178803-51-5 Usage
Description
4-[(S)-[(2S,5R)-2,5-DIMETHYL-4-(2-PROPENYL)-1-PIPERAZINYL]PHENYLMETHYL]-N,N-DIETHYLBENZAMIDE is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers and various functional groups, which contribute to its potential biological activities and applications.
Uses
4-[(S)-[(2S,5R)-2,5-DIMETHYL-4-(2-PROPENYL)-1-PIPERAZINYL]PHENYLMETHYL]-N,N-DIETHYLBENZAMIDE is used as a selective δ-opioid receptor agonist for modulating the immune system.
Used in Pharmaceutical Industry:
4-[(S)-[(2S,5R)-2,5-DIMETHYL-4-(2-PROPENYL)-1-PIPERAZINYL]PHENYLMETHYL]-N,N-DIETHYLBENZAMIDE is used as a therapeutic agent for treating conditions related to the immune system, such as inflammatory responses and pain management. Its selective agonist activity on the δ-opioid receptor allows for targeted modulation of the immune system without affecting other opioid receptors, potentially reducing side effects and improving treatment outcomes.
Used in Research and Development:
In the field of research, 4-[(S)-[(2S,5R)-2,5-DIMETHYL-4-(2-PROPENYL)-1-PIPERAZINYL]PHENYLMETHYL]-N,N-DIETHYLBENZAMIDE serves as a valuable tool for studying the role of δ-opioid receptors in various biological processes. 4-[(S)-[(2S,5R)-2,5-DIMETHYL-4-(2-PROPENYL)-1-PIPERAZINYL]PHENYLMETHYL]-N,N-DIETHYLBENZAMIDE can be used to investigate the mechanisms underlying the immune system's response to opioids and to develop new therapeutic strategies for immune-related disorders.
Please note that the provided materials do not mention any specific uses for glycerol. The uses of glycerol are not directly related to the compound 4-[(S)-[(2S,5R)-2,5-DIMETHYL-4-(2-PROPENYL)-1-PIPERAZINYL]PHENYLMETHYL]-N,N-DIETHYLBENZAMIDE. If you have any specific information about the uses of glycerol in relation to this compound, please provide it, and I will be happy to include it in the answer.
Biological Activity
Potent and selective non-peptide δ -opioid receptor agonist (K i = 0.63 nM). Displays > 8000-fold selectivity over μ -opioid receptors and is centrally active following systemic administration in vivo .
Check Digit Verification of cas no
The CAS Registry Mumber 178803-51-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,8,8,0 and 3 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 178803-51:
(8*1)+(7*7)+(6*8)+(5*8)+(4*0)+(3*3)+(2*5)+(1*1)=165
165 % 10 = 5
So 178803-51-5 is a valid CAS Registry Number.
InChI:InChI=1/C27H37N3O/c1-6-18-29-19-22(5)30(20-21(29)4)26(23-12-10-9-11-13-23)24-14-16-25(17-15-24)27(31)28(7-2)8-3/h6,9-17,21-22,26H,1,7-8,18-20H2,2-5H3/t21-,22+,26+/m1/s1
178803-51-5Relevant articles and documents
Probes for narcotic receptor mediated phenomena. 23. Synthesis, opioid receptor binding, and bioassay of the highly selective δ agonist (+)-4- [(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]N,N- diethylbenzamide (SNC 80) and related novel nonpeptide δ opioid receptor ligands
Calderon, Silvia N.,Rice, Kenner C.,Rothman, Richard B.,Porreca, Frank,Flippen-Anderson, Judith L.,Kayakiri, Hiroshi,Xu, Heng,Becketts, Karen,Smith, Larren E.,Bilsky, Edward J.,Davis, Peg,Horvath, Robert
, p. 695 - 704 (2007/10/03)
The highly selective delta (δ) opioid receptor agonist SNC 80 [(+)-4- [(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N- diethylbenzamide, (+)-21] and novel optically pure derivatives were synthesized from the enantiomers of 1-allyl-trans-2,5-dimethylpiperazine (2). The piperazine (±)-2 was synthesized, and its enantiomers were obtained on a multigram scale in >99% optical purity by optical resolution of the racemate with the camphoric acids. The absolute configuration of (+)-2 was determined to be 2S,5R by X-ray analysis of the salt with (+)-camphoric acid. Since the chirality of the starting material was known, and the relative configuration of compounds (-)-21, (-)-22, and (+)-23 were obtained by single-crystal X- ray analysis, the assignment of the absolute stereochemistry of the entire series could be made. Radioreceptor binding studies in rat brain preparations showed that methyl ethers (+)-21 (SNC 80) and (-)-25 exhibited strong selectivity for rat δ receptors with low nanomolar affinity to 6 receptors and only micromolar affinity for rat mu (μ) opioid receptors. Compounds (- )-21, (-)-22, and (-)-23 showed micromolar affinities for δ opioid receptors. The unsubstituted derivative (+)-22 and the fluorinated derivative (-)-27 showed >2659- and >2105-fold δ/μ binding selectivity, respectively. The latter derivatives are the most selective ligands described in the new series. Studies with some of the compounds described in the isolated mouse vas deferens and guinea pig ileum bioassays revealed that all were agonists with different degrees of selectivity for the δ opioid receptor. These data show that (+)-21 and (+)-22 are potent δ receptor agonists and suggest that these compounds will be valuable tools for further study of the δ opioid receptor at the molecular level, including its function and role in analgesia and drug abuse.
