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

color 

White to Almost white

λmax

290nm(lit.)

Merck 

14,2713

InChIKey

VXEAYBOGHINOKW-UHFFFAOYSA-N

CAS DataBase Reference

6202-23-9(CAS DataBase Reference)

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

• Language:English Provider:SigmaAldrich

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 (K_is = 25, 60, and 6 nM for M₁, M₂, and M₃, respectively), serotonin 5-HT₂ receptors (K_is = 56 and 330 nM for 5-HT_2C and 5-HT_2B, 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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