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Cyclobenzaprine hydrochloride

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Cyclobenzaprine hydrochloride Basic information

Product Name:
Cyclobenzaprine hydrochloride
Synonyms:
  • 3-(5h-dibenzo(a,d)cyclohepten-5-ylidene)-n,n-dimethyl-1-propanaminhydroc
  • 5-(3-dimethylaminopropylidene)-5h-dibenzo-(a,d)cycloheptenehydrochloride
  • CYCLOBENZAPRINEHYDROCHLORIDE,USP
  • Lisseril
  • Proheptatriene hydrochloride
  • Cyclobenzaprine hydrochloride,5-(3-Dimethylaminopropylidene)dibenzo[a,e]cycloheptatriene hydrochloride
  • Cyclobenzaprine Hydrochloride (200 mg)
  • 3-(5H-Dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine hydrochloride
CAS:
6202-23-9
MF:
C20H22ClN
MW:
311.85
EINECS:
228-264-4
Product Categories:
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Heterocyclic Compounds
  • FLEXERIL
Mol File:
6202-23-9.mol
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Cyclobenzaprine hydrochloride Chemical Properties

Melting point:
216-2180C
Flash point:
9℃
storage temp. 
Inert atmosphere,Room Temperature
Water Solubility 
Completely soluble in water
solubility 
≥15.59 mg/mL in DMSO; ≥5.32 mg/mL in EtOH; ≥54.3 mg/mL in H2O
form 
Solid
color 
White to Almost white
λmax
290nm(lit.)
Merck 
14,2713
InChIKey
VXEAYBOGHINOKW-UHFFFAOYSA-N
CAS DataBase Reference
6202-23-9(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn,T,F
Risk Statements 
20/21/22-39/23/24/25-23/24/25-11
Safety Statements 
36-45-36/37-16-7
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)

MSDS

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Cyclobenzaprine hydrochloride Usage And Synthesis

Description

Cyclobenzaprine is a skeletal muscle relaxant that also has sedative properties. 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).

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 can be used as a serotonin receptor inhibitor.

Uses

Cyclobenzaprine hydrochloride cam be used as muscle relaxant (skeletal).

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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