| Revision as of 16:19, 23 February 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user← Previous edit |
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{{short description|Chemical compound}} |
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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 415527325 |
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| verifiedrevid = 461769300 |
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| IUPAC_name = 1-cyclohexylaminopropan-2-yl benzoate |
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| IUPAC_name = 1-cyclohexylaminopropan-2-yl benzoate |
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| image = Hexylcaine.PNG |
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| image = Hexylcaine Structure.svg |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_category = |
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| legal_status = |
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| routes_of_administration = |
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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 = <10 minutes |
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<!--Identifiers--> |
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| IUPHAR_ligand = 7196 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 532-77-4 |
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| ATC_prefix = None |
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| ATC_suffix = |
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| ATC_supplemental = |
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| PubChem = 10770 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00473 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10315 |
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| ChemSpiderID = 10315 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C14172 |
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| KEGG = C14172 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| InChI = 1/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3 |
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| ChEMBL = 1197 |
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<!--Chemical data--> |
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| C=16 | H=23 | N=1 | O=2 |
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| smiles = O=C(OC(CNC1CCCCC1)C)c2ccccc2 |
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| smiles = O=C(OC(CNC1CCCCC1)C)c2ccccc2 |
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| InChIKey = DKLKMKYDWHYZTD-UHFFFAOYAY |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3 |
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| StdInChI = 1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DKLKMKYDWHYZTD-UHFFFAOYSA-N |
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| StdInChIKey = DKLKMKYDWHYZTD-UHFFFAOYSA-N |
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| CAS_number = 532-77-4 |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1197 |
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| ATC_supplemental = |
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| PubChem = 10770 |
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| DrugBank = APRD01014 |
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| C = 16 | H = 23 | N = 1 | O = 2 |
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| molecular_weight = 261.359 g/mol |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = <10 minutes |
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| pregnancy_category = |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Hexylcaine hydrochloride''', also called '''cyclaine''' (]) or '''osmocaine''', is a short-acting ]. It acts by inhibiting ] conduction. Overdose can lead to ], ], ] around the mouth and tongue, ]s, ], and decreased heart function. |
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'''Hexylcaine hydrochloride''', also called '''cyclaine''' (]) or '''osmocaine''', is a short-acting ]. It acts by inhibiting ] conduction. Overdose can lead to ], ], ] around the mouth and tongue, ]s, ], and decreased heart function.<ref name="pmid13620024">{{cite journal | vauthors = Spellberg MA | title = Hexylcaine (cyclaine) as topical anesthetic in gastroscopy and esophagoscopy | journal = Gastroenterology | volume = 36 | issue = 1 | pages = 120–1 | date = January 1959 | pmid = 13620024 | doi = 10.1016/S0016-5085(59)80102-5| url = }}</ref> |
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==Synthesis== |
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] |
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The ] between ] ('''1''') and ] gives 1-Cyclohexylamino-2-propanol ('''2'''). Treatment with ] gives the ester, completing the synthesis of Hexylcaine ('''3''').{{Citation needed|date=November 2023}} |
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==References== |
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{{Reflist}} |
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{{Local anesthetics}} |
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{{Local anesthetics}} |
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{{nervous-system-drug-stub}} |
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{{nervous-system-drug-stub}} |