MW 395.6 Da, Purity >99%. Competitive and selective anandamide transport inhibitor (IC50 = 1 μM). Active in vivo. Does not activate CB1 receptors or inhibit anandamide hydrolysis but has been shown to activate vanilloid receptors.
Images
Publications
Filter by
- Nature neuroscience 13:592-6002010Reduction in endocannabinoid tone is a homeostatic mechanism for specific inhibitory synapses.Applications:Unspecified applicationReactive species:Unspecified reactive speciesJimok Kim et. al.PubMed 20348918
Key facts
- CAS number
- 183718-77-6
- Purity
- > 99%
- Form
- Solid
- Molecular weight
- 395.6 Da
- Molecular formula
- C26H37NO2
- PubChem identifier
- 6604822
- Nature
- Synthetic
Alternative names
(R)-limonene 6-monooxygenase, (S)-limonene 6-monooxygenase, (S)-limonene 7-monooxygenase, 1,8-cineole 2-exo-monooxygenase, 15 LIPOXYGENASE RETICULOCYTE ARACHIDONATE, 15 LOX 1, 15 lipoxygenase 1, 15-LOX, 15-PGDH, 15-hydroxyprostaglandin dehydrogenase [NAD+], 70 kDa lysosomal alpha-glucosidase, AI838772, ALOX15, AW493413, Acid Maltase, Acid alpha glucosidase, Aglucosidase Alfa, Albendazole monooxygenase, Albendazole sulfoxidase, Alpha-glucosidase, Arachidonate 15-lipoxygenase, Arachidonate omega-6 lipoxygenase, CANN6, CB-R, CB1, CB1A, CB1K5, CB1R, CNR, CNR1_HUMAN, CNR2_HUMAN, CNRII, CP2C9_HUMAN, CP33, CP34, CP3A4_HUMAN, CPC9, CX 5, CYP2C, CYP2C10, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIIC9, CYPIIIA3, CYPIIIA4, Cannabinoid receptor 1, Cannabinoid receptor 2, Cannabinoid receptor 2 macrophage, Capsaicin receptor, Central cannabinoid receptor, Cytochrome P-450MP, Cytochrome P450 2C9, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 HLp, Cytochrome P450 MP-4, Cytochrome P450 MP-8, Cytochrome P450 NF-25, Cytochrome P450 PB-1, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450, family 2, subfamily C, polypeptide 9, Cytochrome P450-PCN1, DKFZp434K0220, FLJ11090, Glucocorticoid inducible P450, Glucosidase alpha, Glucosidase alpha acid, Glucosidase alpha acid (Pompe disease glycogen storage disease type II), HLP, Hpgd, Hydroxyprostaglandin dehydrogenase 15 (NAD), LOG15, LOX15_HUMAN, LYAG_HUMAN, Lysosomal Alpha-Glucosidase, MGC104252, MGC112732, MGC126680, MGC149605, MGC88320, Microsomal monooxygenase, NAD+ dependent 15 hydroxyprostaglandin dehydrogenase, NF 25, Nifedipine oxidase, OTRPC1, OTTHUMP00000016838, OTTHUMP00000020135, OTTHUMP00000214579, OTTHUMP00000218960, OTTHUMP00000219016, OTTHUMP00000219018, Osm-9-like TRP channel 1, P450 III steroid inducible, P450 MP, P450 PB 1, P450 PCN1, P450, family III, P450C3, P450IIC9, PGDH1, PGDH_HUMAN, PHOAR1, Prostaglandin dehydrogenase 1, Quinine 3-monooxygenase, RP24-311F12.2, S-mephenytoin 4-hydroxylase, SCAN1, SDR36C1, Short chain dehydrogenase/reductase family 36C member 1, TRPV1_HUMAN, TYDP, TYDP1_HUMAN, Taurochenodeoxycholate 6-alpha-hydroxylase, Transient receptor potential cation channel subfamily V member 1, Tyr-DNA phosphodiesterase 1, Tyrosyl-DNA phosphodiesterase 1, VR 1, Vanilloid receptor 1, Vanilloid receptor subtype 1, Xenobiotic monooxygenase, cytochrome P-450 S-mephenytoin 4-hydroxylase, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, flavoprotein-linked monooxygenase, hCB2, testis-dominant CNR2 isoform CB2
Recommended products
MW 395.6 Da, Purity >99%. Competitive and selective anandamide transport inhibitor (IC50 = 1 μM). Active in vivo. Does not activate CB1 receptors or inhibit anandamide hydrolysis but has been shown to activate vanilloid receptors.
Key facts
- CAS number
- 183718-77-6
- Purity
- > 99%
- Form
- Solid
- Molecular weight
- 395.6 Da
- Molecular formula
- C26H37NO2
- PubChem identifier
- 6604822
- Nature
- Synthetic
- Solubility
Soluble in DMSO to 50 mM.
Soluble in ethanol to 50 mM.
- Biochemical name
- N-(4-hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide
- Biological description
Competitive and selective anandamide transport inhibitor (IC50 = 1 μM). Active in vivo. Does not activate CB1 receptors or inhibit anandamide hydrolysis but has been shown to activate vanilloid receptors.
