Cyclobenzaprine

Base Information

• Chemical Name: Cyclobenzaprine
• CAS No.: 303-53-7
• Molecular Formula: C20H21 N
• Molecular Weight: 275.393
• Hs Code.: 2921499090
• European Community (EC) Number: 206-145-8
• UNII: 69O5WQQ5TI
• DSSTox Substance ID: DTXSID0046933
• Nikkaji Number: J5.490I
• Wikipedia: Cyclobenzaprine
• Wikidata: Q5198674
• NCI Thesaurus Code: C28947
• RXCUI: 21949
• Pharos Ligand ID: V5Y6J1T72VV9
• Metabolomics Workbench ID: 43191
• ChEMBL ID: CHEMBL669
• Mol file: 303-53-7.mol

Synonyms:cyclobenzaprine;cyclobenzaprine hydrochloride;Flexeril;Lisseril

Chemical Property of Cyclobenzaprine

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 7.65E-11mmHg at 25°C
• Refractive Index: 1.7500 (estimate)
• Boiling Point: 405.9 °C at 760 mmHg
• PKA: pKa 8.47 (Uncertain)
• Flash Point: 177.8 °C
• PSA: 3.24000
• Density: 1.096 g/cm³
• LogP: 5.35580
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 275.167399674
• Heavy Atom Count: 21
• Complexity: 365

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclobenzaprine(1.0mg/mLinMethanol) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC=C1C2=CC=CC=C2C=CC3=CC=CC=C31
• Recent ClinicalTrials: Fixed-dose Combination of Etoricoxib + Cyclobenzaprine for Pain Relief After Third Molar Extraction in Brazil
• Recent EU Clinical Trials: A SINGLE BLIND, SINGLE DOSE STUDY OF THE SEDATIVE EFFECTS OF THIOCOLCHICOSIDE, TIZANIDINE AND CYCLOBENZAPRINE IN HEALTHY MALE, HUMAN VOLUNTEERS
• Description: Cyclobenzaprine is structurally similar to tricyclic antidepressants. It acts at the brain stem level.
• Uses: Relaxant (muscle). 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.
• Therapeutic Function: Muscle relaxant

Technology Process of Cyclobenzaprine

There total 6 articles about Cyclobenzaprine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

cyclobenzaprine N-oxide (6682-26-4) → Cyclobenzaprine (303-53-7)

Guidance literature:

With sodium tetrahydroborate; In water; at 50 - 60 ℃; chemoselective reaction;

DOI:10.1016/j.tetlet.2010.08.045

Reference yield:

5-[3-(N,N-dimethylamino)propyl]-5H-dibenzo[a,d]cyclohepten-5-ol (18029-54-4) → Cyclobenzaprine (303-53-7)

Guidance literature:

With acetic anhydride; Heating;

DOI:10.1021/jo01048a057

Reference yield:

3-(Dimethylamino)propyl chloride (109-54-6) → Cyclobenzaprine (303-53-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) Mg, (ii) /BRN= 743171/, THF

2: Ac₂O / Heating

With acetic anhydride;

DOI:10.1021/jo01048a057

upstream raw materials:

3-(Dimethylamino)propyl chloride

dibenzosuberenon

5-[3-(N,N-dimethylamino)propyl]-5H-dibenzo[a,d]cyclohepten-5-ol

cyclobenzaprine N-oxide

Downstream raw materials:

ethyl N-<3-(5H-dibenzocyclohepten-5-ylidene)propyl>-N-methylcarbamate

cyclobenzaprine N-oxide

5-[3-(methylamino)propylidene]-5H-dibenzo[a,d]cycloheptene

Refernces