| Identification | More | [Name]
Cyclobenzaprine hydrochloride | [CAS]
6202-23-9 | [Synonyms]
5-[3-DIMETHYLAMINOPROPYLIDENE]-DIBENZO[A,E]CYCLOHEPTATRIENE HYDROCHLORIDE
AMITRITYLINE HYDROCHLORIDE IMP B
CYCLOBENZAPRINE HCL
CYCLOBENZAPRINE HYDROCHLORIDE
3-(5h-dibenzo(a,d)cyclohepten-5-ylidene)-n,n-dimethyl-1-propanaminhydroc
5-(3-dimethylaminopropylidene)-5h-dibenzo-(a,d)cycloheptenehydrochloride
d)cycloheptene-delta(sup5)-gamma-propylamine,n,n-dimethyl-5h-dibenzo(hydr
flexeril
flexiban
n,n-dimethyl-5h-dibenzo(a,d)cycloheptene-delta(sup5,gamma)-propylaminehydro
proheptatrienmonohydrochloride
3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl(dimethyl)ammonium chloride
3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine Hydrochloride
Flexiba
1-Propanamine, 3-(5H-dibenzoa,dcyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride
CYCLOBENZAPRINEHYDROCHLORIDE,USP
Lisseril
Proheptatriene hydrochloride | [EINECS(EC#)]
228-264-4 | [Molecular Formula]
C20H22ClN | [MDL Number]
MFCD00079039 | [Molecular Weight]
311.85 | [MOL File]
6202-23-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
216-2180C | [Fp ]
9℃ | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
≥15.59 mg/mL in DMSO; ≥5.32 mg/mL in EtOH; ≥54.3 mg/mL in H2O | [Water Solubility ]
Completely soluble in water | [form ]
neat | [color ]
White to Almost white | [Usage]
Use as muscle relaxant (skeletal) | [λmax]
290nm(lit.) | [Merck ]
14,2713 | [InChIKey]
VXEAYBOGHINOKW-UHFFFAOYSA-N | [CAS DataBase Reference]
6202-23-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
HP0875000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29214990 | [Toxicity]
LD50 in mice (mg/kg): 35 i.v., 250 orally (Metysova) |
| Hazard Information | Back Directory | [Description]
Cyclobenzaprine is a skeletal muscle relaxant that also has sedative properties.1,2,3 It has been shown to antagonize muscarinic receptors (Kis = 25, 60, and 6 nM for M1, M2, and M3, respectively), serotonin 5-HT2 receptors (Kis = 56 and 330 nM for 5-HT2C and 5-HT2B, respectively), and histamine H1 receptor (IC50 = 20 nM).4,5,6 | [Chemical Properties]
Crystalline Solid | [Originator]
Flexeril,Merck Sharp andDohme,US,1977 | [Uses]
Cyclobenzaprine hydrochloride has been used to study its effect on the muscles of dystrophin-deficient mdx5Cv mice. | [Uses]
Cyclobenzaprine hydrochloride cam be used as muscle relaxant (skeletal).
| [Uses]
Cyclobenzaprine hydrochloride can be used as a serotonin receptor inhibitor.
| [Definition]
ChEBI: The hydrochloride salt of cyclobenzaprine. A centrally acting skeletal muscle relaxant, it is used 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 | [General Description]
Cyclobenzaprine is a tricyclic agent, which has anti-depressant and anti-cholinergic properties. It lowers the tonic somatic motor activity of motor neuron systems. Cyclobenzaprine prevents the uptake of?noradrenaline. It is used to treat neck,?back and myofascial pain. Cyclobenzaprine functions as a nerve impulse inhibitor. | [References]
[1]. honda m, nishida t, ono h. tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-ht2 receptors. european journal of pharmacology, 2003, 458(1): 91-99.
[2]. barnes c d, fung s j, gintautas j. brainstem noradrenergic system depression by cyclobenzaprine. neuropharmacology, 1980, 19(2): 221-224.
[3]. leysen j e. 5-ht2 receptors. current drug targets-cns & neurological disorders, 2004, 3(1): 11-26. |
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