- Canonical SMILES
- CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC1=CC=C(C=C1)O
- Isomeric SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1=CC=C(C=C1)O
- InChI
- InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(29)27-24-20-22-25(28)23-21-24/h6-7,9-10,12-13,15-16,20-23,28H,2-5,8,11,14,17-19H2,1H3,(H,27,29)/b7-6-,10-9-,13-12-,16-15-
- InChIKey
- IJBZOOZRAXHERC-DOFZRALJSA-N
- IUPAC name
- (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- -20°C
- Appropriate long-term storage conditions
- -20°C
- Storage information
- Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
TRPV1 also known as the Transient Receptor Potential Vanilloid 1 is a protein that functions as an ion channel. It is activated by heat and capsaicin the compound that makes chili peppers hot. The protein has a mass of approximately 95 kDa. TRPV1 is widely expressed in sensory neurons where it plays a role in pain perception. Cannabinoid Receptor I (CB1) and Cannabinoid Receptor II (CB2) are part of the endocannabinoid system. They are G protein-coupled receptors located in the central nervous system and peripheral tissues. Cytochrome P450 3A4 abbreviated CYP3A4 is an enzyme known for its role in drug metabolism expressed mostly in the liver. TDP1 a tyrosyl-DNA phosphodiesterase facilitates DNA repair. CYP2C9 also contributes to drug metabolism similar to CYP3A4. 15-PGDH (15-hydroxyprostaglandin dehydrogenase) is involved in prostaglandin degradation and 15 Lipoxygenase 1 plays a role in fatty acid metabolism. GAA or Acid Alpha-Glucosidase is necessary for glycogen breakdown.
- Biological function summary
TRPV1 channels are central to detecting and regulating body temperature. They participate in inflammatory pain signaling. CB1 and CB2 receptors modulate neurotransmitter release and immune cell function. Both receptors have roles in the endocannabinoid system which includes endogenous cannabinoids like anandamide. CYP3A4 is critical for metabolizing xenobiotics and endogenous compounds affecting drug clearance rates. TDP1 helps in fixing DNA double-strand breaks working with other proteins in a complex. CYP2C9 is responsible for the oxidative metabolism of various substances including several drugs. 15-PGDH regulates prostaglandin levels and 15 Lipoxygenase 1 is involved in producing inflammatory mediators. GAA functions in lysosomes to convert glycogen to glucose.
- Pathways
TRPV1 is part of the pain and sensory pathways including those associated with inflammatory responses. It interacts with proteins like calcineurin in pain signaling pathways. CB1 and CB2 receptors are integral to cannabinoid signaling pathways. They regulate the endocannabinoid system and affect pathways related to mood and appetite. CYP3A4 and CYP2C9 enzymes participate in the metabolic pathways of drug detoxification. 15-PGDH participates in arachidonic acid metabolism relating to the pathway of prostaglandin degradation. 15 Lipoxygenase 1 associated with linoleic acid metabolism contributes to leukotriene production. GAA is significant in glycogen metabolism pathways related to energy release processes.
- Associated diseases and disorders
TRPV1 is associated with chronic pain conditions like neuropathy and inflammatory pain. Its dysregulation impacts pain signaling where calcineurin also plays an important role. CB1 and CB2 receptors are linked to disorders such as anxiety and multiple sclerosis due to their role in the endocannabinoid system affecting neurological functions. CYP3A4 and CYP2C9 alterations can influence drug reactions contributing to adverse drug events and vitamin D deficiency. 15-PGDH is relevant in cancer progression due to its role in prostaglandin metabolism. 15 Lipoxygenase 1 associates with inflammatory diseases like atherosclerosis. GAA deficiency causes Pompe disease a glycogen storage disorder impacting muscle and respiratory functions.
Product promise
We are dedicated to supporting your work with high quality reagents and we are here for you every step of the way should you need us.
In the unlikely event of one of our products not working as expected, you are covered by our product promise.
Full details and terms and conditions can be found here:
Terms & Conditions.
2 product images
Chemical Structure - AM404, Anandamide transport inhibitor (ab120095)
2D chemical structure image of ab120095, AM404, Anandamide transport inhibitor
Functional Studies - AM404, Anandamide transport inhibitor (ab120095)
SH-SY5Y cells were incubated at 37°C for 30 minutes with vehicle control (0 μM) and varied concentrations of AM404 (ab120095). Increased expression of c-Fos in SH-SY5Y cells correlates with an increase in AM404 concentration, as described in literature.
Whole cell lysates were prepared with RIPA buffer (containing protease inhibitors and sodium orthovanadate), 20 μg of each were loaded on the gel and the WB was run under reducing conditions. After transfer the membrane was blocked for an hour using 5% BSA before being incubated with ab7963 at 1 μg/ml and Anti-beta Actin antibody ab8227 at 1 μg/ml overnight at 4°C. Antibody binding was detected using an anti-rabbit antibody conjugated to HRP (Goat Anti-Rabbit IgG H&L (HRP) ab97051) at 1/10000 dilution and visualised using ECL development solution.
Downloads
Product protocols
- Visit the general protocols
- Visit troubleshooting
Please note: All products are 'FOR RESEARCH USE ONLY. NOT FOR USE IN DIAGNOSTIC OR THERAPEUTIC PROCEDURES'.
For licensing inquiries, please contact partnerships@abcam.com