303-53-7 Usage
Description
Cyclobenzaprine HCL, also known by its brand name Flexeril, is a centrally acting skeletal muscle relaxant that is structurally similar to tricyclic antidepressants. It acts at the brain stem level and is used in the symptomatic treatment of painful muscle spasm. The chemical definition of Cyclobenzaprine HCL is 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.
Uses
Used in Pharmaceutical Industry:
Cyclobenzaprine HCL is used as a muscle relaxant for the treatment of painful muscle spasms. It works by blocking nerve impulses that cause muscle contractions, providing relief from muscle pain and stiffness.
Used as an Adjuvant Agent:
Cyclobenzaprine HCL is used as an adjuvant agent for relieving muscle spasms associated with severe diseased conditions of the muscle. It helps to alleviate the discomfort and pain caused by muscle spasms, improving the patient's quality of life.
Originator
Flexeril,Merck Sharp andDohme,US,1977
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.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 303-53-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 3 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 303-53:
(5*3)+(4*0)+(3*3)+(2*5)+(1*3)=37
37 % 10 = 7
So 303-53-7 is a valid CAS Registry Number.
InChI:InChI=1/C20H21N.ClH/c1-21(2)13-7-11-19-15-17-9-4-3-8-16(17)14-18-10-5-6-12-20(18)19;/h3-6,8-12,14-15H,7,13H2,1-2H3;1H/b19-11-;
303-53-7Relevant articles and documents
A chemoselective deoxygenation of N-oxides by sodium borohydride-Raney nickel in water
Gowda, Narendra B.,Rao, Gopal Krishna,Ramakrishna, Ramesha A.
experimental part, p. 5690 - 5693 (2010/11/05)
A simple and convenient protocol for deoxygenation of aliphatic and aromatic N-oxides to the corresponding amines in good to excellent yield using sodium borohydride-Raney nickel in water is reported. Other functional moieties such as alkenes, halides, ethers, and amides are unaffected under the present reaction condition.