Description
Cyclobenzaprine is structurally similar to tricyclic antidepressants. It acts at the brain stem
level.
Originator
Flexeril,Merck Sharp andDohme,US,1977
Uses
It is used as an adjuvant agent for relieving muscle spasms associated with severe
diseased conditions of the muscle. A synonym of this drug is flexeril.
Definition
ChEBI: 5-Methylidene-5H-dibenzo[a,d]cycloheptene in which one of the hydrogens of the methylidene group is substituted by a 2-(dimethylamino)ethyl group. A centrally acting skeletal muscle relaxant, it is used as its h
drochloride salt in the symptomatic treatment of painful muscle spasm.
Manufacturing Process
In an initial step, dibenzo [a,d]cyclohepten-5-one is reacted with the Grignardreagent of 3-dimethylaminopropyl chloride and hydrolyzed to give 5-(3-dimethylaminopropyl)-dibenzo[a,d][1,4]cycloheptatriene-5-ol. Then 13 g ofthat material, 40 ml of hydrochloric acid, and 135 ml of glacial acetic acid isrefluxed for 3 hours. The solution is then evaporated to dryness in vacuoand added to ice water which is then rendered basic by addition of ammoniumhydroxide solution. Extraction of the basic solution with chloroform andremoval of the solvent from the dried chloroform extracts yields the crudeproduct which when distilled in vacuo yields essentially pure 5-(3-dimethylaminopropylidene)-dibenzo[a,d][1,4]cycloheptatriene, BP 173°C to177°C at 1.0 mm.
brand name
Flexeril
(McNeil).
Therapeutic Function
Muscle relaxant
Synthesis
Cyclobenzaprine, N,N-dimethyl-3-(dibenzo[a,d]cyclohepten-5-ylidene)
propylamine (15.3.9), is synthesized by reacting 5H-dibenzo[a,d]cyclohepten-5-one with
3-dimethylaminopropylmagnesium chloride and subsequent dehydration of the resulting
carbinol (15.3.8) in acidic conditions into cyclobenzaprine (15.3.9).
