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Structure of JZL184
CAS No.: 1101854-58-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
JZL 184 is a potent and selective inhibitor of MAGL with IC50 of 8 nM and 4 μM for inhibition of MAGL and FAAH in mouse brain membranes respectively.
4.5
*For Research Use Only !
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 1101854-58-3 |
Formula : | C27H24N2O9 |
M.W : | 520.49 |
SMILES Code : | O=C(N1CCC(C(C2=CC=C(OCO3)C3=C2)(C4=CC=C(OCO5)C5=C4)O)CC1)OC6=CC=C([N+]([O-])=O)C=C6 |
MDL No. : | MFCD11976911 |
InChI Key : | SEGYOKHGGFKMCX-UHFFFAOYSA-N |
Pubchem ID : | 25021165 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301 |
Precautionary Statements: | P301+P310 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
Target |
|
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
GSC 528 cells | 1 μM | 24 hours | JZL184 significantly reduced the self-renewal capacity of GSC 528 cells. | PMC7293269 |
GSC X01 cells | 1 μM | 24 hours | JZL184 significantly reduced the self-renewal capacity of GSC X01 cells. | PMC7293269 |
Caco-2 cells | 5 µM | 6 hours | Silencing MGL in Caco-2 cells resulted in up-regulation of PPAR-α and PPAR-γ, and down-regulation of inflaμMatory markers Tnfα and Cox2. | PMC7317927 |
mouse brain membrane proteomes | 50 nM | 30 minutes | Near-complete blockade of MAGL activity | PMC2605181 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
mice | Parkinsonism model | oral | 2 mg kg−1 | once a week for 2 months | JZL184 prevented MPTP-induced dopaminergic neuronal loss in the substantia nigra and significantly attenuated dopamine reductions | PMC3249428 |
Mice | CaMKII αT286A/T286A mouse model | Intraperitoneal injection | 40 mg/kg | Once daily for 3 days | JZL-184 significantly depressed motor activity in CaMKII αT286A/T286A mice but not in WT littermates. | PMC3636998 |
mice | hepatic ischemia/reperfusion injury model | intraperitoneal injection | 10-80 mg | Once daily, during chemotherapy | JZL184 significantly attenuated hepatic ischemia/reperfusion injury by enhancing endocannabinoid signaling and reducing eicosanoid production. | PMC3608818 |
Mice | MAGL knockout mice | Intraperitoneal injection | 40 mg/kg | once, 1 hour before ischemia | To investigate the long-term effects of JZL184 on the endocannabinoid system in mice, the results showed that JZL184 led to a loss of analgesic activity and produced cross-tolerance to cannabinoid receptor agonists. | PMC2928870 |
Nude mice | GSC X01 xenograft model | Oral | 50 μg Betulinic acid + 3 μg BMP2 | single administration, lasting 4 weeks | JZL184 significantly reduced tumor mass and suppressed TAM infiltration. | PMC7293269 |
Mice | Stress susceptibility model | Systemic administration | 20 mg/kg | Once daily for 3 days | JZL184 significantly reduced stress-induced anxiety-like behavior by enhancing 2-AG signaling and promoted resilience after stress. | PMC5379055 |
Mice | Shank3B–/– mouse model | Intraperitoneal injection | PLX5622-formulated AIN-76A diet | 14 days | JZL184 pretreatment prevented the blue light delivery–dependent suppression of sociability in the 3-chamber SI test in ChR2-expressing animals but did not affect SI in YFP-expressing controls. | PMC7108917 |
Mice | Mdr2−/− mouse model | Dietary administration | 100 mg/kg | Daily for 5 to 9 months | JZL184, by inhibiting MGL activity, ameliorated biliary fibrosis and inflammation in Mdr2?/? mice, reduced serum ALT and AP levels, and decreased the expression of liver fibrosis markers. | PMC7317927 |
mice | intraperitoneal injection | 2 mg/kg/day TVB-3166, 100 mg/kg/day ABT-263 or ABT-199 | Once daily for 42 days | JZL184 significantly elevated brain 2-AG levels and induced CB1-dependent behavioral effects | PMC2605181 | |
Mice | Conditioned place preference (CPP) and self-administration models | Intraperitoneal injection | 3 mg/kg and 10 mg/kg | Once daily for 57 days | JZL184 significantly attenuates the rewarding effects of opioids without affecting their analgesic properties | PMC11606496 |
Tags: JZL 184 | JZL184 | JZL-184 | MAGL | Monoacylglycerol lipase | 2-Arachidonoylglycerol | hydrolysis | analgesia | antinociceptive | neurons | 1101854-58-3
Precautionary Statements-General | |
Code | Phrase |
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Code | Phrase |
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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. |
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P243 | Take precautionary measures against static discharge. |
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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: |
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P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
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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. |
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P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
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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. |
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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 |
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P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
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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 |
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H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
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H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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