| Revision as of 13:26, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 449560266 of page SNC-80 for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 20:42, 23 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenol ethers; added Category:3-Methoxyphenyl compounds using HotCat |
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{{Short description|Opioid analgesic drug}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 430684455 |
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| verifiedrevid = 464385560 |
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| IUPAC_name = 4-(3-methoxyphenyl)methyl]-''N,N''-diethylbenzamide |
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| IUPAC_name = 4-(3-methoxyphenyl)methyl]-''N,N''-diethylbenzamide |
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| image = SNC-80.svg |
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| image = SNC-80 Structure.svg |
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| width = 220 |
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| width = |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| legal_US = |
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| legal_US = |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 156727-74-1 --> |
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| CAS_number = 156727-74-1 |
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| ATC_prefix = |
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| ATC_prefix = |
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| ATC_suffix = |
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| ATC_suffix = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = L842QB22SW |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 110453 |
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| ChemSpiderID = 110453 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 13470 |
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| ChEMBL = 13470 |
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| ChEBI = 231727 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=28 | H=39 | N=3 | O=2 |
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| C=28 | H=39 | N=3 | O=2 |
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| molecular_weight = 449.63 g/mol |
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| smiles = O=C(N(CC)CC)c1ccc(cc1)(N2C(N(C\C=C)C2C)C)c3cccc(OC)c3 |
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| smiles = O=C(N(CC)CC)c1ccc(cc1)(N2C(N(C\C=C)C2C)C)c3cccc(OC)c3 |
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| 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 |
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| InChIKey = KQWVAUSXZDRQPZ-UMTXDNHDBD |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| synonyms = SNC-80 |
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| synonyms = SNC-80 |
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}} |
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'''SNC-80''' is an ] ] compound that selectively activates μ–δ opioid receptor ]<ref name="pmid22860219">{{cite journal |vauthors=Metcalf MD, Yekkirala AS, Powers MD, Kitto KF, Fairbanks CA, Wilcox GL, Portoghese PS |date=July 2012 |title=The δ opioid receptor agonist SNC80 selectively activates heteromeric μ-δ opioid receptors |journal=ACS Chemical Neuroscience |volume=3 |issue=7 |pages=505–9 |doi=10.1021/cn3000394 |pmc=3399572 |pmid=22860219}}</ref> and is used primarily in scientific research.<ref name="pmid15032699">{{cite journal |vauthors=Calderon SN, Coop A |year=2004 |title=SNC 80 and related delta opioid agonists |journal=Current Pharmaceutical Design |volume=10 |issue=7 |pages=733–42 |doi=10.2174/1381612043453054 |pmid=15032699}}</ref> Discovered in 1994, SNC-80 was a pioneering non-peptide compound regarded as a highly selective agonist for the δ-opioid receptor.<ref name="pmid8035418">{{cite journal |display-authors=6 |vauthors=Calderon SN, Rothman RB, Porreca F, Flippen-Anderson JL, McNutt RW, Xu H, Smith LE, Bilsky EJ, Davis P, Rice KC |date=July 1994 |title=Probes for narcotic receptor mediated phenomena. 19. Synthesis of (+)-4--N,N-diethylbenzamide (SNC 80): a highly selective, nonpeptide delta opioid receptor agonist |journal=Journal of Medicinal Chemistry |volume=37 |issue=14 |pages=2125–8 |doi=10.1021/jm00040a002 |pmid=8035418}}</ref> |
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SNC-80 was the first non-] compound developed that was regarded as a highly selective ] for the ] ].<ref name="pmid7714789">{{cite journal | vauthors = Bilsky EJ, Calderon SN, Wang T, Bernstein RN, Davis P, Hruby VJ, McNutt RW, Rothman RB, Rice KC, Porreca F | display-authors = 6 | title = SNC 80, a selective, nonpeptidic and systemically active opioid delta agonist | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 273 | issue = 1 | pages = 359–66 | date = April 1995 | pmid = 7714789 }}</ref> |
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It has been shown to produce useful ],<ref name="pmid15943758">{{cite journal |vauthors=Gallantine EL, Meert TF |date=July 2005 |title=A comparison of the antinociceptive and adverse effects of the mu-opioid agonist morphine and the delta-opioid agonist SNC80 |journal=Basic & Clinical Pharmacology & Toxicology |volume=97 |issue=1 |pages=39–51 |doi=10.1111/j.1742-7843.2005.pto_97107.x |pmid=15943758}}</ref> ]<ref name="pmid16163520">{{cite journal | vauthors = Jutkiewicz EM, Rice KC, Traynor JR, Woods JH | title = Separation of the convulsions and antidepressant-like effects produced by the delta-opioid agonist SNC80 in rats | journal = Psychopharmacology | volume = 182 | issue = 4 | pages = 588–96 | date = November 2005 | pmid = 16163520 | pmc = 1307499 | doi = 10.1007/s00213-005-0138-9 }}</ref> and ] effects in animal studies,<ref name="pmid16491101">{{cite journal | vauthors = Perrine SA, Hoshaw BA, Unterwald EM | title = Delta opioid receptor ligands modulate anxiety-like behaviors in the rat | journal = British Journal of Pharmacology | volume = 147 | issue = 8 | pages = 864–72 | date = April 2006 | pmid = 16491101 | pmc = 1760715 | doi = 10.1038/sj.bjp.0706686 }}</ref><ref name="pmid15272214">{{cite journal | vauthors = Saitoh A, Kimura Y, Suzuki T, Kawai K, Nagase H, Kamei J | title = Potential anxiolytic and antidepressant-like activities of SNC80, a selective delta-opioid agonist, in behavioral models in rodents | journal = Journal of Pharmacological Sciences | volume = 95 | issue = 3 | pages = 374–80 | date = July 2004 | pmid = 15272214 | doi = 10.1254/jphs.FPJ04014X | doi-access = free }}</ref> but its usefulness is limited by producing ] at high doses,<ref name="pmid17112570">{{cite journal | vauthors = Danielsson I, Gasior M, Stevenson GW, Folk JE, Rice KC, Negus SS | title = Electroencephalographic and convulsant effects of the delta opioid agonist SNC80 in rhesus monkeys | journal = Pharmacology, Biochemistry, and Behavior | volume = 85 | issue = 2 | pages = 428–34 | date = October 2006 | pmid = 17112570 | pmc = 1820742 | doi = 10.1016/j.pbb.2006.09.012 }}</ref> and so SNC-80 is not used medically, although it is a useful compound in scientific research. |
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== References == |
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{{Reflist|35em}} |
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{{Opioidergics}} |
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{{analgesic-stub}} |