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51-30-9 5984-95-2
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51-30-9

51-30-9 structure
51-30-9 structure
  • Name: Isoprenaline hydrochloride
  • Chemical Name: Isoprenaline hydrochloride
  • CAS Number: 51-30-9
  • Molecular Formula: C11H18ClNO3
  • Molecular Weight: 247.719
  • Catalog: API Respiratory medication Asthma
  • Create Date: 2018-05-22 08:00:00
  • Modify Date: 2024-01-02 18:03:56
  • Isoprenaline hydrochloride is a non-selective beta-adrenergic receptor agonist with potent peripheral vasodilator, bronchodilator, and cardiac stimulating activities.
Name Isoprenaline hydrochloride
Synonyms Isoproterenol hydrochloride
Pyrocatechol, 4-(1-hydroxy-2-(isopropylamino)ethyl)-, hydrochloride
Mistarel
4-(1-Hydroxy-2-(isopropylamino)ethyl)pyrocatechol hydrochloride
3,4-Dihydroxy-α-[(isopropylamino)methyl]benzyl alcohol hydrochloride
4-{1-hydroxy-2-[(1-methylethyl)amino]ethyl}benzene-1,2-diol hydrochloride
Isovon
euspiran
Isoprenaline HCl
1,2-benzenediol, 4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-, hydrochloride
1,2-Benzenediol, 4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-, hydrochloride (1:1)
EINECS 200-089-8
Saventrine IV
(±)-Isoproterenol hydrochloride
Suscardia
4-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,2-diol hydrochloride
isoprenaline
4-[1-Hydroxy-2-(isopropylamino)ethyl]-1,2-benzenediol hydrochloride (1:1)
Isomenyl
4-[1-Hydroxy-2-(isopropylamino)ethyl]benzene-1,2-diol hydrochloride (1:1)
isuprel
[3H]-Isoproterenol hydrochloride
Isoprenaline (hydrochloride)
DL-Isoproterenol hydrochloride
N-Isopropyl-DL-noradrenaline hydrochloride
Isoprenaline hydrochloride
4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol hydrochloride (1:1)
MFCD00012603
Isoproterenol HCl
proternol
DL-Isoprenaline hydrochloride
isadrine
Description Isoprenaline hydrochloride is a non-selective beta-adrenergic receptor agonist with potent peripheral vasodilator, bronchodilator, and cardiac stimulating activities.
Related Catalog
Target

Beta-adrenergic receptor[1]
In Vitro Isoprenaline (300 nM, 3 min) increases particulate cGMP- and cilostamide-inhibited, low-Km cAMP phosphodiesterase (cAMP-PDE) activity by about 100% in intact rat fat cells[1]. Isoprenaline inhibits insulin-stimulated glucose transport activity in rat adipocytes. Isoprenaline, in the absence of adenosine, promotes a time-dependent (t1/2 approximately 2 min) decrease in the accessibility of insulin-stimulated cell surface GLUT4 of > 50%, which directly correlated with the observed inhibition of transport activity[2]. Isoprenaline (5 nM and 10 mM) increases cyclic AMP levels and this effect is potentiated by cilostamide (10 mM), by rolipram, a cyclic AMP-specific PDE (PDE 4) inhibitor (10 mM) and by cyclic GMP-elevating agents (50 nM ANF or 30 nM SNP plus 100 nM DMPPO)[3]. Isoprenaline increases the transcriptional activity of Gi alpha-2 gene to 140% of the control value, whereas gene specific hybridization for Gs alpha remains unchanged[4]. Isoprenaline (20 nM) increases the amplitude of total iK and causes a negative shift of approximately 10 mV in the activation curve for iK, both in the absence and in the presence of 300 nM nisoldipine to block the L-type Ca2+ current. Isoprenaline (20 nM) increases the spontaneous pacemaker rate of sino-atrial node pacemaker cells by 16% in rabbit isolated pacemaker cells[5].
Cell Assay Cells are seeded in 24-well culture dishes at a density of 2 to 5×104 cells per well. Experiments are performed after 3 to 5 days in culture when cells has reached confluence. Culture medium is aspirated and replaced by 0.5 mL of PBS containing the pharmacological agents. Treatments are performed in quadruplicate at 37°C. The type 3, 4 and 5 PDE inhibitors cilostamide (10 gM), rolipram (10 pM) and DMPPO (10 gM), respectively, are incubated with cells for 30 min before addition of adenylate or guanylate cyclase activators. Cyclic GMP and cyclic AMP are respectively increased in RASMC by stimulation of particulate guanylate cyclase with ANF (50 nM for 10 min) or fl-adrenoceptors with isoprenaline (5 nm for 5 min). At the end of the incubation period, the medium is removed and intracellular cyclic nucleotides are extracted by two ethanolic (65%) ishes at 4°C for 5 min. Ethanolic extracts are pooled, evaporated to dryness by a Speed-Vac system. The dried extract is dissolved in a suitable amount of assay buffer and cyclic nucleotide levels are measured by scintillation proximity assay.
References

