CAS 71771-90-9|Denopamine

Introduction：Basic information about CAS 71771-90-9|Denopamine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Denopamine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles24
7. Synonyms

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	/
MSDS	USA	Flash Point	267.6ºC
Symbol	GHS08	Signal Word	Warning

Names

Name	r(-)-denopamine
Synonym	More Synonyms

Denopamine BiologicalActivity

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	Research Areas >>Cardiovascular DiseaseSignaling Pathways >>GPCR/G Protein >>Adrenergic Receptor
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
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

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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