Butanilicaine
{{chembox
| ImageFile=Butanilicaine.svg
| ImageSize=
| IUPACName=N2-Butyl-N1-(2-chloro-6-methylphenyl)glycinamide
| SystematicName=2-(Butylamino)-N-(2-chloro-6-methylphenyl)acetamide
| OtherNames=
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7X3WV51F4N
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 55518
| PubChem=22379
| SMILES=CCCCNCC(=O)NC1=C(C=CC=C1Cl)C
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 3785-21-5
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 2104238
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21004
| InChI = 1/C13H19ClN2O/c1-3-4-8-15-9-12(17)16-13-10(2)6-5-7-11(13)14/h5-7,15H,3-4,8-9H2,1-2H3,(H,16,17)
| InChIKey = VWYQKFLLGRBICZ-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H19ClN2O/c1-3-4-8-15-9-12(17)16-13-10(2)6-5-7-11(13)14/h5-7,15H,3-4,8-9H2,1-2H3,(H,16,17)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VWYQKFLLGRBICZ-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula=C13H19ClN2O
| MolarMass=254.75576
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = N01
| ATCCode_suffix = BB05
}}
|Section7={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
Butanilicaine is a local anesthetic. It is also known by the name Hostacaine.
Synthesis
Amide formation by the combination of 2-chloro-6-methylaniline (1) and chloroacetyl chloride (2) gives the intermediate (3), which is used to alkylate N-butylamine (4) to yield butanilicaine.{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0155 |title=Butanilicaine |publisher=Thieme |access-date=2024-07-01 }}{{cite journal |doi=10.1021/ja01541a028 |title=N-(Substituted Aminoacyl)-chloroanilines |date=1958 |last1=Epstein |first1=Elias |last2=Kaminsky |first2=Daniel |journal=Journal of the American Chemical Society |volume=80 |issue=8 |pages=1892–1895 }}{{Cite patent|GB|782971}} 1957 to Hoechst AG.
References
{{Reflist|2}}
{{Local anesthetics}}
{{nervous-system-drug-stub}}