brompheniramine

Modify Date: 2024-01-02 15:18:54

brompheniramine Structure
brompheniramine structure
Common Name brompheniramine
CAS Number 86-22-6 Molecular Weight 319.23900
Density 1.265 g/cm3 Boiling Point 403ºC at 760 mmHg
Molecular Formula C16H19BrN2 Melting Point N/A
MSDS N/A Flash Point 197.5ºC

 Use of brompheniramine


Brompheniramine ((±)-Brompheniramine) is a potent and orally active antihistamine of the alkylamine class. Brompheniramine is a selective histamine H1 receptor antagonist with a Kd of 6.06 nM. Brompheniramine can block the hERG channels, calcium channels, and sodium channels with IC50s of 0.90 μM, 16.12 μM and 21.26 μM, respectively. Brompheniramine has anticholinergic, antidepressant and anesthetic properties and can be used for allergic rhinitis research[1][2][3][4].

 Names

Name brompheniramine
Synonym More Synonyms

 brompheniramine Biological Activity

Description Brompheniramine ((±)-Brompheniramine) is a potent and orally active antihistamine of the alkylamine class. Brompheniramine is a selective histamine H1 receptor antagonist with a Kd of 6.06 nM. Brompheniramine can block the hERG channels, calcium channels, and sodium channels with IC50s of 0.90 μM, 16.12 μM and 21.26 μM, respectively. Brompheniramine has anticholinergic, antidepressant and anesthetic properties and can be used for allergic rhinitis research[1][2][3][4].
Related Catalog
In Vitro Brompheniramine (0.1-100 μM) blocks hERG K+ channels expressed in CHO cells in a concentration-dependent manner with an IC50 of 0.90±0.14 μM, and reduced peak tail current amplitude measured at -60 mV (cells are depolarized for 2 s to +20 mV from a holding potential of -80 mV followed by a 3s repolarization back to -60 mV)[3]. Brompheniramine (1, 10 and 100 μM) significantly shortens the APD50 and depresses the plateau phase on the action potential in guinea pig papillary muscle, as well as slightly prolongs the APD90 in guinea pig papillary muscle at 10 and 100 μM[3]. Brompheniramine (0.1-100 μM) inhibit the amplitude of the Ca2+ channel currents in rat ventricular myocytes by 14.1±1.1, 31.1±5.8, 38.0±3.8 and 90.2±3.7% at 0.1, 1, 10 and 100 μM, respectively[3]. Brompheniramine blocks muscarinic cholinergic receptors in human chinese hamster ovary (CHO) cells[4].
In Vivo Brompheniramine (0.3-3 μM; SC, single dosage) induces cutaneous analgesia in rats[1]. Animal Model: Male Sprague-Dawley rats[1] Dosage: 0.3, 0.6, 1.1, 1.5 and 3.0  μM Administration: SC, single dosage Result: Provoked cutaneous analgesia in a dose-dependent manner, with an EC50 value of 0.66 μM, and induced prolonged analgesic duration.
References

[1]. Chong-Chi Chiu, et al. Subcutaneous brompheniramine for cutaneous analgesia in rats. Eur J Pharmacol. 2019 Oct 5;860:172544.

[2]. B Cusack, et al. Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65.

[3]. Shin WH, Kim KS, Kim EJ. Electrophysiological effects of brompheniramine on cardiac ion channels and action potential. Pharmacol Res. 2006 Dec;54(6):414-20.

[4]. Yasuda SU, Yasuda RP. Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51.

 Chemical & Physical Properties

Density 1.265 g/cm3
Boiling Point 403ºC at 760 mmHg
Molecular Formula C16H19BrN2
Molecular Weight 319.23900
Flash Point 197.5ºC
Exact Mass 318.07300
PSA 16.13000
LogP 3.92770
Index of Refraction 1.577
Storage condition 2-8°C

 Synthetic Route

~68%

brompheniramine Structure

brompheniramine

CAS#:86-22-6

Literature: Botteghi, Carlo; Chelucci, Giorgio; Ponte, Gino Del; Marchetti, Mauro; Paganelli, Stefano Journal of Organic Chemistry, 1994 , vol. 59, # 23 p. 7125 - 7127

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brompheniramine Structure

brompheniramine

CAS#:86-22-6

Literature: Journal of Organic Chemistry, , vol. 59, # 23 p. 7125 - 7127

~%

brompheniramine Structure

brompheniramine

CAS#:86-22-6

Literature: Journal of Organic Chemistry, , vol. 59, # 23 p. 7125 - 7127

~%

brompheniramine Structure

brompheniramine

CAS#:86-22-6

Literature: Yakugaku Zasshi, , vol. 72, p. 1529 Chem.Abstr., , p. 8080

~%

brompheniramine Structure

brompheniramine

CAS#:86-22-6

Literature: Yakugaku Zasshi, , vol. 72, p. 1529 Chem.Abstr., , p. 8080

~%

brompheniramine Structure

brompheniramine

CAS#:86-22-6

Literature: Yakugaku Zasshi, , vol. 72, p. 1529 Chem.Abstr., , p. 8080

 Synonyms

Brompheniramine
MFCD00865691
EINECS 201-657-8
(+/-)-1-(4-bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropane
(±)-brompheniramine