Shanghai Nianxing Industrial Co., Ltd
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Product Name: orciprenaline
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Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Orciprenaline
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Purity: 98.0%
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586-06-1

586-06-1 structure

586-06-1 structure

Name: orciprenaline
Chemical Name: Orciprenaline
CAS Number: 586-06-1
Molecular Formula: C₁₁H₁₇NO₃
Molecular Weight: 211.258
Catalog: API Respiratory medication Asthma
Create Date: 2018-02-20 08:00:00
Modify Date: 2024-01-05 22:08:29
Metaproterenol (Orciprenaline) is a direct-acting sympathomimetic and a β2-adrenergic receptor (β2AR) agonist with an IC50 of 68 nM. Metaproterenol also has anti-inflammatory activity[1][2].

Name	Orciprenaline
Synonyms	1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane 5-[1-hydroxy-2-(isopropanylamino)ethyl]benzene-1,3-diol Benzyl alcohol, 3,5-dihydroxy-α-((isopropylamino)methyl)- orciprenaline 1,3-Benzenediol, 5-(1-hydroxy-2-((1-methylethyl)amino)ethyl)- 5-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,3-benzenediol 1-(3,5-Dihydroxyphenyl)-2-isopropylaminoethanol Metaproterenol 3,5-Dihydroxy-a-[(isopropylamino)methyl]benzyl Alcohol 5-[1-Hydroxy-2-(isopropylamino)ethyl]-1,3-benzenediol 5-[1-Hydroxy-2-(isopropylamino)ethyl]benzene-1,3-diol EINECS 209-569-1 1,3-Benzenediol, 5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-

Description	Metaproterenol (Orciprenaline) is a direct-acting sympathomimetic and a β2-adrenergic receptor (β2AR) agonist with an IC50 of 68 nM. Metaproterenol also has anti-inflammatory activity[1][2].
Related Catalog	Research Areas >> Endocrinology
Target	IC50: 68 nM (β2-adrenergic receptor)[1]
In Vitro	Metaproterenol (10 μM; 74 hours; THP-1 cells and bone marrow macrophages) treatment enhances β-arrestin2 and its interaction with IκBα in high glucose-induced THP-1 cells and bone marrow macrophages[1]. Metaproterenol (10 μM; 74 hours; THP-1 cells and bone marrow macrophages) treatment leads to downregulation of NF-κB in high glucose-induced THP-1 cells and bone marrow macrophages[1]. Western Blot Analysis[1] Cell Line: THP-1 cells and bone marrow macrophages Concentration: 10 μM Incubation Time: 74 hours Result: Enhanced β-arrestin2 and its interaction with IκBα. RT-PCR[1] Cell Line: THP-1 cells and bone marrow macrophages Concentration: 10 μM Incubation Time: 74 hours Result: Led to downregulation of NF-κB.
In Vivo	Treatment of Zucker diabetic fatty rats with Metaproterenol for 12 weeks attenuates monocyte activation as well as pro-inflammatory and pro-fibrotic responses in the kidneys and heart. Thus, Metaproterenol might has protective effects against diabetic renal and cardiovascular complications[1].
References	[1]. Noh H, et al. Beta 2-adrenergic receptor agonists are novel regulators of macrophage activation in diabetic renal and cardiovascular complications. Kidney Int. 2017 Jul;92(1):101-113. [2]. Ibrahim FA, et al. Highly sensitive spectrofluorimetric method for rapid determination of orciprenaline in biological fluids and pharmaceuticals. Luminescence. 2019 Feb;34(1):77-83.

Density	1.2±0.1 g/cm3
Boiling Point	417.5±40.0 °C at 760 mmHg
Molecular Formula	C₁₁H₁₇NO₃
Molecular Weight	211.258
Flash Point	179.7±17.9 °C
Exact Mass	211.120850
PSA	72.72000
LogP	0.13
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.579

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DO1800000

CHEMICAL NAME :: Benzyl alcohol, 3,5-dihydroxy-alpha-((isopropylamino)methyl)-

CAS REGISTRY NUMBER :: 586-06-1

LAST UPDATED :: 199709

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C11-H17-N-O3

MOLECULAR WEIGHT :: 211.29

WISWESSER LINE NOTATION :: QR CQ EYQ1MY

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 286 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Cardiac - arrhythmias (including changes in conduction) Vascular - BP elevation not characterized in autonomic section

REFERENCE :: AJMSA9 American Journal of the Medical Sciences. (Slack Inc., 6900 Grove Rd., Thorofare, NJ 08086) New series: V.1- 1841- Volume(issue)/page/year: 291,168,1986

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3370 mg/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 67200 ug/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >8130 mg/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 240 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - sympathomimetic

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,33,1972

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 295 mg/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4011258

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 86 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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 125 mg/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 30 mg/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3110 mg/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 81300 ug/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 8,353,1966 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 800 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: RDCNBM Reproduccion. (Madrid, Spain) V.1-7, 1974-83. Discontinued. Volume(issue)/page/year: 5,31,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5007 No. of Facilities: 35 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 476 (estimated) No. of Female Employees: 255 (estimated)