| Revision as of 13:07, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456700818 of page Rolziracetam for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 15:56, 4 July 2024 edit Boghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,723 edits consistent citation formatting |
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{{Short description|Chemical compound}} |
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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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{{cs1 config|mode=cs1|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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⚫ |
| verifiedrevid = 464383434 |
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| Watchedfields = changed |
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| ⚫ |
| verifiedrevid = 417962649 |
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| IUPAC_name = dihydro-1''H''-pyrrolizine-3,5(2''H'',6''H'')-dione |
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| IUPAC_name = dihydro-1''H''-pyrrolizine-3,5(2''H'',6''H'')-dione |
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| image = Rolziracetam structure.svg |
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| image = Rolziracetam structure.svg |
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| width = 78 |
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| width = 180 |
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| image2 = Rolziracetam3d.png |
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| image2 = Rolziracetam3d.png |
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| tradename = |
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| tradename = |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = S4 |
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| legal_status = Unscheduled (US) |
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| legal_US = Unscheduled |
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| routes_of_administration = Oral |
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| routes_of_administration = Oral |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 18356-28-0 --> |
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| CAS_number = 18356-28-0 |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| PubChem = 71893 |
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| PubChem = 71893 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 64906 |
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| ChemSpiderID = 64906 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = RES9I0LGG5 |
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| UNII = RES9I0LGG5 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=7 | H=9 | N=2 | O=2 |
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| C=7 | H=9 | N=2 | O=2 |
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| molecular_weight = 139.152 g/mol |
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| smiles = O=C2N1C(=O)CCC1CC2 |
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| smiles = O=C2N1C(=O)CCC1CC2 |
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| InChI = 1/C7H9NO2/c9-6-3-1-5-2-4-7(10)8(5)6/h5H,1-4H2 |
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| InChIKey = IEZDOKQWPWZVQF-UHFFFAOYAX |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C7H9NO2/c9-6-3-1-5-2-4-7(10)8(5)6/h5H,1-4H2 |
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| StdInChI = 1S/C7H9NO2/c9-6-3-1-5-2-4-7(10)8(5)6/h5H,1-4H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IEZDOKQWPWZVQF-UHFFFAOYSA-N |
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| StdInChIKey = IEZDOKQWPWZVQF-UHFFFAOYSA-N |
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| synonyms = <small>2,6,7,8-tetrahydro-1''H''-pyrrolizine-3,5-dione</small> |
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| synonyms = <small>2,6,7,8-tetrahydro-1''H''-pyrrolizine-3,5-dione</small>, CI 911 & Lukes-Šorm dilactam. |
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}} |
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}} |
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'''Rolziracetam''' is a ] drug of the ] family. |
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Rolziracetam was found to improve performance on a delayed-response task in aged rhesus monkeys. It has a wide margin of safety in animals and has been evaluated for use in cognitively impaired human subjects.<ref name="pmid3820221">{{cite journal | vauthors = Butler DE, Leonard JD, Caprathe BW, L'Italien YJ, Pavia MR, Hershenson FM, Poschel PH, Marriott JG | title = Amnesia-reversal activity of a series of cyclic imides | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 3 | pages = 498–503 | date = March 1987 | pmid = 3820221 | doi = 10.1021/jm00386a010 }}</ref> |
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==Synthesis== |
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:] |
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The ] group of ] (1) is reduced by palladium-catalysed ] to an ], which cyclises to give a mixture of the ] ester (2) and its corresponding acid (3). The mixture is ] using ] to convert all of the ester to the acid, and this material is cyclised to give rolziracetam using ].<ref>{{cite journal | vauthors = Leonard NJ, Hruda LR, Long FW | title = The synthesis of pyrrolizidines | journal = Journal of the American Chemical Society | volume = 69 | issue = 3 | pages = 690–692 | date = March 1947 | pmid = 20289459 | doi = 10.1021/ja01195a067 }}</ref><ref>{{cite patent |country=US |number=4663464 |inventor = Hoekstra MS |title=Process for the preparation of dihydro-1H-pyrrolizine-3,5-(2H,6H)-dione |status=patent |gdate=1987-05-05 |fdate=1986-03-21 |pridate=1986-03-21 |assign1=Warner Lambert Co LLC}}</ref> |
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==See also== |
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* ] |
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== References == |
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{{Reflist}} |
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{{Racetams}} |
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] |
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] |
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{{nervous-system-drug-stub}} |