Hexylcaine

Chemical compound

None

Pharmacokinetic dataElimination half-life<10 minutesIdentifiers

IUPAC name

1-cyclohexylaminopropan-2-yl benzoate

CAS Number

532-77-4^Y

PubChem CID

10770

IUPHAR/BPS

7196

DrugBank

DB00473^Y

ChemSpider

10315^Y

UNII

511IU0826Z

KEGG

C14172^Y

ChEMBL

ChEMBL1197^Y

CompTox Dashboard (EPA)

DTXSID1047863

Chemical and physical dataFormulaC₁₆H₂₃NO₂Molar mass261.365 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C(OC(CNC1CCCCC1)C)c2ccccc2

InChI

InChI=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^Y
Key:DKLKMKYDWHYZTD-UHFFFAOYSA-N^Y

(verify)

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.^[1]

Synthesis

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]}

References

^ Spellberg MA (January 1959). "Hexylcaine (cyclaine) as topical anesthetic in gastroscopy and esophagoscopy". Gastroenterology. 36 (1): 120–1. doi:10.1016/S0016-5085(59)80102-5. PMID 13620024.
^ Cope, Arthur C.; Hancock, Evelyn M. (1944). "1-Alkylamino-2-propanols and their p-Nitro- and p-Aminobenzoates". Journal of the American Chemical Society 66 (9): 1453–1456. doi:10.1021/ja01237a010.
^ "Local Anesthetics". New England Journal of Medicine. 263 (19): 963–965.1960. doi:10.1056/NEJM196011102631912.
^ Cope Arthur C, U.S. patent 2,486,374 (1949 to Sharp & Dohme Inc).

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid

Aminobenzoic	Benzocaine Benzonatate Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine
Benzoic	Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine
ArCO2- (not para-amino or Ph)	Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane