Denopamine

Modify Date: 2025-08-27 19:28:34

Denopamine Structure
Denopamine structure
Common Name Denopamine
CAS Number 71771-90-9 Molecular Weight 317.38
Density 1.177g/cm3 Boiling Point 518.8ºC at 760 mmHg
Molecular Formula C18H23NO4 Melting Point N/A
MSDS USA Flash Point 267.6ºC
Symbol GHS08
GHS08
Signal Word Warning

 Use of Denopamine


Denopamine ((R)-(-)-Denopamine) is an orally active, selective β1-adrenergic agonist. Denopamine prolongs survival in a murine model of congestive heart failure induced by viral myocarditis: suppression of tumor necrosis factor-α production in the heart. Cardiovascular effects[1].

 Names

Name r(-)-denopamine
Synonym More Synonyms

 Denopamine Biological Activity

Description Denopamine ((R)-(-)-Denopamine) is an orally active, selective β1-adrenergic agonist. Denopamine prolongs survival in a murine model of congestive heart failure induced by viral myocarditis: suppression of tumor necrosis factor-α production in the heart. Cardiovascular effects[1].
Related Catalog
In Vitro Denopamine (0.1-100 μM) suppresses LPS-induced TNF-α production in a concentration-dependent manner[1]. Cell Viability Assay[1] Cell Line: Murine spleen cells Concentration: 0, 0.1, 1, 10, 100 μM Incubation Time: 5 hours Result: Decreased TNF-α levels by 96.9±6.7%, 62.7±6.5%, 53.2±8.8%, and 40.3±1.5% at 0.1, 1, 10 and 100 μmol/L, respectively.
In Vivo Denopamine (14 μmol/kg per day; oral administration; for 14 days) significantly improves the survival of the animals, attenuates myocardial lesions, and suppresses TNF-α production in vivo[1]. The plasma concentration of Denopamine is 13.1±1.9 nmol/L at 1 h, 4.3±0.9 nmol/L at 2 h, 1.8±0.5 nmol/L at 3 h, and <0.6 nmol/L at 5 h after its administration. A single 14 μmol/kg dose of denopamine in mice produces a peak level at 1 h[1]. Animal Model: Four-week-old inbred male DBA/2 mice[1] Dosage: 14 μmol/kg per day Administration: Oral administration; 14 days Result: Treatment significantly improved the survival of the animals (14 of 25 (56%) treated, vs 5 of 25 (20%) control mice). At day 14, the survival rate of 57.1% (16 of 28 mice) in the treated group was significantly higher than the 33.3% (10 of 30 mice) survival rate in the control group. The survival rate from day 6 to day 14 was also significantly improved in the treated group (69.6%; 16 of 23 mice) versus the control group (45.5%; 10 of 22 mice, p < 0.05).
References

[1]. R Nishio, et al. Denopamine, a beta1-adrenergic agonist, prolongs survival in a murine model of congestive heart failure induced by viral myocarditis: suppression of tumor necrosis factor-alpha production in the heart. J Am Coll Cardiol. 1998 Sep;32(3):808-15.

 Chemical & Physical Properties

Density 1.177g/cm3
Boiling Point 518.8ºC at 760 mmHg
Molecular Formula C18H23NO4
Molecular Weight 317.38
Flash Point 267.6ºC
Exact Mass 317.16300
PSA 70.95000
LogP 2.66600
Index of Refraction 1.581
InChIKey VHSBBVZJABQOSG-INIZCTEOSA-N
SMILES COc1ccc(CCNCC(O)c2ccc(O)cc2)cc1OC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DA4795470
CHEMICAL NAME :
Benzenemethanol, alpha-(((2-(3,4-dimethoxyphenyl)ethyl)amino)methyl)-4 -hydroxy-, (R)-
CAS REGISTRY NUMBER :
71771-90-9
LAST UPDATED :
199406
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C18-H23-N-O4
MOLECULAR WEIGHT :
317.42
WISWESSER LINE NOTATION :
QR DYQ1M2R CO1 DO1

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 :
9369 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,751,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1785 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,751,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Sense Organs and Special Senses (Eye) - ptosis Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,751,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5672 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 19,544,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1651 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 19,544,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,700,1990 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6600 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,769,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
660 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,769,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
252 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,769,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
810 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,769,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
13 gm/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,769,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1300 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 32,769,1986

 Safety Information

Symbol GHS08
GHS08
Signal Word Warning
Hazard Statements H361
Precautionary Statements P281
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xn: Harmful;
Risk Phrases R62
Safety Phrases S22;S45;S36/S37/S39
RIDADR NONH for all modes of transport
RTECS DA4795470

 Articles24

More Articles
Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists.

Mol. Pharmacol. 56 , 875-885, (1999)

We examined the subtype-selective binding site of the beta-adrenergic receptors (betaARs). The beta(1)/beta(2)-chimeric receptors showed the importance of the second and seventh transmembrane domains ...

Regioselective glucuronidation of denopamine: marked species differences and identification of human udp-glucuronosyltransferase isoform.

Drug Metab. Dispos. 33(3) , 403-12, (2005)

Denopamine is one of the oral beta(1)-adrenoceptor-selective partial agonists. Denopamine glucuronide is the most abundant metabolite in human, rat, and dog urine when administered orally. Species dif...

Vascular responses to beta-adrenoceptor subtype-selective agonists with and without endothelium in rat common carotid arteries.

J. Auton. Pharmacol. 21(1) , 7-13, (2001)

1. Using the cannula inserting method, vasodilator responses to beta-adrenoceptor agonists (isoprenaline, denopamine and procaterol) were investigated in isolated and perfused rat common carotid arter...

 Synonyms

kalgut
(R)-4-{2-[2-(3,4-dimethoxy-phenyl)-ethylamino]-1-hydroxy-ethyl}-phenol
TA 064
MFCD00867122
Carguto
(R)-1-(4-Hydroxyphenyl)-2-(3,4-dimethoxyphenethylamino)ethanol
(-)-(R)-1-(p-hydroxyphenyl)-2-<(3,4-dimethoxyphenethyl)amino>ethanol
(-)-Denopamine
(R)-(-)-denopamine
(-)-(R)-1-(p-hydroxyphenyl)-2-<(3,4-dimehoxyphenethyl)amino>ethanol
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