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| | CYCLOBENZAPRINE HCL Basic information |
| Product Name: | CYCLOBENZAPRINE HCL | | Synonyms: | CYCLOBENZAPRINE;CYCLOBENZAPRINE HCL;10,11-dehydroamitriptyline;1-Propanamine, 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-;3-(5h-dibenzo(a,d)cyclohepten-5-ylidene)-n,n-dimethyl-1-propanamin;3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine;5-(3-Dimetilaminopropiliden)-5H-dibenzo-(a,d)-ciclopentene;5H-Dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, N,N-dimethyl- | | CAS: | 303-53-7 | | MF: | C20H21N | | MW: | 275.39 | | EINECS: | 206-145-8 | | Product Categories: | | | Mol File: | 303-53-7.mol |  |
| | CYCLOBENZAPRINE HCL Chemical Properties |
| Boiling point | bp1 175-180° | | density | 0.9504 (rough estimate) | | refractive index | 1.7500 (estimate) | | pka | pKa 8.47 (Uncertain) | | BCS Class | 1 | | NIST Chemistry Reference | Cyclobenzaprine(303-53-7) |
| | CYCLOBENZAPRINE HCL Usage And Synthesis |
| Description | Cyclobenzaprine is structurally similar to tricyclic antidepressants. It acts at the brain stem
level. | | Originator | Flexeril,Merck Sharp andDohme,US,1977 | | Uses | Relaxant (muscle). | | 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). 
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| | CYCLOBENZAPRINE HCL Preparation Products And Raw materials |
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