Eucaine, also known as β-eucaine or Betacaine, is a drug that was previously used as a

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 an ...

. It was designed as an analog of

cocaine Cocaine (from , from , ultimately from Quechuan languages, Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly recreational drug use, used recreationally for its euphoria, euphoric effects. It is primarily obtained from t ...

and was one of the first synthetic chemical compounds to find general use as an anesthetic. It is a white, crystalline solid. Prior to World War I, Britain imported eucaine from Germany. During the war, a team including Jocelyn Field Thorpe and

Martha Annie Whiteley Martha Annie Whiteley, (11 November 1866 – 24 May 1956) was an English chemist and mathematician. She was instrumental in advocating for women's entry into the Chemical Society, and was best known for her dedication to advancing women's ...

developed a synthesis in Britain. The brand name Betacaine can sometimes refer to a preparation containing

lidocaine Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia. When used for local anaesthesia or in nerve blocks, lidoca ...

, not eucaine.

Synthesis

Condensation of diacetonamine 25-04-7(1) with

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...

(paraldehyde) rather than acetone gives the piperidone containing one less methyl group, i.e. 2,2,6-trimethylpiperidin-4-one 311-23-7(2). Reduction of the ketone with sodium amalgam gives the alcohol as a mixture of isomers, 2,2,6-trimethylpiperidin-4-ol (3). Benzoylation then affords beta-eucaine (4).

References

External links

* {{Wiktionary inline, eucaine Local anesthetics Piperidines Benzoate esters

Synthesis

See also

References

External links