CAS Number94421-68-8
Synonymsarachidonic acid ethanolamide; MFCD00153766; (5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-icosatetraenamide; N-arachidonoylethanolamide; N-arachidonoylethanolamine; arachidonylethanolamide; 5,8,11,14-Eicosatetraenoylethanolamide; N-Arachidonoyl-2-hydroxyethylamide; N-arachidonoyl ethanolamine; arachidonoylethanolamide; Arachidonoyl-EA; (5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)icosa-5,8,11,14-tetraenamide
Molecular FormulaC22H37NO2
Molecular Weight347.53
Purity≥97.0 (TLC)%
Density0.9±0.1 g/cm3
Boiling Point522.3±50.0 °C at 760 mmHg
Appearanceoil
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 94421-68-8 |
| Catalog No. | 2A-9060642 |
| Chinese Name | 花生四希酸乙醇胺 |
| Synonyms | arachidonic acid ethanolamide; MFCD00153766; (5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-icosatetraenamide; N-arachidonoylethanolamide; N-arachidonoylethanolamine; arachidonylethanolamide; 5,8,11,14-Eicosatetraenoylethanolamide; N-Arachidonoyl-2-hydroxyethylamide; N-arachidonoyl ethanolamine; arachidonoylethanolamide; Arachidonoyl-EA; (5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)icosa-5,8,11,14-tetraenamide |
| Molecular Formula | C22H37NO2 |
| Molecular Weight | 347.53 |
| Purity | ≥97.0 (TLC) |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 522.3±50.0 °C at 760 mmHg |
| Appearance | oil |
| Water Solubility | ethanol: soluble |
| Storage Condition | Store airtight in a cool, dry warehouse. Refrigera |
| Application | Anandamide is a central nervous system immunomodulator that acts not only through cannabinoid receptors (CB1 and CB2) but also through other targets such as GPR18/GPR55. |
| HTC | 2924199090 |
| PubChem ID | 24890438 |
| MDL Number | MFCD00153766 |
| SMILES | O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)NCCO |
| InChI | 1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15- |
| InChI Key | LGEQQWMQCRIYKG-DOFZRALJSA-N |
| NACRES Code | NA.25 |
| UNSPSC | 12352211 |
| Hazard Symbols | transportation |
| MSDS | msds/60642_1_94421_68_8.pdf |
| Bioactivity | Anandamide is an immune modulator in the central nervous system acts via not only cannabinoid receptors (CB1 and CB2) but also other targets (e.g., GPR18/GPR55). Related Catalog Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Signaling Pathways >> GPCR/G Protein >> GPR55 Research Areas >> Inflammation/Immunology Natural Products >> Others Target CB1 Receptor CB2 Receptor GPR18/GPR55 Human Endogenous Metabolite In Vitro Anandamide, acting via CB2 receptors, alleviates lipopolysaccharide (LPS)-induced neuroinflammation in rat primary microglial cultures. The endocannabinoid system modulates both neuronal and immune functions through two protein-coupled cannabinoid receptors (CB1 and CB2), although endocannabinoids, especially Anandamide (AEA), can activate numerous other receptors like PPARS, TRPV1, and GPR18/GPR55[1]. In Vivo Anandamide is an endocannabinoid binding both CB1R and CB2R. To evaluate the impact of CBR activation on whole-body glucose homeostasis, glucose tolerance is assessed after a single intraperitoneal Anandamide injection (10 mg/kg). The increase in glycemia in response to glucose ingestion is considerably smaller in mice treated with Anandamide compared with control, and this is associated with an improvement of glucose tolerance as illustrated by the AUC0-2h calculations[2]. Animal Admin Mice[2] Eleven-week-old C57BL/6J male mice and global CB1R-/- mice are housed individually on a 12/12-h light/dark schedule at 22-23°C with ad libitum access to water and food. A group of mice is subject to a high-fat diet (30% lard). After 16 weeks of diet, animals with a weight gain less than +10 g compared with controls are excluded from the study. Diet-induced obesity (DIO) mice (39.1±1.1 vs. 27.3±0.9 g, DIO vs. control) are glucose intolerant and insulin resistant. On the day of each experiment, food is removed from the cages for 6 h (from 8:00 A.M. to 2:00 P.M.). Anandamide is administered intraperitoneally at 10 mg/kg. In control experiments, animals are injected with vehicle (4% DMSO/1% Tween 80)[2]. References [1]. Malek N, et al. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast. 2015;2015:130639. [2]. Troy-Fioramonti S, et al. Acute activation of cannabinoid receptors by Anandamide reduces gastrointestinal motility and improves postprandial glycemia in mice. Diabetes. 2015 Mar;64(3):808-18. Chemical & Physical Properties Density 0.9±0.1 g/cm3 Boiling Point 522.3±50.0 °C at 760 mmHg Molecular Formula C22H37NO2 Molecular Weight 347.535 Flash Point 269.7±30.1 °C Exact Mass 347.282440 PSA 49.33000 LogP 5.66 Vapour Pressure 0.0±3.1 mmHg at 25°C Index of Refraction 1.504 InChIKey LGEQQWMQCRIYKG-DOFZRALJSA-N SMILES CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO Storage condition −20°C Water Solubility ethanol: soluble |
| Use of | Properties Articles98 Name anandamide Synonym More Synonyms Anandamide Biological Activity Related Catalog Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Signaling Pathways >> GPCR/G Protein >> GPR55 Research Areas >> Inflammation/Immunology Natural Products >> Others CB1 Receptor CB2 Receptor Human Endogenous Metabolite References [1]. Malek N, et al. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast. 2015;2015:130639. [2]. Troy-Fioramonti S, et al. Acute activation of cannabinoid receptors by Anandamide reduces gastrointestinal motility and improves postprandial glycemia in mice. Diabetes. 2015 Mar;64(3):808-18. Chemical & Physical Properties Molecular Formula C22H37NO2 Exact Mass 347.282440 PSA 49.33000 Index of Refraction 1.504 InChIKey LGEQQWMQCRIYKG-DOFZRALJSA-N SMILES CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO Water Solubility ethanol: soluble |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 30.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 United Nations number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special precautions No data available The above information is believed to be correct, but is not all-inclusive and should be used as a guide only. The information in this document is based on our current knowledge and is Correct safety instructions apply to this product. This information does not represent a warranty as to the properties of this product. See reverse side of invoice or packing slip. |
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