a044
[Enzyme inhibitor]

This 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.
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