| Revision as of 03:10, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox← Previous edit |
Latest revision as of 22:49, 4 April 2023 edit undoEntranced98 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers172,984 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper |
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{{Short description|Chemical compound}} |
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{{drugbox |
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{{Drugbox |
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| verifiedrevid = 443987359 |
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| IUPAC_name = 1-Pyridin-4-yl-''N''-(pyridin-4-ylmethyl)methanamine |
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| image = Gapicomine.png |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = off market (was used in EU countries) |
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| routes_of_administration = ] (tablet) |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 68955 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = WWW0P95393 |
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| UNII = WWW0P95393 |
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| CAS_number = 1539-39-5 |
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| verifiedrevid = 443483663 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| IUPAC_name = 1-Pyridin-4-yl-''N''-(pyridin-4-ylmethyl)methanamine |
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| ChEMBL = 2103958 |
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| image = Gapicomine.png |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| CAS_number = 1539-39-5 |
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| ChemSpiderID = 62178 |
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| ATC_prefix = none |
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| smiles = n1ccc(cc1)CNCc2ccncc2 |
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| ATC_suffix = |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| PubChem = 68955 |
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| StdInChI = 1S/C12H13N3/c1-5-13-6-2-11(1)9-15-10-12-3-7-14-8-4-12/h1-8,15H,9-10H2 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| DrugBank = |
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| StdInChIKey = AUQQZPGNRKTPSQ-UHFFFAOYSA-N |
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| C=12|H=13|N=3 |
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<!--Chemical data--> |
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| molecular_weight = 199.25 g/mol |
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| C=12 | H=13 | N=3 |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = off market (was used in EU countries) |
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| routes_of_administration = oral (tablet) |
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}} |
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}} |
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'''Gapicomine''' (]) is a ] ]. It has been withdrawn from the market in the countries it was used in.<ref>{{cite web |url=http://www.justscience.de/en/drugbase/indexnominum/monograph.html?tx_crondavindexnominum_pi%5Bmonograph_uid%5D=3597&cHash=e51fae0af1 |title=Gapicomine Monograph, The Index Nominum |accessdate=2008-03-31 |format= |work=}}</ref> |
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'''Gapicomine''' (]) is a ] ]. It has been withdrawn from the market in the countries it was used in.<ref>{{cite web |url=http://www.justscience.de/en/drugbase/indexnominum/monograph.html?tx_crondavindexnominum_pi%5Bmonograph_uid%5D=3597&cHash=e51fae0af1 |title=Gapicomine Monograph, The Index Nominum |access-date=2008-03-31 }}</ref> |
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Also, gapicomine is a major component in the drug ].<ref>{{cite web |url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=211061 |title=Bicordin, PubChem |accessdate=2008-03-31 |format= |work=}}</ref> |
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Also, gapicomine is a major component in the drug ].<ref>{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=211061 |title=Bicordin, PubChem |access-date=2008-03-31 }}</ref> |
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==History== |
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==History== |
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Gapicomine was discovered in 1970 by ] ] ]. It was first published about in an article of ''The Polish Journal of Medicine and Pharmacy'' describing the derivative drug ] in 1974.<ref name="PMID4453155">{{cite journal |author=Samochowiec L, Wójcicki J, Gregorczyk K, Szmatloch E. |title=Bicordin--a new drug in the treatment of coronary heart disease. |journal=Mater Med Pol. |volume= 6|issue= 4|pages=298–300 |year=1974 |pmid=4453155 |doi=}}</ref> |
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Gapicomine was discovered in 1970 by ] ] ]. It was first published about in an article of ''The Polish Journal of Medicine and Pharmacy'' describing the derivative drug ] in 1974.<ref name="PMID4453155">{{cite journal |vauthors=Samochowiec L, Wójcicki J, Gregorczyk K, Szmatloch E |title=Bicordin--a new drug in the treatment of coronary heart disease. |journal=Mater Med Pol. |volume= 6|issue= 4|pages=298–300 |year=1974 |pmid=4453155 }}</ref> |
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==Synthesis== |
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] |
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The oxime formation between isonicotinaldehyde ('''1''') and hydroxylamine gives 4-Pyridinealdoxime ('''2'''). This is then reduced by catalytic hydrogenation over Raney-Nickel into 4-Picolylamine ('''3'''). Reductive amination of the last with a second equivalent of isonicotinaldehyde affords gapicomine ('''4'''). |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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{{Vasodilators used in cardiac diseases}} |
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{{Vasodilators used in cardiac diseases}} |
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] |
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] |
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] |
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] |
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{{cardiovascular-drug-stub}} |
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{{cardiovascular-drug-stub}} |
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] |
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