156727-74-1

Basic information

• Product Name: SNC 80
• Synonyms: (+)-4-[(Ar)-alpha-((2s,5r)-4-allyl-2,5-dimethyl-1-piperazinyl)-3;4-[(R)-[(2S,5R)-2,5-Dimethyl-4-(2-propen-1-yl)-1-piperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide;NIH 10815;(+)-4-[(AR)-A-((2S,5R)-4-ALLYL-2,5-DIMETHYL-1-PIPERAZINYL)-3-METHOXYBENZYL]-N,N-DIETHYLBENZAM;(+)-4-[(AR)-A-((2S,5R)-4-ALLYL-2,5-DIMETHYL-1-PIPERAZINYL)-3-METHOXYBENZYL]-N,N-DIETHYLBENZAMIDE;(+)-4-[(AR)-ALPHA-((2S,5R)-4-ALLYL-2,5-DIMETHYL-1-PIPERAZINYL)-3-METHOXYBENZYL]-N,N-DIETHYLBENZAMIDE;SNC 80;(+)-4-[(αr)-α-((2s,5r)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-n,n-diethylbenzamide
• CAS NO: 156727-74-1
• Molecular Formula: C₂₈H₃₉N₃O₂
• Molecular Weight: 449.63
• Product Categories: Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Opioid receptor and opioid-like receptor
• Mol File: 156727-74-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 122-123°C
• Boiling Point: 564.8°Cat760mmHg
• Flash Point: 295.4°C
• Appearance: off-white/solid
• Density: 1.040
• Vapor Pressure: 8.83E-13mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Store at RT
• Solubility: DMSO: soluble
• PKA: 7.29±0.10(Predicted)
• Stability: Store in Freezer
• CAS DataBase Reference: SNC 80(CAS DataBase Reference)
• NIST Chemistry Reference: SNC 80(156727-74-1)
• EPA Substance Registry System: SNC 80(156727-74-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 156727-74-1(Hazardous Substances Data)

Usage

Description

SNC 80, a selective nonpeptide agonist of the δ-opioid receptor, is a crystalline solid with high potency and selectivity. It is over 2,000-fold less effective at the μ-opioid receptor and effectively activates μ/δ receptor heteromers. SNC 80 exhibits antinociceptive and pro-convulsant effects in vivo.

Uses

Used in Pharmaceutical Industry:
SNC 80 is used as a highly selective and potent non-peptide agonist for the δ-opioid receptor, which is over 2,000-fold selective over μ-opioid receptors. This high selectivity makes it a valuable compound for the development of drugs targeting the δ-opioid receptor.
Used in Research and Development:
In the field of neuroscience and pharmacology, SNC 80 is used as a research tool to study the role of nitric oxide synthase in peripheral antinociception mechanisms. Rats are administered SNC 80 to investigate its effects on pain relief and to better understand the underlying mechanisms.
Used in Pain Management:
SNC 80 is used as an antinociceptive agent, providing pain relief through its activation of the δ-opioid receptor. Its high selectivity and potency make it a potential candidate for the development of new pain management therapies.
Used in Convulsive Disorder Research:
Due to its pro-convulsant effects in vivo, SNC 80 is also used in the study of convulsive disorders and the development of treatments for conditions such as epilepsy. Researchers can use SNC 80 to investigate the underlying mechanisms of convulsions and develop targeted therapies.

Biological Activity

A highly selective and potent non-peptide δ -opioid agonist, 2000-fold selective over μ -opioid receptors.

Biochem/physiol Actions

SNC80 is a highly selective agonist of δ opioid receptor but also binds to μ-δ opioid receptor heteromers to produce antinociception in mice.2 It also acts as anti-depressant3, elicits dopamine-related behaviors and enhances behavioral responses to psychostimulants.4

InChI:InChI=1/C28H39N3O2/c1-7-17-30-19-22(5)31(20-21(30)4)27(25-11-10-12-26(18-25)33-6)23-13-15-24(16-14-23)28(32)29(8-2)9-3/h7,10-16,18,21-22,27H,1,8-9,17,19-20H2,2-6H3/t21-,22+,27-/m1/s1

Upstream product

• 186094-10-0 4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide 
• 155836-78-5 (-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 58287-77-7 N,N-diethyl-4-formylbenzamide 
• 619-66-9 4-Carboxybenzaldehyde 
• 82520-37-4 (4-methylphenyl)-(3-methoxyphenyl)methanone 
• 1711-05-3 m-anisoyl chloride 
• 108-88-3 toluene 
• 1027905-05-0 4-(3-Methoxy-benzoyl)-benzoyl chloride 
• 156727-76-3 4-(3-methoxybenzoyl)benzoic acid 
• 156727-77-4 N,N-diethyl-4-(3-methoxybenzoyl)benzamide 
• 186094-06-4 (±)-4-[hydroxy-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide 
• 2815-34-1 2,5-dimethyl-piperazine 

Downstream Products

• 155836-50-3 4-((alpha-R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide 
• 687996-30-1 (+)-4-[(αR)-α-((2S,5R)-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide 

Relevant articles and documents

METHOD OF TREATING PARKINSON'S DISEASE WITH DIARYLMETHYLPIPERAZINE COMPOUNDS EXHIBITING DELTA RECEPTOR AGONIST ACTIVITY

Compositions and methods for treatment of Parkinson's disease to reduce the negative side effects of the disease by administering a therapeutically effective diarylmethylpiperazine compound which exhibits delta opioid receptor agonist activity, and option

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

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.