CAS 6859-01-4|Isorhyncophylline

Introduction：Basic information about CAS 6859-01-4|Isorhyncophylline, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

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

Common Name	Isorhyncophylline
CAS Number	6859-01-4	Molecular Weight	384.47
Density	1.4±0.1 g/cm3	Boiling Point	447.6±25.0 °C at 760 mmHg
Molecular Formula	C₂₂H₂₈N₂O₄	Melting Point	114ºC
MSDS	/	Flash Point	224.5±23.2 °C

Names

Name	isorhynchophylline
Synonym	More Synonyms

Isorhyncophylline BiologicalActivity

Description	Isorhynchophylline (IRN), an alkaloid isolated from Uncaria rhynchophylla, possesses the effects of lowered blood pressure, vasodilatation and protection against ischemia-induced neuronal damage.IC50 value:Target:In vitro: Isorhynchophylline concentration-dependently inhibited the platelet-derived growth factor (PDGF)-BB-induced proliferation of PASMCs. Fluorescence-activated cell-sorting analysis showed that isorhynchophylline caused G0/G1 phase cell cycle arrest [2]. Isorhynchophylline can significantly attenuate the cardiomyocyte hypertrophy induced by AngⅡ [3].In vivo: Isorhynchophylline significantly improved spatial learning and memory function in the D-gal-treated mice. Isorhynchophylline significantly increased the level of glutathione (GSH) and the activities of superoxide dismutase (SOD) and catalase (CAT), while decreased the level of malondialdehyde (MDA) in the brain tissues of the D-gal-treated mice [1]. Isorhynchophylline prevented monocrotaline induced pulmonary arterial hypertension in rats, as assessed by right ventricular (RV) pressure, the weight ratio of RV to (left ventricular+septum) and RV hypertrophy. Isorhynchophylline significantly attenuated the percentage of fully muscularized small arterioles, the medial wall thickness, and the expression of smooth muscle α-actin (α-SMA) and proliferating cell nuclear antigen (PCNA) [2].
Related Catalog	Signaling Pathways >>Others >>OthersNatural Products >>AlkaloidResearch Areas >>Others
References	[1]. Yan-Fang Xian, et al. Isorhynchophylline improves learning and memory impairments induced by D-galactose in mice. Neurochemistry International Volume 76, October 2014, Pages 42–49 [2]. Guo H, et al. Isorhynchophylline protects against pulmonary arterial hypertension and suppresses PASMCs proliferation. Biochem Biophys Res Commun. 2014 Jul 18;450(1):729-34. [3]. LI Qiang, et al. Inhibitory effect of isorhynchophylline on cardiomyocyte hypertrophy induced by angiotensinⅡ. West China JOurnal of Pharmaceutical Sciences, 2013-05

Description

Isorhynchophylline (IRN), an alkaloid isolated from Uncaria rhynchophylla, possesses the effects of lowered blood pressure, vasodilatation and protection against ischemia-induced neuronal damage.IC50 value:Target:In vitro: Isorhynchophylline concentration-dependently inhibited the platelet-derived growth factor (PDGF)-BB-induced proliferation of PASMCs. Fluorescence-activated cell-sorting analysis showed that isorhynchophylline caused G0/G1 phase cell cycle arrest [2]. Isorhynchophylline can significantly attenuate the cardiomyocyte hypertrophy induced by AngⅡ [3].In vivo: Isorhynchophylline significantly improved spatial learning and memory function in the D-gal-treated mice. Isorhynchophylline significantly increased the level of glutathione (GSH) and the activities of superoxide dismutase (SOD) and catalase (CAT), while decreased the level of malondialdehyde (MDA) in the brain tissues of the D-gal-treated mice [1]. Isorhynchophylline prevented monocrotaline induced pulmonary arterial hypertension in rats, as assessed by right ventricular (RV) pressure, the weight ratio of RV to (left ventricular+septum) and RV hypertrophy. Isorhynchophylline significantly attenuated the percentage of fully muscularized small arterioles, the medial wall thickness, and the expression of smooth muscle α-actin (α-SMA) and proliferating cell nuclear antigen (PCNA) [2].

Related Catalog

Signaling Pathways >>Others >>OthersNatural Products >>AlkaloidResearch Areas >>Others

References

[1]. Yan-Fang Xian, et al. Isorhynchophylline improves learning and memory impairments induced by D-galactose in mice. Neurochemistry International Volume 76, October 2014, Pages 42–49

[2]. Guo H, et al. Isorhynchophylline protects against pulmonary arterial hypertension and suppresses PASMCs proliferation. Biochem Biophys Res Commun. 2014 Jul 18;450(1):729-34.

[3]. LI Qiang, et al. Inhibitory effect of isorhynchophylline on cardiomyocyte hypertrophy induced by angiotensinⅡ. West China JOurnal of Pharmaceutical Sciences, 2013-05

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	447.6±25.0 °C at 760 mmHg
Melting Point	114ºC
Molecular Formula	C₂₂H₂₈N₂O₄
Molecular Weight	384.47
Flash Point	224.5±23.2 °C
PSA	78.87000
LogP	1.90
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.677
InChIKey	DAXYUDFNWXHGBE-VKCGGMIFSA-N
SMILES	CCC1CN2CCC3(C(=O)Nc4ccccc43)C2CC1C(=COC)C(=O)OC

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GN1605000

CHEMICAL NAME :: Corynoxan-16-carboxylic acid, 16,17-didehydro-17-methoxy-2-oxo-, methyl ester, (16E,20-alpha)-

CAS REGISTRY NUMBER :: 6859-01-4

LAST UPDATED :: 198909

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C22-H28-N2-O4

MOLECULAR WEIGHT :: 384.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 217 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 94,17,1989

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 80 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 94,17,1989

Safety Information

Safety Phrases	24/25

Synonyms

7-Isorhynchophylline

5-Methoxyindole-3-carboxylic Acid Hydrate

7-Isorhyncophylline

5-Methoxyindole-3-Carboxylic Acid

(16E,20α)-17-Methoxy-2-oxocorynox-16-en-16-carboxylic acid

Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, (αE,3S,6'R,7'S,8'aS)-

Isorhyncophylline

5-methoxyindole-2-carboxylic acid

1H-Indole-3-carboxylic acid, 5-methoxy-

5-Methoxy-1H-indole-3-carboxylic acid

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