| 词条 | JWH-007 |
| 释义 |
| verifiedrevid = 451554740 | IUPAC_name = 1-pentyl-2-methyl-3-(1-naphthoyl)indole | image = JWH-007.svg | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = Schedule II | legal_UK = | legal_US = | legal_DE = Anlage II | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 155471-10-6 | ATC_prefix = | ATC_suffix = | PubChem = 10360860 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID = 8536309 | C=25 | H=25 | N=1 | O=1 | molecular_weight = 355.471 g/mol | smiles = c14ccccc4cccc1C(=O)c3c2ccccc2n(c3C)CCCCC | StdInChI = 1S/C25H25NO/c1-3-4-9-17-26-18(2)24(22-14-7-8-16-23(22)26)25(27)21-15-10-12-19-11-5-6-13-20(19)21/h5-8,10-16H,3-4,9,17H2,1-2H3 | StdInChIKey = IBBNKINXTRKICJ-UHFFFAOYSA-N }}JWH-007 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It was the most active of the first group of N-alkyl naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially described with the discovery of the N-morpholinylethyl compounds pravadoline (WIN 48,098), WIN 55,225 (JWH-200) and WIN 55,212-2 by the Sterling Winthrop group.[1] Several other N-alkyl substituents were found to be active by Huffman's team including the n-butyl, n-hexyl, 2-heptyl and cyclohexylethyl groups,[2] but it was subsequently determined that the 2-methyl group on the indole ring is not required for CB1 binding, and tends to increase affinity for CB2 instead.[3][4] Consequently, the 2-desmethyl derivative of JWH-007, JWH-018 has slightly higher binding affinity for CB1, with an optimum binding of 9.00nM at CB1 and 2.94nM at CB2, and JWH-007 displayed optimum binding of 9.50nM at CB1 and 2.94nM at CB2.[5] Another drug similarly named JHW-007 (not JWH) is a cocaine analogue (the di-para-fluoro benztropine, being essentially a hybrid between benzatropine & difluoropine; with fluorine groups in the former or being descarbmethoxy in the latter) and atypical dopamine reuptake inhibitor,[6] but is distinct from and not the same as this JWH-007.[7] LawJWH-007 was banned in Sweden on 1 October 2010 as a hazardous good harmful to health, after being identified as an ingredient in "herbal" synthetic cannabis products.[8][9] JWH-007 is illegal in Poland since 08.06.2010 on the basis of 'Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii' published in Dz.U. 2011 nr 105 poz. 614[10] As of October 2015 JWH-007 is a controlled substance in China.[11] See also
References1. ^{{Cite journal |pmid= 1335057 |year= 1992 |author= Compton, D. R.|title= Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol |volume= 263 |issue= 3 |pages= 1118–1126 |journal= The Journal of Pharmacology and Experimental Therapeutics |display-authors=etal}} {{Cannabinoids}}{{Cannabinoidergics}}{{cannabinoid-stub}}2. ^{{cite journal | last1 = Huffman | first1 = JW | last2 = Dong | first2 = D | year = 1994 | title = Design, Synthesis and Pharmacology of Cannabimimetic Indoles | url = | journal = Bioorganic & Medicinal Chemistry Letters | volume = 4 | issue = 4| pages = 563–566 | doi=10.1016/s0960-894x(01)80155-4}} 3. ^{{Cite journal |doi= 10.1016/j.bmc.2004.09.050 |pmid= 15582455 |year= 2005 |last= Huffman |first= J.|title= Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists. |volume= 13 |issue= 1 |pages= 89–112 |journal= Bioorganic & Medicinal Chemistry |display-authors=etal}} 4. ^{{Cite journal | pmid = 15974991 | year = 2005 | last1 = Huffman | first1 = J. W. | last2 = Padgett | first2 = L. W. | title = Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes | volume = 12 | issue = 12 | pages = 1395–1411 | journal = Current Medicinal Chemistry | doi = 10.2174/0929867054020864}} 5. ^{{Cite journal |pmid= 10940540 |year= 2000 |author= Aung, M. M.|title= Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding |volume= 60 |issue= 2 |pages= 133–140 |journal= Drug and Alcohol Dependence |doi= 10.1016/S0376-8716(99)00152-0 |display-authors=etal}} 6. ^{{cite journal|last1=Rothman|first1=Richard B.|last2=Baumann|first2=Michael H.|last3=Prisinzano|first3=Thomas E.|last4=Newman|first4=Amy Hauck|title=Dopamine transport inhibitors based on GBR12909 and benztropine as potential medications to treat cocaine addiction|journal=Biochemical Pharmacology|volume=75|issue=1|year=2008|pages=2–16|issn=0006-2952|doi=10.1016/j.bcp.2007.08.007|pmid=17897630|pmc=2225585}} 7. ^{{cite journal|last1=Velázquez-Sánchez|first1=Clara|last2=García-Verdugo|first2=José M.|last3=Murga|first3=Juan|last4=Canales|first4=Juan J.|title=The atypical dopamine transport inhibitor, JHW 007, prevents amphetamine-induced sensitization and synaptic reorganization within the nucleus accumbens|journal=Progress in Neuro-Psychopharmacology and Biological Psychiatry|volume=44|year=2013|pages=73–80|issn=0278-5846|doi=10.1016/j.pnpbp.2013.01.016|pmid=23385166}} 8. ^Swedish Code of Statutes Regulation (2010:1086). 9. ^Swedish Code of Statutes Regulation (2010:1086). (pdf) 10. ^{{cite web|title=Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )|url=http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614|publisher=ISAP|accessdate=12 June 2011}} 11. ^{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}} 3 : Designer drugs|JWH cannabinoids|Naphthoylindoles |
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