ChemicalBook > CAS DataBase List > Dexchlorpheniramine Maleate

Dexchlorpheniramine Maleate

Product Name
Dexchlorpheniramine Maleate
CAS No.
2438-32-6
Chemical Name
Dexchlorpheniramine Maleate
Synonyms
Polamin;Phenamin;Sensidyn;polaramin;Polaramine;d-Form maleate;poraminemaleate;polaraminemaleate;D-CHLORPHENIRAMINE MALEATE;Chlorpheniramine d-maleate
CBNumber
CB8392741
Molecular Formula
C20H23ClN2O4
Formula Weight
390.86
MOL File
2438-32-6.mol
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Dexchlorpheniramine Maleate Property

Melting point:
112-115 °C(lit.)
alpha 
D25 +44.3° (c = 1 in dimethylformamide)
storage temp. 
2-8°C
solubility 
Very soluble in water, freely soluble in ethanol (96 per cent), in methanol and in methylene chloride.
PH
pH(10g/l, 25℃) : 4.0～5.0
Merck 
13,2198
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Safety

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
36/37/39-45
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
US6504000
HS Code 
2933399090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2803
Product name
Dexchlorpheniramine Maleate
Packaging
500MG
Price
$173
Updated
2024/03/01
Sigma-Aldrich
Product number
C4915
Product name
S-(+)-Chlorpheniramine maleate salt
Packaging
1g
Price
$102
Updated
2024/03/01
Sigma-Aldrich
Product number
1179005
Product name
Dexchlorpheniramine maleate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
300mg
Price
$436
Updated
2024/03/01
Cayman Chemical
Product number
24027
Product name
Dexchlorpheniramine (maleate)
Purity
≥98%
Packaging
500mg
Price
$59
Updated
2024/03/01
Cayman Chemical
Product number
24027
Product name
Dexchlorpheniramine (maleate)
Purity
≥98%
Packaging
1g
Price
$86
Updated
2024/03/01
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Dexchlorpheniramine Maleate Chemical Properties,Usage,Production

Description

Dexchlorpheniramine Maleate is the maleate salt form of dexchlorpheniramine, an alkylamine, and first-generation histamine antagonist with anti-allergic activity. Dexchlorpheniramine maleate competitively blocks H1 receptors, thereby preventing the actions of histamine on bronchial smooth muscle, capillaries and gastrointestinal (GI) smooth muscle. This prevents histamine-induced bronchoconstriction, vasodilation, increased capillary permeability, and GI smooth muscle spasms.

Chemical Properties

Dexchlorpheniramine maleate is a white, odourless, crystalline powder which in aqueous solution has a pH of between 4 and 5. It is freely soluble in water, soluble in alcohol and in chloroform, but only slightly soluble in benzene or ether.

Originator

Polaramine,Schering,US,1958

Uses

Dexchlorpheniramine is an antihistamine used to relieve symptoms of allergy, hay fever, and the common cold. Polaramine (dexchlorpheniramine maleate) is the dextro-isomer of chlorpheniramine maleate and the S-enantiomer of Chlorpheniramine. It is an antihistamine with anticholinergic properties. S-(+)-Chlorpheniramine maleate salt has been used to study the anticholinergic effect of Achillea millefolium and Portulaca olerace on muscarinic receptors of guinea pig tracheal smooth muscle.

Definition

ChEBI: Dexchlorpheniramine maleate is an organic molecular entity.

Manufacturing Process

Twenty grams of d-phenylsuccinic acid and 28 grams of 3-(2-pyridyl)-3-pchlorophenyl-N,N-dimethylpropylamine are dissolved in 400 ml of absolute ethyl alcohol and allowed to stand at room temperature until crystallization is effected. The crystals are filtered, washed with absolute ethyl alcohol and recrystallized from 300 ml of this solvent in the same manner. The crystals are recrystallized twice from 80% ethyl alcohol using 3.5 ml per gram of compound in the manner described above and pure d-3-(2-pyridyl)-3-pchlorophenyl-N,Ndimethylpropylamine-d-phenylsuccinate is obtained, melting point 145-147°C.
This salt is shaken with 100 ml of diethyl ether and 50 ml of 20% aqueous potassium carbonate; the ether layer is separated, dried over anhydrous potassium carbonate, filtered and the ether is removed in vacuo. The d-3-(2- pyridyl)-3-p-chlorophenyl-N,N-dimethylpropylamine so obtained is a mobile oil.
4.3 grams of the above base and 1.8 grams of maleic acid are dissolved in 20 ml isopropyl acetate and kept at room temperature until crystallization is complete. The crystals are filtered, washed with ethyl acetate and recrystallized from 15 ml of this solvent in the same manner. The crystalline d-3-(2-pyridyl)-3-p-chlorophenyl-N,N-dimethylpropylamine maleate so formed is then filtered off and dried. MP 113-115°C from US Patent 3,030,371.

brand name

Mylaramine (Morton Grove); Polaramine (Schering).

