CAS No. :	84-26-4
Formula :	C₁₈H₁₃N₃O
M.W :	287.32
SMILES Code :	O=C1C2=CC=CC=C2N=C3N1CCC4=C3NC5=CC=CC=C45
Synonyms :	Rutecarpine; NSC 258317
MDL No. :	MFCD00210551
InChI Key :	ACVGWSKVRYFWRP-UHFFFAOYSA-N
Pubchem ID :	65752

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280-P305+P351+P338

C4-2 cells	5 µM	24 hours	Rutaecarpine inhibits cell proliferation	Theranostics. 2020 Feb 10;10(8):3366-3381
LNCaP cells	5 µM	24 hours	Rutaecarpine inhibits cell proliferation	Theranostics. 2020 Feb 10;10(8):3366-3381
HepG2 cells	0.035, 0.35, 3.48, 34.80 µM	18 hours	RUT triggered promoters of ABCA1 and CLA-1 genes, increasing ABCA1 and SR-BI/CLA-1 expression	J Lipid Res. 2014 Aug;55(8):1634-47
HCT116 cells	5 µM	18 hours	To test the protective effect of RUT on H2O2-induced cytotoxicity, results showed that RUT pretreatment significantly increased the LD50 for H2O2-induced cell damage	Free Radic Biol Med. 2020 Feb 20;148:33-41
RAW 264.7 cells	10–40 µM	20 min pretreatment followed by 24 hours LTA stimulation	To evaluate the effect of Rutaecarpine on LTA-induced inflammatory responses in RAW 264.7 cells, results showed that Rutaecarpine inhibited NO production and the expression of iNOS, COX-2, and IL-1β without cytotoxicity.	Int J Mol Sci. 2022 May 24;23(11):5889
Human platelets	2.5–100 µM	20 minutes	Rutaecarpine showed no significant cytotoxicity to platelets at concentrations ranging from 2.5 to 100 μM.	Int J Mol Sci. 2021 Oct 15;22(20):11109
RAW264.7 cells	0.035, 0.35, 3.48, 34.80 µM	24 hours	RUT induced cholesterol efflux in RAW264.7 cells, reducing lipid accumulation	J Lipid Res. 2014 Aug;55(8):1634-47
Mouse chondrocytes	1, 2.5, 5, 10 µM	24 hours	To evaluate the anti-inflammatory, anti-catabolic, and pro-anabolic effects of Rutaecarpine on IL-1β-stimulated chondrocytes. Results showed that Rutaecarpine significantly inhibited the expression of inflammatory cytokines (COX2, IL-6, TNF-α), reduced the production of catabolic enzymes (MMP3, MMP13), and promoted the expression of anabolic enzymes (COL II, aggrecan, SOX9).	Int J Mol Med. 2023 Oct;52(4):97
RAW264.7 cells	1, 10, 25 µM	24 hours	To evaluate the inhibitory effect of Rutaecarpine on SARS-CoV-2-induced inflammatory responses, results showed that Rutaecarpine significantly reduced the mRNA levels of inflammatory cytokines.	Int J Mol Sci. 2023 Jan 1;24(1):762
HEK293T cells	1, 10, 25, 50, 100 µM	24 hours	To evaluate the inhibitory effect of Rutaecarpine on SARS-CoV-2 pseudovirus entry into cells, results showed that Rutaecarpine inhibited viral entry in a dose-dependent manner with a maximum inhibition rate of ~80%.	Int J Mol Sci. 2023 Jan 1;24(1):762
Primary mouse intestinal epithelial cells	10 µM and 20 µM	24 hours	To detect the expression of NRF2 target genes, results showed that RUT significantly induced the expression of NRF2 target gene mRNAs	Free Radic Biol Med. 2020 Feb 20;148:33-41
HepG2 cells	1.25 µM and 2.5 µM	24 hours	To detect NRF2 activation by luciferase reporter assay, results showed that RUT dose-dependently activated NRF2/ARE luciferase activity	Free Radic Biol Med. 2020 Feb 20;148:33-41
22Rv1 cells	5 µM	24 hours	Rutaecarpine selectively induces AR-V7 protein degradation	Theranostics. 2020 Feb 10;10(8):3366-3381
CL1-3 lung epithelial cells	5 µM	24 hours	Evaluate the inhibitory effect of F-RUT on TNF-α-induced COX-2 expression, results showed F-RUT was more effective than RUT in inhibiting COX-2 expression	Front Pharmacol. 2019 Feb 7;10:91
H460 lung epithelial cells	5 µM	24 hours	Evaluate the inhibitory effect of F-RUT on TNF-α-induced COX-2 expression, results showed F-RUT was more effective than RUT in inhibiting COX-2 expression	Front Pharmacol. 2019 Feb 7;10:91
Rat skeletal muscle cells	20–180 µM	24 hours	Promoted the phosphorylation of AMPK and ACC2, and increased glucose uptake	Acta Pharmacol Sin. 2016 Apr;37(4):483-96
Human endothelial EA.hy926 cells	1-10 µM	24 hours	To evaluate the effect of Rutaecarpine on endothelial cell viability and cytotoxicity. Results showed that Rutaecarpine at concentrations of 1 to 10 μM had no significant effect on cell viability or cytotoxicity.	Int J Mol Sci. 2021 Aug 30;22(17):9407
Human esophageal squamous cell carcinoma cell line CE81T/VGH	5–40 µM	24, 48, and 72 hours	To evaluate the effects of RTP on tumor cell growth. Results showed that RTP significantly inhibits CE81T/VGH cell growth in a dose- and time-dependent manner.	Int J Mol Sci. 2022 Mar 5;23(5):2843
Human platelets	1–5 µM	3 minutes	Rutaecarpine significantly inhibited collagen-induced platelet aggregation but had only a slight or no effect on platelets stimulated with other agonists (e.g., thrombin).	Int J Mol Sci. 2021 Oct 15;22(20):11109
Human endothelial EA.hy926 cells	10 µM	30 minutes	To investigate the effect of Rutaecarpine on eNOS phosphorylation. Results showed that Rutaecarpine significantly increased eNOS phosphorylation.	Int J Mol Sci. 2021 Aug 30;22(17):9407
PC12 cells	0.2, 0.4, 0.8 µM	48 hours	To investigate the protective effect of Rutaecarpine on H2O2-induced oxidative stress damage, results showed that Rutaecarpine significantly increased the survival rate of PC12 cells under oxidative stress, reduced ROS levels, and increased the activity of antioxidant enzymes CAT and SOD.	Front Pharmacol. 2022 Apr 12;13:807125
HCT116 cells	10 µM	6 hours	To detect NRF2 nuclear translocation by immunofluorescence, results showed that RUT significantly increased NRF2 nuclear translocation	Free Radic Biol Med. 2020 Feb 20;148:33-41

