AM404 structure
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Common Name | AM404 | ||
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CAS Number | 183718-77-6 | Molecular Weight | 395.578 | |
Density | 1.0±0.1 g/cm3 | Boiling Point | 579.4±50.0 °C at 760 mmHg | |
Molecular Formula | C26H37NO2 | Melting Point | N/A | |
MSDS | USA | Flash Point | 304.2±30.1 °C | |
Symbol |
GHS02, GHS07 |
Signal Word | Danger |
Use of AM404AM404, an inhibitor of endocannabinoid reuptake, blocks anandamide transport with IC50 values in the low micromolar range[1]. AM404 is able to relax rat isolated hepatic arteries contracted with Phenylephrine, with a pEC50 value of 7.4 (corresponding to an EC50 of 0.04 µM). Neuroprotective Effect[2]. |
Name | N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide |
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Synonym | More Synonyms |
Description | AM404, an inhibitor of endocannabinoid reuptake, blocks anandamide transport with IC50 values in the low micromolar range[1]. AM404 is able to relax rat isolated hepatic arteries contracted with Phenylephrine, with a pEC50 value of 7.4 (corresponding to an EC50 of 0.04 µM). Neuroprotective Effect[2]. |
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Related Catalog | |
In Vitro | AM404 reduces C6 glioma cell proliferation with IC50 values of 4.9 µM. AM404 non-specifically inhibit C6 glioma cell proliferation at concentrations used to block the cellular accumulation of the endocannabinoid anandamide[2]. Cell Viability Assay[2] Cell Line: Rat C6 glioma cells Concentration: 1, 3, 10 and 30 µM Incubation Time: 24, 48, 72 and 96 h Result: Produced a concentration-dependent reduction in cell proliferation that was seen with 24 h of exposure to 10 and 30 µM concentrations and after 48 h at 3 µM. The lowest concentration of AM404 tested, 1 µM, produced a significant, albeit small, reduction in cell proliferation at 72 h. |
In Vivo | AM404 (1-5 mg/kg, i.p.) exerts dose-dependent anxiolytic-like effects in the three models: elevated plus maze, defensive withdrawal and separation-induced ultrasonic vocalizations. Animal Model: Adult male Sprague-Dawley rats (250-300 g)[2] Dosage: 2.5-10 mg/kg Administration: Intraperitoneal (i.p.) Result: Caused a dose-dependent increase in anandamide levels in prefrontal cortex, hippocampus and thalamus. |
References |
Density | 1.0±0.1 g/cm3 |
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Boiling Point | 579.4±50.0 °C at 760 mmHg |
Molecular Formula | C26H37NO2 |
Molecular Weight | 395.578 |
Flash Point | 304.2±30.1 °C |
Exact Mass | 395.282440 |
PSA | 49.33000 |
LogP | 7.63 |
Vapour Pressure | 0.0±1.7 mmHg at 25°C |
Index of Refraction | 1.555 |
SECTION 1: Identification of the substance/mixture and of the company/undertaking Product identifiers Product name: N-(4-Hydroxyphenyl)-arachidonylamide REACH No.: A registration number is not available for this substance as the substance or its uses are exempted from registration, the annual tonnage does not require a registration or the registration is envisaged for a later registration deadline.
CAS-No.: 183718-77-6 Relevant identified uses of the substance or mixture and uses advised against Identified uses: Laboratory chemicals, Manufacture of substances SECTION 2: Hazards identification Classification of the substance or mixture Classification according to Regulation (EC) No 1272/2008 Flammable liquids (Category 2), H225 For the full text of the H-Statements mentioned in this Section, see Section 16. Classification according to EU Directives 67/548/EEC or 1999/45/EC F Highly flammableR11 For the full text of the R-phrases mentioned in this Section, see Section 16. Label elements Labelling according Regulation (EC) No 1272/2008 Pictogram Signal wordDanger Hazard statement(s) H225Highly flammable liquid and vapour. Precautionary statement(s) P210Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Supplemental Hazardnone Statements According to European Directive 67/548/EEC as amended. Hazard symbol(s)F Highly flammable R-phrase(s) R11Highly flammable. S-phrase(s) S16Keep away from sources of ignition - No smoking. Caution - this mixture contains a substance not yet fully tested. Other hazards - none SECTION 3: Composition/information on ingredients Mixtures Synonyms: AM404 Formula: C26H37NO2 C26H37NO2 Molecular Weight: 395,58 g/mol No components need to be disclosed according to the applicable regulations. For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16 SECTION 4: First aid measures Description of first aid measures General advice Consult a physician. Show this safety data sheet to the doctor in attendance. If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Most important symptoms and effects, both acute and delayed The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in section 11 Indication of any immediate medical attention and special treatment needed no data available SECTION 5: Firefighting measures Extinguishing media Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special hazards arising from the substance or mixture Carbon oxides, nitrogen oxides (NOx) Advice for firefighters Wear self contained breathing apparatus for fire fighting if necessary. Further information Use water spray to cool unopened containers. SECTION 6: Accidental release measures Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to form explosive concentrations. Vapours can accumulate in low areas. For personal protection see section 8. Environmental precautions Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations (see section 13). Reference to other sections For disposal see section 13. SECTION 7: Handling and storage Precautions for safe handling Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic charge. For precautions see section 2.2. Conditions for safe storage, including any incompatibilities Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: -20 °C Specific end use(s) A part from the uses mentioned in section 1.2 no other specific uses are stipulated SECTION 8: Exposure controls/personal protection Control parameters Components with workplace control parameters Exposure controls Appropriate engineering controls Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Personal protective equipment Eye/face protection Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Body Protection Impervious clothing., Flame retardant antistatic protective clothing, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Respiratory protection Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Control of environmental exposure Prevent further leakage or spillage if safe to do so. Do not let product enter drains. SECTION 9: Physical and chemical properties Information on basic physical and chemical properties a) AppearanceForm: liquid b) Odourno data available c) Odour Thresholdno data available d) pHno data available e) Melting point/freezingno data available point f) Initial boiling point and no data available boiling range g) Flash point14 °C - closed cup h) Evaporation rateno data available i) Flammability (solid, gas) no data available j) Upper/lowerno data available flammability or explosive limits k) Vapour pressureno data available l) Vapour densityno data available m) Relative densityno data available n) Water solubilityno data available o) Partition coefficient: n- no data available octanol/water p) Auto-ignitionno data available temperature q) Decompositionno data available temperature r) Viscosityno data available s) Explosive propertiesno data available t) Oxidizing propertiesno data available Other safety information no data available SECTION 10: Stability and reactivity Reactivity no data available Chemical stability Stable under recommended storage conditions. Possibility of hazardous reactions no data available Conditions to avoid Heat, flames and sparks. Extremes of temperature and direct sunlight. Incompatible materials Oxidizing agents, Alkali metals, Ammonia, Peroxides Hazardous decomposition products Other decomposition products - no data available In the event of fire: see section 5 SECTION 11: Toxicological information Information on toxicological effects Acute toxicity no data available Skin corrosion/irritation no data available Serious eye damage/eye irritation no data available Respiratory or skin sensitization no data available Germ cell mutagenicity no data available Carcinogenicity IARC:No component of this product present at levels greater than or equal to 0.1% is identified as probable, possible or confirmed human carcinogen by IARC. Reproductive toxicity no data available Specific target organ toxicity - single exposure no data available Specific target organ toxicity - repeated exposure no data available Aspiration hazard no data available Additional Information RTECS: Not available Central nervous system depression, narcosis, Nausea, Dizziness, Damage to the heart., To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly investigated. Heart - Irregularities - Based on Human Evidence SECTION 12: Ecological information Toxicity no data available Persistence and degradability no data available Bioaccumulative potential no data available Mobility in soil no data available Results of PBT and vPvB assessment PBT/vPvB assessment not available as chemical safety assessment not required/not conducted Other adverse effects no data available SECTION 13: Disposal considerations Waste treatment methods Product Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging Dispose of as unused product. SECTION 14: Transport information UN number ADR/RID: 1170IMDG: 1170IATA: 1170 UN proper shipping name ADR/RID: ETHANOL IMDG: ETHANOL IATA:Ethanol Transport hazard class(es) ADR/RID: 3IMDG: 3IATA: 3 Packaging group ADR/RID: IIIMDG: IIIATA: II Environmental hazards ADR/RID: noIMDG Marine Pollutant: noIATA: no Special precautions for user no data available SECTION 15 - REGULATORY INFORMATION N/A SECTION 16 - ADDITIONAL INFORMATION N/A |
Symbol |
GHS02, GHS07 |
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Signal Word | Danger |
Hazard Statements | H225-H319 |
Precautionary Statements | P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235 |
Personal Protective Equipment | Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter |
Hazard Codes | F: Flammable; |
Risk Phrases | R36/37/38 |
Safety Phrases | S7 |
RIDADR | UN 1170 3/PG 2 |
Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia.
Transl. Psychiatry 2 , e94, (2012) Cannabidiol is a component of marijuana that does not activate cannabinoid receptors, but moderately inhibits the degradation of the endocannabinoid anandamide. We previously reported that an elevatio... |
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The anandamide transport inhibitor AM404 reduces the rewarding effects of nicotine and nicotine-induced dopamine elevations in the nucleus accumbens shell in rats.
Br. J. Pharmacol. 165(8) , 2539-48, (2012) The fatty acid amide hydrolase inhibitor URB597 can reverse the abuse-related behavioural and neurochemical effects of nicotine in rats. Fatty acid amide hydrolase inhibitors block the degradation (an... |
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Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404.
Eur. J. Pharmacol. 408(2) , 161-8, (2000) The biological actions of the endogenous cannabinoid anandamide are terminated by carrier-mediated transport into neurons and astrocytes, followed by enzymatic hydrolysis. Anandamide transport is inhi... |
N-(4-Hydroxyphenyl)-arachidonylamide |
5,8,11,14-Eicosatetraenamide, N-(4-hydroxyphenyl)-, (5Z,8Z,11Z,14Z)- |
AM 404 |
(5Z,8Z,11Z,14Z)-N-(4-Hydroxyphenyl)icosa-5,8,11,14-tetraenamide |
N-(4-Hydroxyphenyl)arachidonylamide |
AM-404 |
AM404 |
(5Z,8Z,11Z,14Z)-N-(4-Hydroxyphenyl)-5,8,11,14-icosatetraenamide |