SNC-80

SNC-80

Systematic (IUPAC) name
4-[(R)-[(2S,5R)-4-allyl-2,5-dimethylpiperazin-1-yl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide
Identifiers
CAS Number	156727-74-1
PubChem	CID 123924
IUPHAR/BPS	1611
ChemSpider	110453
ChEMBL	CHEMBL13470
Synonyms	SNC-80
Chemical data
Formula	C28H39N3O2
Molar mass	449.63 g/mol
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 Key:KQWVAUSXZDRQPZ-UMTXDNHDSA-N
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SNC-80 is an opioid analgesic drug that selectively activates μ–δ opioid receptor heteromers^[1] and is used in scientific research.^[2] It was discovered in 1994.^[3]

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

References

1. 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 Chem Neurosci 3 (7): 505–9. doi:10.1021/cn3000394. PMC 3399572. PMID 22860219.
2. Calderon SN, Coop A (2004). "SNC 80 and related delta opioid agonists". Curr. Pharm. Des. 10 (7): 733–42. doi:10.2174/1381612043453054. PMID 15032699.
3. Calderon SN, Rothman RB, Porreca F, Flippen-Anderson JL, McNutt RW, Xu H, Smith LE, Bilsky EJ, Davis P, Rice KC (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". J. Med. Chem. 37 (14): 2125–8. doi:10.1021/jm00040a002. PMID 8035418.
4. Bilsky EJ, Calderon SN, Wang T, Bernstein RN, Davis P, Hruby VJ, McNutt RW, Rothman RB, Rice KC, Porreca F (April 1995). "SNC 80, a selective, nonpeptidic and systemically active opioid delta agonist". J. Pharmacol. Exp. Ther. 273 (1): 359–66. PMID 7714789.
5. 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 Clin. Pharmacol. Toxicol. 97 (1): 39–51. doi:10.1111/j.1742-7843.2005.pto_07.x. PMID 15943758.
6. 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 (Berl.) 182 (4): 588–96. doi:10.1007/s00213-005-0138-9. PMC 1307499. PMID 16163520.
7. Perrine SA, Hoshaw BA, Unterwald EM (April 2006). "Delta opioid receptor ligands modulate anxiety-like behaviors in the rat". Br. J. Pharmacol. 147 (8): 864–72. doi:10.1038/sj.bjp.0706686. PMC 1760715. PMID 16491101.
8. 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". J. Pharmacol. Sci. 95 (3): 374–80. doi:10.1254/jphs.FPJ04014X. PMID 15272214.
9. 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". Pharmacol. Biochem. Behav. 85 (2): 428–34. doi:10.1016/j.pbb.2006.09.012. PMC 1820742. PMID 17112570.