Pheniramine

[Description]:

Pheniramine (Prophenpyridamine;Tripoton) is a first-generation histamine H1 receptor antagonist, acts on the central nervous system (CNS) with sedative and hypnotic effect. Pheniramine displays antitumor effect and induces leukemia cells apoptosis. Pheniramine is also a safe and effective local anesthetic, with antipruritic effects[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor

Research Areas >> Inflammation/Immunology

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

[Target]

H1 Receptor:1.01 mM (IC50)

[In Vitro]

Pheniramine inhibits CYP2D6, the specific P450-isozymes, to delay metabolic time and prolong antihistaminic effects[1]. Pheniramine inhibits Ca2+ influx into BC3H-1 cells by inhibiting histamine with an IC50 value of 1.01 mM and regulates cellular Ca2+ transmembrane action[2]. Pheniramine (0.5, 1.0 mM; 24 h) induces cell apoptosis in human T-cell acute lymphoblastic leukemia cell lines[3]. Pheniramine (1 μM-1 mM; 12-48 h) inhibits cell proliferation in a time-dependent manner and shows inhibitory concentration IC50s of 550 μM (CCRF-CEM cells) and 420 μM (Jurkat cells), respectively[3]. Apoptosis Analysis[3] Cell Line: Human T-cell acute lymphoblastic leukemia cell lines: CCRF-CEM and Jurkat ALL Concentration: 0.5, 1.0 mM Incubation Time: 24 hours Result: Induced cells apoptosis with chromatin condenses and marginalizes, and nuclear debris spreaded into the cytoplasm. Cell Viability Assay[3] Cell Line: Human T-cell acute lymphoblastic leukemia cell lines: CCRF-CEM and Jurkat ALL Concentration: 1 μM-1 mM Incubation Time: 12, 24, 48 hours Result: Inhibited cell proliferation and survival in a time- and dose-dependent manner.

[In Vivo]

Pheniramine (1.75 μM; i.t.) exerts local anesthesia effect and results spinal block in rats[4]. Animal Model: Sprague–Dawley rats (300-350 g; male)[4] Dosage: 0.30, 0.60, 0.90, 1.50, 1.75 μM Administration: Intrathecal injection; one time Result: Resulted the spinal block and displayed dose-dependent effect. Showed 100% blockades in motor function, proprioception, and nociception, with full recoveryduration of action about 41, 56, and 88 min, respectively, at 1.75 μM.

[References]

[1]. Sharma A, et al. Classic histamine H1 receptor antagonists: a critical review of their metabolic and pharmacokinetic fate from a bird's eye view. Curr Drug Metab. 2003 Apr;4(2):105-29.

[2]. Brown RD, et al. Alpha 1-adrenergic and H1-histamine receptor control of intracellular Ca2+ in a muscle cell line: the influence of prior agonist exposure on receptor responsiveness. Mol Pharmacol. 1986 Jun;29(6):531-9.

[3]. Jangi SM, et al. Apoptosis of human T-cell acute lymphoblastic leukemia cells by diphenhydramine, an H1 histamine receptor antagonist. Oncol Res. 2004;14(7-8):363-72.

[4]. Hung CH, et al. Spinal anesthesia with diphenhydramine and pheniramine in rats. Eur J Pharmacol. 2011 Dec 30;673(1-3):20-4.

[ Density]:
1.018 g/cm3

[ Boiling Point ]:
84 °C20 mm Hg(lit.)

[ Melting Point ]:
30-34 °C(lit.)

[ Molecular Formula ]:
C₁₆H₂₀N₂

[ Molecular Weight ]:
240.34300

[ Flash Point ]:
179 °F

[ Exact Mass ]:
240.16300

[ PSA ]:
16.13000

[ LogP ]:
3.16520

[ Index of Refraction ]:
1.556

[ Storage condition ]:
?20°C

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CHEMICAL IDENTIFICATION

RTECS NUMBER :: US9625000

CHEMICAL NAME :: Pyridine, 2-(alpha-(2-(dimethylamino)ethyl)benzyl)-

CAS REGISTRY NUMBER :: 86-21-5

BEILSTEIN REFERENCE NO. :: 0192445

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C16-H20-N2

MOLECULAR WEIGHT :: 240.38

WISWESSER LINE NOTATION :: T6NJ BYR&2N1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 14 mg/kg

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - muscle contraction or spasticity

REFERENCE :: MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 2,110,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 48 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 211,328,1950

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes Endocrine - hyperglycemia Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 211,328,1950 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81485 No. of Facilities: 805 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 805 (estimated)

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
1759

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
8

[ HS Code ]:
2933399090

Click to get detail synthetic route

Precursor

DownStream

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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