Hexylcaine hydrochloride, also called cyclaine ( Merck) or osmocaine, is a short-acting

local anesthetic A local anesthetic (LA) is a medication that causes absence of pain sensation. In the context of surgery, a local anesthetic creates an absence of pain in a specific location of the body without a loss of consciousness, as opposed to a general a ...

. It acts by inhibiting

sodium channel Sodium channels are integral membrane proteins that form ion channels, conducting sodium ions (Na+) through a cell's membrane. They belong to the superfamily of cation channels and can be classified according to the trigger that opens the chan ...

conduction. Overdose can lead to

headache Headache is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of depression in those with severe headaches. Headaches can occur as a result ...

tinnitus Tinnitus is the perception of sound when no corresponding external sound is present. Nearly everyone experiences a faint "normal tinnitus" in a completely quiet room; but it is of concern only if it is bothersome, interferes with normal hearin ...

, numbness and tingling around the mouth and tongue,

convulsion A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is sometimes used as a ...

s, inability to breathe, and decreased heart function.

Synthesis

The

reductive amination Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is considered ...

between

1-Amino-2-propanol 1-Aminopropan-2-ol is the organic compound with the formula CH3CH(OH)CH2NH2. It is an amino alcohol. The term ''isopropanolamine'' may also refer more generally to the additional homologs diisopropanolamine (DIPA) and triisopropanolamine (TIPA). ...

8-96-6(1) and

cyclohexanone Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohex ...

gives 1-Cyclohexylamino-2-propanol 03-00-4(2). Treatment with benzoyl chloride gives the ester, completing the synthesis of Hexylcaine (3).

References

Local anesthetics Benzoate esters Cyclohexylamines {{nervous-system-drug-stub