Therapeutic Function

Antihistaminic

General Description

Dexchlorpheniramine(Polaramine) is the dextrorotatory enantiomer of chlorpheniramine.In vitro and in vivo studies of the enantiomers ofchlorpheniramine showed that the antihistaminic activity existspredominantly in the dextro isomer. As mentioned previously,the dextro isomer has the (S) configuration, which issuperimposable on the (S) configuration of the more activelevorotatory enantiomer of carbinoxamine.

Biochem/physiol Actions

H1 histamine receptor antagonist; active isomer.Chlorpheniramine maleate is clinically used as a topical ointment to treat skin disorders such as sunburn, urticaria, angioedema, pruritus and insect bites.

Mode of action

Dexchlorpheniramine, the d-isomer of the racemic compound chlorpheniramine, is two times more active than chlorpheniramine. Dexchlorpheniramine does not prevent the release of histamine, but rather, competes with free histamine for binding at the H1-receptor sites, and competitively antagonizes the effects of histamine on H1- receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Blockade of H1-receptors also suppresses the formation of oedema, flare, and pruritus that result from histaminic activity. Since dexchlorpheniramine binds to central and peripheral H1-receptors, sedative effects are likely to occur. H1- antagonists are structurally similar to anticholinergic agents and therefore possess the potential to exhibit anticholinergic properties of varying degrees. They also have antipruritic effects. Dexchlorpheniramine has high antihistaminic activity, moderate anticholinergic effects and minimal sedative effects. The medicine does not possess antiemetic properties.

References

[1] P. E. CHAVES. Assessment of cytotoxicity, genotoxicity, and mutagenicity of the dexchlorpheniramine reference standard and pharmaceutical formula in human peripheral blood mononuclear cells[J]. Brazilian Journal of Pharmaceutical Sciences, 2022, 18 1. DOI:10.1590/s2175-97902022e20096.
[2] GUSTAVO FACCHINI MSC. Ultraviolet A photosensitivity profile of dexchlorpheniramine maleate and promethazine-based creams: Anti-inflammatory, antihistaminic, and skin barrier protection properties[J]. Journal of Cosmetic Dermatology, 2017, 16 4: e59-e67. DOI:10.1111/jocd.12349.
[3] MASAAKI TAGAWA. Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-chlorpheniramine, a classical antihistamine.[J]. British journal of clinical pharmacology, 2001, 52 5 1: 501-509. DOI:10.1046/J.1365-2125.2001.01471.X.
[4] DONG LIANG. Identification of anthelmintic parbendazole as a therapeutic molecule for HNSCC through connectivity map-based drug repositioning[J]. Acta Pharmaceutica Sinica B, 2022, 12 5: Pages 2429-2442. DOI:10.1016/j.apsb.2021.12.005.

Dexchlorpheniramine Maleate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Dexchlorpheniramine Maleate manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
(S)-ChlorpheniraMine Maleate Salt 2438-32-6
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-08
Dideu Industries Group Limited
Product
DEXCHLORPHENIRAMINE MALEATE 2438-32-6
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-06-17
Career Henan Chemical Co
Product
DEXCHLORPHENIRAMINE MALEATE 2438-32-6
Price
US $1.00/ASSAYS
Min. Order
1ASSAYS
Purity
98%
Supply Ability
1kg,2kg,100kg
Release date
2019-07-09

2438-32-6, Dexchlorpheniramine MaleateRelated Search:

2-Phenoxyethanol Ceramides Nicotinic acid Nicotinamide Arbutin Centella asiatica extract Squalane HexanitrodiphenylaMine Dexchlorpheniramine Maleate 2-(4-Chlorobenzyl)pyridine Pheniramine maleate DEXCHLORPHENIRAMINE Ammonium hydrogen maleate Chlorphenamine maleate 3-(4-CHLORO-PHENYL)-PROPYLAMINE 3-(2-PYRIDINYL)PROPYLAMINE BROMPHENIRAMINE MALEATE IMP. B (EP) AS MALEATE: DEXCHLORPHENIRAMINE MALEATE DEXCHLORPHENIRAMINE MALEATE IMP. A (EP) AS MALEATE: (3RS)-N,N-DIMETHYL-3-PHENYL-3-(PYRIDIN-2-YL)PROPAN-1-AMINE MALEATE

