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SNC-80

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From Wikipedia, the free encyclopedia

Opioid analgesic drug

Pharmaceutical compound

SNC-80
Clinical data

Other names	SNC-80
Identifiers
IUPAC name 4-[(R)-[(2S,5R)-4-allyl-2,5-dimethylpiperazin-1-yl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide
CAS Number	156727-74-1^N
PubChemCID	123924
IUPHAR/BPS	1611
ChemSpider	110453^Y
UNII	L842QB22SW
ChEBI	CHEBI:231727
ChEMBL	ChEMBL13470^Y
CompTox Dashboard(EPA)	DTXSID6045662
Chemical and physical data
Formula	C₂₈H₃₉N₃O₂
Molar mass	449.639 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N(CC)CC)c1ccc(cc1)[C@@H](N2C[C@H](N(C\C=C)C[C@@H]2C)C)c3cccc(OC)c3
InChI 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-/m1/s1^Y Key:KQWVAUSXZDRQPZ-UMTXDNHDSA-N^Y
^NY (what is this?) (verify)

SNC-80 is anopioid analgesic compound that selectively activates μ–δ opioid receptorheteromers^[1] and is used primarily in scientific research.^[2] Discovered in 1994, SNC-80 was a pioneering non-peptide compound regarded as a highly selective agonist for the δ-opioid receptor.^[3]

SNC-80 was the first non-peptide compound developed that was regarded as a highly selectiveagonist for theδ-opioid receptor.^[4]It has been shown to produce usefulanalgesic,^[5]antidepressant^[6] andanxiolytic effects in animal studies,^[7]^[8] but its usefulness is limited by producingconvulsions at high doses,^[9] and so SNC-80 is not used medically, although it is a useful compound in scientific research.

References

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^Metcalf MD, Yekkirala AS, Powers MD, Kitto KF, Fairbanks CA, Wilcox GL, Portoghese PS (July 2012)."The δ opioid receptor agonist SNC80 selectively activates heteromeric μ-δ opioid receptors".ACS Chemical Neuroscience.3 (7):505–9.doi:10.1021/cn3000394.PMC 3399572.PMID 22860219.
^Calderon SN, Coop A (2004). "SNC 80 and related delta opioid agonists".Current Pharmaceutical Design.10 (7):733–42.doi:10.2174/1381612043453054.PMID 15032699.
^Calderon SN, Rothman RB, Porreca F, Flippen-Anderson JL, McNutt RW, Xu H, et al. (July 1994). "Probes for narcotic receptor mediated phenomena. 19. Synthesis of (+)-4-[(alpha R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3- methoxybenzyl]-N,N-diethylbenzamide (SNC 80): a highly selective, nonpeptide delta opioid receptor agonist".Journal of Medicinal Chemistry.37 (14):2125–8.doi:10.1021/jm00040a002.PMID 8035418.
^Bilsky EJ, Calderon SN, Wang T, Bernstein RN, Davis P, Hruby VJ, et al. (April 1995). "SNC 80, a selective, nonpeptidic and systemically active opioid delta agonist".The Journal of Pharmacology and Experimental Therapeutics.273 (1):359–66.PMID 7714789.
^Gallantine EL, Meert TF (July 2005). "A comparison of the antinociceptive and adverse effects of the mu-opioid agonist morphine and the delta-opioid agonist SNC80".Basic & Clinical Pharmacology & Toxicology.97 (1):39–51.doi:10.1111/j.1742-7843.2005.pto_97107.x.PMID 15943758.
^Jutkiewicz EM, Rice KC, Traynor JR, Woods JH (November 2005)."Separation of the convulsions and antidepressant-like effects produced by the delta-opioid agonist SNC80 in rats".Psychopharmacology.182 (4):588–96.doi:10.1007/s00213-005-0138-9.PMC 1307499.PMID 16163520.
^Perrine SA, Hoshaw BA, Unterwald EM (April 2006)."Delta opioid receptor ligands modulate anxiety-like behaviors in the rat".British Journal of Pharmacology.147 (8):864–72.doi:10.1038/sj.bjp.0706686.PMC 1760715.PMID 16491101.
^Saitoh A, Kimura Y, Suzuki T, Kawai K, Nagase H, Kamei J (July 2004)."Potential anxiolytic and antidepressant-like activities of SNC80, a selective delta-opioid agonist, in behavioral models in rodents".Journal of Pharmacological Sciences.95 (3):374–80.doi:10.1254/jphs.FPJ04014X.PMID 15272214.
^Danielsson I, Gasior M, Stevenson GW, Folk JE, Rice KC, Negus SS (October 2006)."Electroencephalographic and convulsant effects of the delta opioid agonist SNC80 in rhesus monkeys".Pharmacology, Biochemistry, and Behavior.85 (2):428–34.doi:10.1016/j.pbb.2006.09.012.PMC 1820742.PMID 17112570.