Hexylcaine

{{short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 461769300

| IUPAC_name = 1-cyclohexylaminopropan-2-yl benzoate

| image = Hexylcaine Structure.svg

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life = <10 minutes

| IUPHAR_ligand = 7196

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 532-77-4

| ATC_prefix = None

| ATC_suffix =

| ATC_supplemental =

| PubChem = 10770

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00473

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10315

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 511IU0826Z

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C14172

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1197

| C=16 | H=23 | N=1 | O=2

| smiles = O=C(OC(CNC1CCCCC1)C)c2ccccc2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DKLKMKYDWHYZTD-UHFFFAOYSA-N

}}

Hexylcaine hydrochloride, also called cyclaine (Merck) or osmocaine, is a short-acting local anesthetic. It acts by inhibiting sodium channel conduction. Overdose can lead to headache, tinnitus, numbness and tingling around the mouth and tongue, convulsions, inability to breathe, and decreased heart function.{{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 = }}

Synthesis

File:Hexylcaine synthesis.svg

The reductive amination between 1-Amino-2-propanol [78-96-6] (1) and cyclohexanone gives 1-Cyclohexylamino-2-propanol [103-00-4] (2). Treatment with benzoyl chloride gives the ester, completing the synthesis of Hexylcaine (3).{{Citation needed|date=November 2023}}

References

{{Reflist}}

{{Local anesthetics}}

Category:Local anesthetics

Category:Benzoate esters

Category:Cyclohexylamines

{{nervous-system-drug-stub}}