[1]. Degerman E, et al. Evidence that insulin and isoprenaline activate the cGMP-inhibited low-Km cAMP phosphodiesterase in rat fat cells by phosphorylation. Proc Natl Acad Sci U S A. 1990 Jan;87(2):533-7

[2]. Vannucci SJ, et al. Cell surface accessibility of GLUT4 glucose transporters in insulin-stimulated rat adipose cells. Modulation by isoprenaline and adenosine. Biochem J. 1992 Nov 15;288 (Pt 1):325-30.

[3]. Delpy E, et al. Effects of cyclic GMP elevation on isoprenaline-induced increase in cyclic AMP and relaxation in rat aortic smooth muscle: role of phosphodiesterase 3. Br J Pharmacol. 1996 Oct;119(3):471-8.

[4]. Muller FU, et al. Isoprenaline stimulates gene transcription of the inhibitory G protein alpha-subunit Gi alpha-2 in rat heart. Circ Res. 1993 Mar;72(3):696-700.

[5]. Lei M, et al. Modulation of delayed rectifier potassium current, iK, by isoprenaline in rabbit isolated pacemaker cells. Exp Physiol. 2000 Jan;85(1):27-35.
Density 1.324 g/cm3
Boiling Point 417.5ºC at 760 mmHg
Melting Point 165-175 °C (dec.)(lit.)
Molecular Formula C11H18ClNO3
Molecular Weight 247.719
Flash Point 179.7ºC
Exact Mass 247.097519
PSA 72.72000
LogP 2.32210
Storage condition Store at RT
Stability Stable, but may be air and light sensitive. Incompatible with strong oxidizing agents.
Water Solubility Soluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DO1925000
CHEMICAL NAME :
Benzyl alcohol, 3,4-dihydroxy-alpha-((isopropylamino)methyl)-, hydrochloride
CAS REGISTRY NUMBER :
51-30-9
LAST UPDATED :
199707
DATA ITEMS CITED :
23
MOLECULAR FORMULA :
C11-H17-N-O3.Cl-H
MOLECULAR WEIGHT :
247.75
WISWESSER LINE NOTATION :
QR BQ DYQ1MY1&1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2221 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
128 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
26900 ug/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1260 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
450 mg/kg
TOXIC EFFECTS :
Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
60 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
77 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
3070 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
27 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
930 mg/kg/31D-I
TOXIC EFFECTS :
Cardiac - other changes Cardiac - changes in heart weight Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
60 mg/kg/30D-I
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of salivary glands Endocrine - changes in adrenal weight Endocrine - changes in spleen weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
10 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
5 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
2500 ug/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
13 mg/L
REFERENCE :
EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 10(Suppl 10),1,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 82898 No. of Facilities: 1655 (estimated) No. of Industries: 3 No. of Occupations: 10 No. of Employees: 6062 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 82898 No. of Facilities: 649 (estimated) No. of Industries: 3 No. of Occupations: 8 No. of Employees: 18945 (estimated) No. of Female Employees: 8469 (estimated)
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant;
Risk Phrases R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS DO1925000
51-30-9 structure

51-30-9

~%

51-30-9 structure

51-30-9
Literature: Venter, Daniel P. Tetrahedron, 1991 , vol. 47, # 27 p. 5019 - 5024
Precursor  1

DownStream  3


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