198022-70-7

Basic information

• Product Name: AM 404
• Synonyms: N-(4-HYDROXYPHENYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE;N-(4-HYDROXYPHENYL)-5Z,8Z,11Z,14Z-EICOSATETRENAMIDE;N-(4-HYDROXYPHENYL)-ARACHIDONAMIDE;N-(4-HYDROXYPHENYL) ARACHIDONOYLAMIDE;N-(4-HYDROXYPHENYL)ARACHIDONYLAMIDE;ARACHIDONOYLAMIDE, N-(4-HYDROXYPHENYL);AM 404;N-(4-HYDROXYPHENYL)ARACHIDONYLAMIDE \ AN
• CAS NO: 198022-70-7
• Molecular Formula: C26H37NO2
• Molecular Weight: 395.58
• Product Categories: Cannabinoid receptor;Cannabinoid
• Mol File: 198022-70-7.mol
• Article Data: 0

Chemical Properties

• Appearance: /solution
• Storage Temp.: −20°C
• Solubility: ethanol: 24 mg/mL Photosensitive solution.
• Sensitive: Air Sensitive
• Stability: Stable for 1 year from date of purchase as supplied. Compound is subject to oxidation, store under inert gas to protect from exposure to air. Solutions in DMSO or ethanol may be stored under nitrogen or argon at -20° for up to 3 months.
• CAS DataBase Reference: AM 404(CAS DataBase Reference)
• NIST Chemistry Reference: AM 404(198022-70-7)
• EPA Substance Registry System: AM 404(198022-70-7)

Safety Data

• Hazard Codes: F,Xi
• Statements: 36/37/38
• Safety Statements: 7-16-36-26
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 1
• Hazardous Substances Data: 198022-70-7(Hazardous Substances Data)

Usage

Description

AM 404, also known as N-(4-hydroxyphenyl)arachidonamide, is a compound that inhibits anandamide transport with an IC50 of 1 μM. It does not inhibit anandamide amidase or activate cannabinoid receptors but instead activates vanilloid receptors. AM 404 has been shown to be active in vivo.

Uses

Used in Pharmaceutical Industry:
AM 404 is used as a pharmacological agent for its ability to inhibit anandamide transport and activate vanilloid receptors. This makes it a potential candidate for the development of new drugs targeting various medical conditions.
Used in Research Applications:
AM 404 is used as a research tool in the study of anandamide transport and vanilloid receptor activation. Its specific action on these targets allows researchers to better understand the underlying mechanisms and pathways involved in various physiological processes.
Used in Pain Management:
Due to its activation of vanilloid receptors, AM 404 may have potential applications in pain management. It could be used as a therapeutic agent for conditions involving pain, such as chronic pain or neuropathic pain, by modulating the pain signaling pathways through its interaction with vanilloid receptors.
Used in Neurological Disorders:
The inhibition of anandamide transport by AM 404 may have implications for the treatment of neurological disorders. It could be used as a therapeutic agent for conditions such as multiple sclerosis, Parkinson's disease, or Alzheimer's disease, where anandamide transport modulation may play a role in disease progression or symptom management.
Used in Cancer Research:
Although not explicitly mentioned in the provided materials, the activation of vanilloid receptors by AM 404 could potentially have applications in cancer research. It may be used as a tool to study the role of vanilloid receptors in cancer cell growth, proliferation, and apoptosis, potentially leading to the development of novel cancer therapies.

Biological Activity

Competitive and selective inhibitor of carrier-mediated anandamide transport (IC 50 = 1 μ M). Does not activate CB 1 receptors or inhibit anandamide hydrolysis but has been shown to activate native and cloned vanilloid receptors (pEC 50 = 7.4). Active in vivo . Also available in water soluble emulsion (N-(4-Hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide ).

References

1) Calignano?et al. (1997),?Potentiation of anandamide hypotension by the transport inhibitor AM404; Eur. J. Pharmacol.,?337?R1 2) Beltramo?et al. (1997), Functional role of high-affinity anandamide transport, as revealed by selective inhibition; Science,?277?1094 3) Zygmunt?et al. (2000),?The anandamide inhibitor AM404 activates vanilloid receptors: Eur. J. Pharmacol.?396?39