Pheniramine

Modify Date: 2024-01-10 18:04:53

Pheniramine Structure
Pheniramine structure
Common Name Pheniramine
CAS Number 86-21-5 Molecular Weight 240.34300
Density 1.018 g/cm3 Boiling Point 84 °C20 mm Hg(lit.)
Molecular Formula C16H20N2 Melting Point 30-34 °C(lit.)
MSDS N/A Flash Point 179 °F
Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger

 Use of Pheniramine


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].

 Names

Name N,N-dimethyl-3-phenyl-3-pyridin-2-ylpropan-1-amine
Synonym More Synonyms

 Pheniramine Biological Activity

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
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.

 Chemical & Physical Properties

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

 Toxicological Information

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)

 Safety Information

Symbol GHS02 GHS06 GHS08
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

 Synthetic Route

 Customs

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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 Synonyms

Histapyridamine
Avil
Propheniramine
Feniramine
pheniramine
N,N-dimethyl-3-phenyl-3-pyridin-2-yl-propan-1-amine
EINECS 201-656-2
Trimeton
Prophenpyridamine
Pyriton
Tripoton
Metron
MFCD00865659
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