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

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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}}

Category:Local anesthetics

Category:Acetanilides

Category:Chloroarenes

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