157182-48-4 Usage
Description
S-2 METHANANDAMIDE, a potent agonist in the methanandamide series, is a chemical compound that exhibits significant affinity for the CB1 receptor. With a Ki value of 26 nM for the CB1 receptor, it demonstrates high potency and is less susceptible to FAAH inactivation. Additionally, it effectively inhibits the murine vas deferens twitch response, showcasing its potential in various applications.
Uses
Used in Pharmaceutical Industry:
S-2 METHANANDAMIDE is used as a CB1 receptor agonist for its high potency and affinity, making it a promising candidate for the development of new drugs targeting the endocannabinoid system. Its ability to inhibit the murine vas deferens twitch response with an IC50 value of 47 nM suggests potential applications in the treatment of various conditions related to the central nervous system.
Used in Research and Development:
S-2 METHANANDAMIDE is used as a research tool for studying the endocannabinoid system and its role in various physiological processes. Its high potency and selectivity for the CB1 receptor make it an invaluable compound for investigating the mechanisms of action and potential therapeutic applications of cannabinoids.
Used in Drug Design and Optimization:
S-2 METHANANDAMIDE is used as a lead compound for the design and optimization of new drugs targeting the CB1 receptor. Its high affinity and potency, as well as its resistance to FAAH inactivation, provide a solid foundation for the development of more effective and selective cannabinoid-based therapies.
Biological Activity
s-2 methanandamide is a cb1 receptor ligand.the cannabinoid receptor type 1 (cb1), is a g protein-coupled cannabinoid receptor located mainly in the central and peripheral nervous system. cb1 is also expressed in several cells relating to metabolism, such as muscle cells, fat cells, liver cells, and the digestive tract. the cb1 receptor has been involved in the maintenance of homeostasis in health and disease, preventing the development of excessive neuronal activity, reducing pain and other inflammatory symptoms. enhanced receptor expression has been identified in human hepatocellular carcinoma tumor samples and human prostate cancer cells [2].s-2 methanandamide was the second most potent cb1 receptor agonist in the methanandamide series. s-2 methanandamide activated the cb1 receptor with a ki value of 26 nm. s-2 methanandamide was less prone to faah inactivation. s-2 methanandamide inhibited the murine vas deferens twitch response with an ic50 value of 47 nm.
references
[1] abadji v, lin s, taha g, et al. (r)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability[j]. journal of medicinal chemistry, 1994, 37(12): 1889-1893.[2] howlett a c. cannabinoid receptor signaling[m]//cannabinoids. springer berlin heidelberg, 2005: 53-79.
Check Digit Verification of cas no
The CAS Registry Mumber 157182-48-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,7,1,8 and 2 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 157182-48:
(8*1)+(7*5)+(6*7)+(5*1)+(4*8)+(3*2)+(2*4)+(1*8)=144
144 % 10 = 4
So 157182-48-4 is a valid CAS Registry Number.
157182-48-4Relevant articles and documents
Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: A combination strategy to antitumor activity
Quintana, Paula G.,Garca Liares, Guadalupe,Chanquia, Santiago N.,Gorojod, Roxana M.,Kotler, Mnica L.,Baldessari, Alicia
, p. 518 - 528 (2016)
Twenty N-fatty acylamines from linolenic and arachidonic acids, fifteen of them new compounds, were obtained through Candida antarctica B lipase-catalyzed esterification and aminolysis reactions in very good yields and with high chemoselectivity. The optimal reaction conditions were achieved by studying the reaction parameters (temperature, E/S ratio, alcohol and alkanolamine/fatty acid ratio, time, solvent, free-solvent system, etc.). To identify ideal enzymatic methods for generating the alkanolamides we evaluated enzyme performance in three procedures: i) aminolysis of ethyl ester, ii) direct condensation between the fatty acid and the alkanolamine, and iii) a one-pot/two-step conversion of fatty acids into alkanolamides via in situ formation of the ethyl ester and subsequent aminolysis by the alkanolamine. The advantages noted with the enzymatic methodology, such as mild reaction conditions and low environmental impact, underscore biocatalysis as a convenient way to prepare the reported compounds. The cytotoxic activities of all compounds and mixtures of anandamide and its analogues were evaluated in rat glioma C6 cells. These studies reveal that some anandamide analogues enhance the antitumor effects of anandamide, suggesting their possible application as therapeutic tools in cancer treatment. Twenty N-fatty acylamines from linolenic and arachidonic acids were obtained by one-pot/two-step Candida antarctica B lipase-catalyzed esterification and aminolysis reactions in very good yields with high chemoselectivity. Cytotoxicity assays using rat glioma C6 cells revealed that some analogues enhanced the antitumor effects of anandamide (AEA), suggesting possible anticancer applications.