ICR mice	Microvascular thrombosis model	Intraperitoneal injection	0.7 and 1.5 mg/kg	Single dose	Rutaecarpine significantly prolonged the occlusion time of microvascular thrombosis in mice without affecting bleeding time.	Int J Mol Sci. 2021 Oct 15;22(20):11109
BALB/c mice	4T1 xenograft model	Intratumoral injection	10 μM, 50 μL/d	Once daily, tumor growth was monitored	Rutaecarpine significantly inhibited tumor growth and induced the differentiation of tumor cells into luminal-like structures.	J Transl Med. 2023 Aug 18;21(1):553
ApoE-deficient mice	High-fat diet-induced atherosclerosis model	Intragastric administration	10, 20, 40 mg/kg	Once daily for 8 weeks	RUT significantly reduced atherosclerotic lesion area, decreased plasma TC and LDL-C levels, and increased fecal cholesterol excretion	J Lipid Res. 2014 Aug;55(8):1634-47
Nude mice	22Rv1 xenograft models	Intraperitoneal injection	20 mg/kg/2d or 40 mg/kg/2d	Every 2 days for 15 days	Rutaecarpine significantly suppresses tumor growth	Theranostics. 2020 Feb 10;10(8):3366-3381
Nude mice BALB/cAnN	Xenograft model	Oral gavage	25 and 75 mg/kg	Twice weekly for six weeks	To confirm in vitro findings. Results showed that high-dose RTP significantly reduces tumor size, tumor weight, and PCNA protein expression.	Int J Mol Sci. 2022 Mar 5;23(5):2843
C57BL/6J mice	Destabilization of the medial meniscus (DMM) model	Intra-articular injection	25 mg/kg	Once per week for 8 weeks	To evaluate the therapeutic effects of Rutaecarpine on a mouse model of osteoarthritis. Results showed that Rutaecarpine significantly alleviated articular cartilage abrasion and proteoglycan depletion, reduced OARSI scores, and improved subchondral bone remodeling.	Int J Mol Med. 2023 Oct;52(4):97
Sprague-Dawley rats	Fat-fed, streptozotocin-treated rat model of hyperlipidemia and hyperglycemia	Oral	25 mg/kg/day	Once daily for 7 weeks	Ameliorated hyperlipidemia and hyperglycemia, reduced obesity and visceral fat accumulation, enhanced insulin sensitivity, decreased inflammatory cytokine levels, and improved pathological changes in livers and pancreases	Acta Pharmacol Sin. 2016 Apr;37(4):483-96
KM mice	Ethanol-induced acute gastric mucosal injury model	Intragastrically	450 and 900 μg/kg	Once daily for 3 consecutive days	Rutaecarpine significantly alleviated ethanol-induced gastric mucosal injury by modulating genes related to inflammation, oxidative stress and apoptosis	Front Pharmacol. 2020 Nov 26;11:600295
ICR mice	Acetaminophen-induced acute liver injury model	Oral	5 or 20 mg/kg	Once daily for 7 consecutive days	Rutaecarpine pretreatment significantly decreased acetaminophen-induced serum ALT/AST activities, hepatic malondialdehyde content, and prevented acetaminophen-induced hepatic glutathione depletion. Furthermore, CYP2E1 expression was decreased by rutaecarpine pretreatment in a dose-dependent manner.	Antioxidants (Basel). 2021 Jan 10;10(1):86
Zebrafish	LPS-induced inflammation model	Embryo media	5 μg/mL	24 hours	Evaluate the inhibitory effect of F-RUT on LPS-induced ROS generation, results showed F-RUT significantly suppressed ROS generation	Front Pharmacol. 2019 Feb 7;10:91
C57BL/6 mice	Controlled cortical impact (CCI)-induced TBI mouse model	Intraperitoneal injection	5, 10, 20 mg/kg	24 h and 30 min before surgery, and 2, 24, 48, and 72 h after surgery	To evaluate the neuroprotective effects of Rutaecarpine in TBI mice, results showed that Rutaecarpine significantly improved neurological dysfunction, reduced brain tissue edema and apoptosis, and enhanced antioxidant capacity.	Front Pharmacol. 2022 Apr 12;13:807125
C57BL/6J mice	DSS-induced colitis model	Oral gavage	80 mg/kg	Once daily until the end of the experiment	To test the protective effect of RUT on DSS-induced colitis, results showed that RUT significantly ameliorated DSS-induced colitis, dependent on the presence of NRF2	Free Radic Biol Med. 2020 Feb 20;148:33-41

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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CAS No.: 84-26-4

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CAS No.: 84-26-4

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed