Name: VESNARINONE
SKU: 81840-15-5

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Basic Information

Molecular Structure:
CAS No.:	81840-15-5
Name:	VESNARINONE
Article Data:	4

Formula:	C₂₂H₂₅N₃O₄
Molecular Weight:	395.458
Synonyms:	DRG-0210;vesnarinone;3,4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-quinoline;Vesnarinona [Spanish];6-[4-(3,4-dimethoxy-benzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril;Piteranometozine;Vesnarinonum [Latin];Arkin-Z;
Density:	1.246g/cm³
Melting Point:	238.1-239.5° (Tominaga); mp 238.1-239.8° (Shimizu)
Boiling Point:	678.3°C at 760 mmHg
Flash Point:	364°C
Safety:	Poison by intravenous route. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x.
PSA:	71.11000
LogP:	2.69180

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Chemistry

IUPAC Name: 6-[4-(3,4-Dimethoxybenzoyl)piperazin-1-yl]-3,4-dihydro-1H-quinolin-2-one
Synonyms of 3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2(1h)-quinolinone (CAS NO.81840-15-5) : 2(1H)-Quinolinone, 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydro- ; 3,4-Dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-quinolinone ; 6-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone ; 6-[4-(3,4-Dimethoxybenzoyl)piperazin-1-yl]-3,4-dihydroquinolin-2(1H)-one
CAS NO: 81840-15-5
Molecular Formula :C₂₂H₂₅N₃O₄
Molecular Weight :395.4516
Molecular Structure :
Index of Refraction: 1.601
Surface Tension: 50.1 dyne/cm
Density: 1.246 g/cm³
Flash Point: 364 °C
Enthalpy of Vaporization: 99.56 kJ/mol
Boiling Point: 678.3 °C at 760 mmHg
Vapour Pressure: 2.96E-18 mmHg at 25°C
Melting point :289 - 293 °C (decomposition).
Solubility% (25°C): Acetic acid 18.68, 14.19 ,Chloroform, benzyl alcohol 5.913, N-methyl -2 -PvP 3.407, 2.509 ,Dimethyl sulfoxide, sulfolane 1.229, 1.179 ,Dimethylformamide, dioxane ring 0.1653, 0.1151, Methanol, acetone, 0.06389, 0.04005 Ethanol, water .002086. pKa 2.86.

Uses

3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2(1h)-quinolinone (CAS NO.81840-15-5) is a cardiotonic agent. A mixed phosphodiesterase inhibitor and ion-channel modifier that has modest, dose-dependent, positive inotropic activity, but minimal negative chronotropic activity. 3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2(1h)-quinolinone (CAS NO.81840-15-5) improves ventricular performance most in patients with the worst degree of heart failure.

Production

Raw materials :1,4-Diazacyclohexane-->Formamide-->4-Methylanisole-->1,2,3,4-Tetrahydroquinolin-2-one
With 6 - Amino -3,4 - dihydro -2 (1H) - quinolinone as raw material. The 6 - Amino -3,4 - dihydro -2 (1H) - quinolinone (21.1g, 0.13mo1) and Double (Iraq-bromoethyl) amine hydrobromide (40.5g, 0.13mo1) dissolved in 150ml ethanol, reflux with mixing 8h. Cooling, adding Sodium carbonate (13.8g, 0.13mo1), and then reflux with mixining 8h. Cool to room temperature, filtered, collect precipitation, ethanol wash, ethanol - water, recrystallization,obtaining colorless needle-like crystals 26.4g 3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2(1h)-quinolinone (CAS NO.81840-15-5) , the yield was 64%.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	63300ug/kg (63.3mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
dog	LD50	oral	> 3gm/kg (3000mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
mouse	LD50	intraperitoneal	> 1200mg/kg (1200mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
mouse	LD50	intravenous	56300ug/kg (56.3mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: CYANOSIS	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
mouse	LD50	oral	> 7594mg/kg (7594mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
mouse	LD50	subcutaneous	> 1200mg/kg (1200mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES LIVER: OTHER CHANGES	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
rabbit	LD50	oral	> 3gm/kg (3000mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
rat	LD50	intraperitoneal	> 1200mg/kg (1200mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
rat	LD50	intravenous	79300ug/kg (79.3mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
rat	LD50	oral	> 7594mg/kg (7594mg/kg)	LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
rat	LD50	subcutaneous	> 3gm/kg (3000mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987.
women	TDLo	oral	16800ug/kg/14 (16.8mg/kg)	BLOOD: AGRANULOCYTOSIS	American Journal of Hematology. Vol. 44, Pg. 217, 1993.

Safety Profile

Poison by intravenous route. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x.