CAS 86-21-5|Pheniramine
Introduction：Basic information about CAS 86-21-5|Pheniramine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | / | Flash Point | 179 °F |
| Symbol | GHS02, GHS06, GHS08 | Signal Word | Danger |
Names
| Name | N,N-dimethyl-3-phenyl-3-pyridin-2-ylpropan-1-amine |
|---|---|
| Synonym | More Synonyms |
Pheniramine BiologicalActivity
| 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 >>ApoptosisResearch Areas >>CancerSignaling Pathways >>Immunology/Inflammation >>Histamine ReceptorResearch Areas >>Inflammation/ImmunologySignaling 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. |
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 |
| InChIKey | IJHNSHDBIRRJRN-UHFFFAOYSA-N |
| SMILES | CN(C)CCC(c1ccccc1)c1ccccn1 |
| Storage condition | ?20°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
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 |
|---|---|
| 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 |
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 |