  • (+)-CHLORPHENIRAMINE MALEATE SALT
  • DEXCHLOROPHENIRAMINE MALEATE
  • DEXCHLORPHENIRAMINE MALEATE
  • D-CHLORPHENIRAMINE MALEATE
  • GAMMA-[4-CHLOROPHENYL]-N,N-DIMETHYL-2-PYRIDINEPROPANAMINE MALEATE SALT
  • (+)-2-(p-chloro-alpha-(2-(dimethylamino)ethyl)benzyl)pyridinemaleate
  • (Z)-but-2-enedioic acid,(3S)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
  • (s)-(+)-chlorpheniraminemaleate
  • dextrochlorpheniraminemaleate
  • g-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanaminemaleate
  • polaramin
  • polaraminemaleate
  • poraminemaleate
  • pyridine,2-(p-chloro-alpha-(2-(dimethylamino)ethyl)benzyl)-,maleate(1:1),(+
  • γ-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine
  • d-Form maleate
  • s-(+)-chlorpheniraminemaleate
  • [gamma-(4-chlorophenyl)-pyridine-2-propyl](dimethyl)ammonium hydrogen (Z)-maleate
  • DexchlorpheniramineMaleate-Bp/Ep/Usp
  • 2-Pyridinepropanamine, .gamma.-(4-chlorophenyl)-N,N-dimethyl-, (.gamma.S)-, (2Z)-2-butenedioate (1:1)
  • (s)-γ-(4-chlorophenyl)-n,n-dimethyl-2-pyridinepropanamine maleate salt
  • s-(+)-chlorpheniramine maleate salt
  • DEXCHLORPHENIRAMINEMALEATE,USP
  • 2-Pyridinepropanamine, γ-(4-chlorophenyl)-N,N-dimethyl-, (S)-, (Z)-2-butenedioate (1:1)
  • 2-Pyridinepropanamine, γ-(4-chlorophenyl)-N,N-dimethyl-, (γS)-, (2Z)-2-butenedioate (1:1)
  • d-2-[p-Chloro-α-(2-dimethylaminoethyl)benzyl]pyridine bimaleate
  • Dexchlorpheniramine hydrogen maleate
  • Phenamin
  • Polamin
  • Polaramine
  • Pyridine, 2-[p-chloro-α-[2-(dimethylamino)ethyl]benzyl]-, maleate (1:1), (S)- (8CI)
  • Sensidyn
  • γ-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine, (+)-Chlorpheniramine maleate salt
  • Chlorpheniramine d-maleate
  • d-Chlorpheniramine·maleic acid
  • (+)-Chloropromazine Maleate
  • Dexchlorpheniramine Maleate (300 mg)
  • (γS)-γ-(4-Chlorophenyl)-N,N-diMethyl-2-pyridinepropanaMine (2Z)-2-Butenedioate
  • 2-[p-Chloro-α-[2-(diMethylaMino)ethyl]benzyl]pyridine Maleate
  • Dexchlorpheniramine maleate CRS
  • (S)-Chlorpheniramine Maleate(Dexchlorpheniramine Maleate)
  • DEXCHLORPHENIRAMINE MALEATE USP/EP/BP
  • Dexchlorpheniramine maleateQ: What is Dexchlorpheniramine maleate Q: What is the CAS Number of Dexchlorpheniramine maleate Q: What is the storage condition of Dexchlorpheniramine maleate
  • Dexchlorpheniramine Maleate (1179005)
  • [3-(11,12-Dihydro-6H-dibenzo[b,f]azocin-5-yl)-propyl]-dimethyl-amine
  • (S)-3-(4-chlorophenyl)-N,N-dimethyl-3-(pyridin-2-yl)propan-1-amine maleate
  • Histamine Receptor,Dexchlorpheniramine Maleate,Dexchlorpheniramine,inhibit,Inhibitor
  • Brompheniramine Maleate Impurity B as Maleate
  • Brompheniramine Maleate EP Impurity B as Maleate
  • 2438-32-6
  • C20H23ClN2O4
  • 39086
  • H1 histamine receptor antagonist; active isomer.
  • DIDRONEL
  • Amines
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals