CAS 76-66-4|Rhynchophylline

Introduction：Basic information about CAS 76-66-4|Rhynchophylline, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

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

Common Name	Rhynchophylline
CAS Number	76-66-4	Molecular Weight	384.469
Density	1.2±0.1 g/cm3	Boiling Point	560.8±50.0 °C at 760 mmHg
Molecular Formula	C₂₂H₂₈N₂O₄	Melting Point	216°; mp 197-199° (Ban et al., loc. cit.)
MSDS	/	Flash Point	293.0±30.1 °C

Names

Name	Rhynchophylline
Synonym	More Synonyms

Rhynchophylline BiologicalActivity

Description	Rhyncholphylline, an alkaloid isolated from Uncaria, shows potent inhibition of lipopolysaccharide (LPS)-induced NO production in rat primary microglial cells.IC50 value:Target:In vitro: Rhyncholphylline effectively suppresses release of proinflammatory cytokines in LPS-activated microglial cells and the underling molecular mechanism for the inhibition of microglial activation; Attenuated LPS-induced production of proinflammatory cytokines such as TNF-α and IL-1β as well as NO in mouse N9 microglial cells [1]. Rhynchophylline exerts it protective action against ischemia-induced neuronal damage by preventing NMDA, muscarinic M1, and 5-HT2 receptors-mediated neurotoxicity during ischemia [3].In vivo: The neuroprotective effect of rhynchophylline was investigated in a stroke model. Following pMCAO, rhynchophylline treatment not only ameliorated neurological deficits, infarct volume and brain edema, but also increased claudin-5 and BDNF expressions (p < 0.05). Moreover, rhynchophylline could activate PI3K/Akt/mTOR signaling while inhibiting TLRs/NF-κB pathway [2].
Related Catalog	Signaling Pathways >>Others >>OthersNatural Products >>AlkaloidResearch Areas >>Others
References	[1]. Dan Yuan, et al. Anti-inflammatory effects of rhynchophylline and isorhynchophylline in mouse N9 microglial cells and the molecular mechanism. International Immunopharmacology Volume 9, Issues 13–14, December 2009, Pages 1549–1554 [2]. Houcai Huang, et al. Neuroprotective Effects of Rhynchophylline Against Ischemic Brain Injury via Regulation of the Akt/mTOR and TLRs Signaling Pathways. Molecules 2014, 19 (8): 11196-11210; doi:10.3390/molecules190811196 [3]. Tai-Hyun Kang, et al. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action. Life Sciences Volume 76, Issue 3, 3 December [4]. Kinzo Matsumoto, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: Behavioural and electrophysiological studies. European Journal of Pharmacology Volume 517, Issue 3, 11 July 2005, Pages 191–199

Description

Rhyncholphylline, an alkaloid isolated from Uncaria, shows potent inhibition of lipopolysaccharide (LPS)-induced NO production in rat primary microglial cells.IC50 value:Target:In vitro: Rhyncholphylline effectively suppresses release of proinflammatory cytokines in LPS-activated microglial cells and the underling molecular mechanism for the inhibition of microglial activation; Attenuated LPS-induced production of proinflammatory cytokines such as TNF-α and IL-1β as well as NO in mouse N9 microglial cells [1]. Rhynchophylline exerts it protective action against ischemia-induced neuronal damage by preventing NMDA, muscarinic M1, and 5-HT2 receptors-mediated neurotoxicity during ischemia [3].In vivo: The neuroprotective effect of rhynchophylline was investigated in a stroke model. Following pMCAO, rhynchophylline treatment not only ameliorated neurological deficits, infarct volume and brain edema, but also increased claudin-5 and BDNF expressions (p < 0.05). Moreover, rhynchophylline could activate PI3K/Akt/mTOR signaling while inhibiting TLRs/NF-κB pathway [2].

Related Catalog

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

References

[1]. Dan Yuan, et al. Anti-inflammatory effects of rhynchophylline and isorhynchophylline in mouse N9 microglial cells and the molecular mechanism. International Immunopharmacology Volume 9, Issues 13–14, December 2009, Pages 1549–1554

[2]. Houcai Huang, et al. Neuroprotective Effects of Rhynchophylline Against Ischemic Brain Injury via Regulation of the Akt/mTOR and TLRs Signaling Pathways. Molecules 2014, 19 (8): 11196-11210; doi:10.3390/molecules190811196

[3]. Tai-Hyun Kang, et al. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action. Life Sciences Volume 76, Issue 3, 3 December

[4]. Kinzo Matsumoto, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: Behavioural and electrophysiological studies. European Journal of Pharmacology Volume 517, Issue 3, 11 July 2005, Pages 191–199

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	560.8±50.0 °C at 760 mmHg
Melting Point	216°; mp 197-199° (Ban et al., loc. cit.)
Molecular Formula	C₂₂H₂₈N₂O₄
Molecular Weight	384.469
Flash Point	293.0±30.1 °C
Exact Mass	384.204895
PSA	67.87000
LogP	3.31
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.596
InChIKey	DAXYUDFNWXHGBE-UHFFFAOYSA-N
SMILES	CCC1CN2CCC3(C(=O)Nc4ccccc43)C2CC1C(=COC)C(=O)OC

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GN1600000

CHEMICAL NAME :: Corynoxan-16-carboxylic acid, 16,17-didehydro-17-methoxy-2-oxo-, methyl ester, (7- beta,16E,20-alpha)-

CAS REGISTRY NUMBER :: 76-66-4

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 :: 134 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 :: 105 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	S24/25
RTECS	GN1600000
HS Code	29399990

Synonyms

Methyl-(7β,16E,20α)-16-(methoxymethyliden)-2-oxocorynoxan-17-oat

Methyl (7β,16E,20α)-16-(methoxymethylene)-2-oxocorynoxan-17-oate

Methyl (16E)-16-(methoxymethylene)-2-oxocorynoxan-17-oate

Mitrinermine

Rhyncophylline

mitrinermin

Methyl (2E)-2-[(3R,6'R,7'S,8a'S)-6'-ethyl-2-oxo-1,2,2',3',6',7',8',8a'-octahydro-5'H-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyacrylate

Methyl (7β,16E,20α)-2-hydroxy-17-methoxy-1,2-didehydrocorynox-16-en-16-carboxylate

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-, methyl ester, (αE,3S,6'S,7'S,8'aS)-

methyl (7β,16E,20α)-16-(methoxymethylidene)-2-oxocorynoxan-17-oate

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-, methyl ester, (αE,3R,6'R,7'S,8'aS)-

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

rhynchophyllin

RHYNCHOLPHYLLINE

Recommended......