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S2812

Sigma-Aldrich

SNC80

≥98% (HPLC), solid

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Synonym(s):
(+)-4-[(αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide, SNC 80, SNC-80
Empirical Formula (Hill Notation):
C28H39N3O2
CAS Number:
156727-74-1
Molecular Weight:
449.63
MDL number:
MFCD00672673
PubChem Substance ID:
24278698
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: soluble

SMILES string

CCN(CC)C(=O)c1ccc(cc1)[C@H](N2C[C@H](C)N(CC=C)C[C@H]2C)c3cccc(OC)c3

InChI

1S/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?/m0/s1

InChI key

KQWVAUSXZDRQPZ-QNWUEUMSSA-N

Gene Information

human ... OPRD1(4985)
mouse ... Oprd1(18386)
rat ... Oprd1(24613) , Oprm1(25601)

Application

Rats were administered SNC80 to study the role of nitric oxide synthase in peripheral antinociception mechanism.5

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
SNC80 is a δ opioid receptor agonist.

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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S N Calderon et al.
Journal of medicinal chemistry, 40(5), 695-704 (1997-02-28)
The highly selective delta (delta) opioid receptor agonist SNC 80 [(+)-4- [(alpha R)-alpha-((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
Katia Befort et al.
Psychopharmacology, 214(4), 967-976 (2010-12-25)
Response inhibition, a primary symptom of many psychiatric disorders, is mediated through a complex neuropharmacological network that involves dopamine, serotonin, glutamate, noradrenaline, and cannabinoid mechanisms. Recently, we identified an opioidergic contribution to response inhibition by showing that deletion of mu
Chihiro Nozaki et al.
The Journal of pharmacology and experimental therapeutics, 342(3), 799-807 (2012-06-16)
N,N-diethyl-4-(5-hydroxyspiro[chromene-2,4'-piperidine]-4-yl) benzamide (ADL5859) and N,N-diethyl-3-hydroxy-4-(spiro[chromene-2,4'-piperidine]-4-yl)benzamide (ADL5747) are novel δ-opioid agonists that show good oral bioavailability and analgesic and antidepressive effects in the rat and represent potential drugs for chronic pain treatment. Here, we used genetic approaches to investigate molecular mechanisms
Akiyoshi Saitoh et al.
Behavioural brain research, 223(2), 271-279 (2011-05-14)
We previously reported that the δ opioid receptor (DOP) agonists SNC80 and TAN-67 produce potent antidepressant-like and antinociceptive effects in rodents. However, SNC80 produced convulsive effects. Recently, we succeeded in synthesizing a novel DOP agonist called KNT-127. The present study
Richard M van Rijn et al.
The Journal of pharmacology and experimental therapeutics, 344(1), 179-188 (2012-10-26)
Drugs targeting G-protein-coupled receptors (GPCRs) make up more than 25% of all prescribed medicines. The ability of GPCRs to form heteromers with unique signaling properties suggests an entirely new and unexplored pool of drug targets. However, current in vitro assays
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