isobucaine
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = [2-methyl-2-(2-methylpropylamino)propyl] benzoate
| image = Isobucaine.svg
| tradename =
| pregnancy_category =
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 14055-89-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2XV8GIV746
| ATC_prefix =
| ATC_suffix =
| PubChem = 26427
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 24619
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL =
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG =
| C=15 | H=23 | N=1 | O=2
| smiles = CC(C)CNC(C)(C)COC(=O)c1ccccc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C15H23NO2/c1-12(2)10-16-15(3,4)11-18-14(17)13-8-6-5-7-9-13/h5-9,12,16H,10-11H2,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YGSFZBYOMFZJPV-UHFFFAOYSA-N
}}
Isobucaine is a local anesthetic.{{cite book | vauthors = Thoma KH | title = Accepted Dental Remedies | publisher = American Dental Association | location= Chicago | edition = 26th | date = 1961 | page = 30 }}
Synthesis
The reductive amination between aminomethyl propanol (1) and isobutanal [78-84-2] (2) afforded N-Isobutyl-1,1-dimethyl-2-hydroxyethanamine, [https://pubchem.ncbi.nlm.nih.gov/compound/18315986 CID:18315986] (3). Acylation of the amine with benzoyl chloride [98-88-4] hypothetically goes initially to the amide (4'). The acid catalysis used in the reaction leads to an N to O acyl migration to afford isobucaine (5).
See also
References
{{reflist}}
{{Local anesthetics}}
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