CAS 59-42-7|(R)-(-)-Phenylephrine
Introduction：Basic information about CAS 59-42-7|(R)-(-)-Phenylephrine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | (R)-(-)-Phenylephrine | ||
|---|---|---|---|
| CAS Number | 59-42-7 | Molecular Weight | 167.20500 |
| Density | 1.159 g/cm3 | Boiling Point | 341.1ºC at 760 mmHg |
| Molecular Formula | C9H13NO2 | Melting Point | 171°C |
| MSDS | / | Flash Point | 163.4ºC |
Names
| Name | phenylephrine |
|---|---|
| Synonym | More Synonyms |
(R)-(-)-Phenylephrine BiologicalActivity
| Description | (R)-(-)-Phenylephrine is a selective α1-adrenoceptor agonist primarily used as a decongestant. |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorResearch Areas >>Metabolic Disease |
| In Vitro | (R)-(-)-Phenylephrine is a selective α1-adrenoceptor agonist with pKi values of 5.86, 4.87 and 4.70 for α1D, α1B and α1A receptors respectively[1][2]. Phenylephrine promotes cardiac fibroblast proliferation. Phenylephrine activates CaN and evokes NFAT3 nuclear translocation. It suggests that the Ca(2+)/CaN/NFAT pathway mediates phenylephrine -induced cardiac fibroblast proliferation, and this pathway might be a possible therapeutic target in cardiac fibrosis[3]. |
| In Vivo | Perfusion of hearts with 100 μM phenylephrine causes a rapid (maximal at 10 min) 12-fold activation of two p38-MAPK isoforms. α1-adrenoceptor agonists such as phenylephrine increase the contractility of the heart. Phenylephrine also activates SAPKs/JNKs in neonatal ventricular myocytes[4]. Phenylephrine could increase the alveolar fluid clearance in high tidal volume-ventilated rats and accelerate the absorption of pulmonary edema[5]. |
| Animal Admin | Rats: A total of 170 male Wistar rats are randomLy allocated into 17 groups (n=10) using random number tables. Short-term (40 minutes) mechanical ventilation with high tidal volume is performed to induce lung injury, impair active Na+ transport and lung liquid clearance in the rats. Unventilated rats serves as controls. To demonstrate the effect of phenylephrine on alveolar fluid clearance, phenylephrine at different concentrations (10, 1, 0.1, 0.01, and 0.001 μM) is injected into the alveolar space of the HVT ventilated rats[5]. |
| References | [1]. Ford AP, et al. Pharmacological pleiotropism of the human recombinant alpha1A-adrenoceptor: implications foralpha1-adrenoceptor classification. Br J Pharmacol. 1997 Jul;121(6):1127-35. [2]. Minneman KP, et al. Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes. Mol Pharmacol. 1994 Nov;46(5):929-36. [3]. Wang J, et al. Phenylephrine promotes cardiac fibroblast proliferation through calcineurin-NFAT pathway. Front Biosci (Landmark Ed). 2016 Jan 1;21:502-13. [4]. Lazou A, et al. Activation of mitogen-activated protein kinases (p38-MAPKs, SAPKs/JNKs and ERKs) by the G-protein-coupled receptor agonist phenylephrine in the perfused rat heart. Biochem J. 1998 Jun 1;332 ( Pt 2):459-65. [5]. Li NJ, et al. Effect of phenylephrine on alveolar fluid clearance in ventilator-induced lung injury. Chin Med Sci J. 2013 Mar;28(1):1-6. |
Chemical & Physical Properties
| Density | 1.159 g/cm3 |
|---|---|
| Boiling Point | 341.1ºC at 760 mmHg |
| Melting Point | 171°C |
| Molecular Formula | C9H13NO2 |
| Molecular Weight | 167.20500 |
| Flash Point | 163.4ºC |
| Exact Mass | 167.09500 |
| PSA | 52.49000 |
| LogP | 1.03590 |
| Index of Refraction | -55.5 ° (C=5, 1mol/L HCl) |
| InChIKey | SONNWYBIRXJNDC-VIFPVBQESA-N |
| SMILES | CNCC(O)c1cccc(O)c1 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Ocular
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 188 ug/kg
- TOXIC EFFECTS :
- Vascular - BP elevation not characterized in autonomic section
- REFERENCE :
- ANESAV Anesthesiology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1940- Volume(issue)/page/year: 36,187,1972
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Ocular
- SPECIES OBSERVED :
- Human - infant
- DOSE/DURATION :
- 5500 ug/kg
- TOXIC EFFECTS :
- Vascular - BP elevation not characterized in autonomic section
- REFERENCE :
- ANESAV Anesthesiology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1940- Volume(issue)/page/year: 36,187,1972
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 350 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 180,155,1969
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 28 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 85,119,1945
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraduodenal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 65 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 180,155,1969
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 60 mg/kg
- TOXIC EFFECTS :
- Cardiac - other changes
- REFERENCE :
- JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 160,22,1968
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 875 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 28,46,1965
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 38 mg/kg
- TOXIC EFFECTS :
- Behavioral - changes in motor activity (specific assay) Cardiac - pulse rate increase, without fall in BP Skin and Appendages - hair
- REFERENCE :
- APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 38,474,1976 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- DOSE :
- 20 ug/kg
- SEX/DURATION :
- female 16 week(s) after conception
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - uterus, cervix, vagina
- REFERENCE :
- AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 143,170,1982
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- DOSE :
- 40 ug/kg
- SEX/DURATION :
- female 16 week(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow)
- REFERENCE :
- AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 143,170,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80598 No. of Facilities: 97 (estimated) No. of Industries: 2 No. of Occupations: 3 No. of Employees: 183 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80598 No. of Facilities: 147 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 6641 (estimated) No. of Female Employees: 5606 (estimated)
Safety Information
| Hazard Codes | Xn |
|---|---|
| Risk Phrases | R22 |
| Safety Phrases | S26-S36-S45 |
| RTECS | DO7175000 |
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Synonyms
| Neophryn |
| Mydfrin |
| Mesatone |
| Mesaton |
| Phenylephrine |
| Nostril |
| EINECS 200-424-8 |
| MFCD00044749 |
| Mezaton |
| Adrianol |
| Isophrin |
| Prefrin |
| (R)-(-)-Phenylephrine |
