59-42-7

59-42-7 structure

Name: (R)-(-)-Phenylephrine
Chemical Name: phenylephrine
CAS Number: 59-42-7
Molecular Formula: C₉H₁₃NO₂
Molecular Weight: 167.20500
Catalog: analytical chemistry Standard Pharmacopoeia Standards and Magazine Standards
Create Date: 2018-09-30 20:02:25
Modify Date: 2026-06-30 18:33:23
(R)-(-)-Phenylephrine is a selective α1-adrenoceptor agonist primarily used as a decongestant.

Name	phenylephrine
Synonyms	(-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol (r)-phenylhrine (r)-benzenemethano component of Cerose dm Metasynhrine m-Synhrine component of Pv tussin syrup component of Dristan nasal mist component of Hycomine compound l-alpha-Hydroxy-beta-methylamino-3-hydroxy-l-ethylbenzene Mesaton Phenylephrine Visadron MFCD00044749 PHENYLHRINE BASE Ak-dilate component of Histalet forte Adrianol m-Sympatol Neophryn Mesatone Alcon efrin R(-)-Phenylhrine component of Ru-tuss liquid component of Vasosulf m-Oxedrine component of Entex Neosynhrine l-1-(m-Hydroxyphenyl)-2-methylaminoethanol Isophrin (-)-m-oxedrine (-)-m-hydroxy-alpha-(methylaminomethyl)benzylalcohol component of Dristan cold component of Prefrin-a l-m-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol Nostril Metasympatol Prefrin l-(3-Hydroxyphenyl)-N-methylethanolamine component of Comhist m-Sympathol l-m-hydroxy-alpha-((methylamino)methyl)benzylalcohol component of Cyclomydril component of Zincfrin component of Ru-tuss tablets component of Relief Ak-nefrin Mydfrin Metaoxedrin Pyracort D (R)-3-Hydroxy-alpha-[(methylamino)methyl]benzenemethanol hydrochloride Metaoxedrine m-Methylaminoethanolphenol EINECS 200-424-8 Mezaton Biomydrin R(-)-Mezaton Benzyl alcohol, m-hydroxy-alpha-((methylamino)methyl)-, (-) component of Decongestant (-)-PHENYLHRINE component of Demazin

Description	(R)-(-)-Phenylephrine is a selective α1-adrenoceptor agonist primarily used as a decongestant.
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Research 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.

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)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DO7175000

CHEMICAL NAME :: Benzyl alcohol, m-hydroxy-alpha-((methylamino)methyl)-, (-)-

CAS REGISTRY NUMBER :: 59-42-7

LAST UPDATED :: 199706

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C9-H13-N-O2

MOLECULAR WEIGHT :: 167.23

WISWESSER LINE NOTATION :: QR CYQ1M1 -L

HEALTH HAZARD DATA

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)

Hazard Codes	Xn
Risk Phrases	R22
Safety Phrases	S26-S36-S45
RTECS	DO7175000

94240-17-2

614-03-9

59-42-7

Literature: WO2008/77560 A1, ; Page/Page column 10-11 ;

1280541-42-5

~89%

59-42-7

Literature: Divi's Laboratories Limited Patent: US2012/108848 A1, 2012 ; Location in patent: Page/Page column 4 ;

614-03-9

~10%

59-42-7

Literature: Lin, Wei-De; Chen, Chien-Yu; Chen, Huei-Chung; Hsu, Wen-Hwei Process Biochemistry, 2010 , vol. 45, # 9 p. 1529 - 1536

94240-17-2

59-42-7

Literature: Tetrahedron Asymmetry, , vol. 21, # 20 p. 2479 - 2486

747358-03-8

59-42-7

Literature: Applied Catalysis A: General, , vol. 439-440, p. 74 - 79

591-31-1

59-42-7

Literature: Applied Catalysis A: General, , vol. 439-440, p. 74 - 79

1477-63-0

59-42-7

Literature: Monatshefte fuer Chemie, , vol. 80, p. 517,521,524,534

Precursor 5
94240-17-2 614-03-9 747358-03-8 591-31-1
1477-63-0
DownStream 2
110193-49-2 61-76-7

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