2713. Cyclobenzaprine

Nomenclature

CAS number: 303-53-7
3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine; N,N-dimethyl-5H-dibenzo[a,d]cyclohepten-Δ5,γ-propylamine; 5-(3-dimethylaminopropylidene)dibenzo[a,e]cycloheptatriene; 1-(3-dimethylaminopropylidene)-2,3:6,7-dibenzo-4-suberene; proheptatriene; MK-130; Ro-4-1577; RP-9715.
C20H21N; mol wt 275.39.
C 87.23%, H 7.69%, N 5.09%.

Description and references

Prepn: GB 858187 (1961 to Hoffmann-La Roche); Villani et al., J. Med. Pharm. Chem. 5, 373 (1962); Winthrop et al., J. Org. Chem. 27, 230 (1962). Pharmacology: C. D. Barnes, W. L. Adams, Neuropharmacology 17, 445 (1978); N. N. Share, ibid. 721; and toxicology: J. Metysova et al., Arch. Int. Pharmacodyn. Ther. 144, 481 (1963). Metabolism: G. Belvedere et al., Biomed. Mass Spectrom. 1, 329 (1974); H. B. Hucker et al., Drug Metab. Dispos. 6, 184 (1978). Bioavailability: eidem, J. Clin. Pharmacol. 17, 719 (1977). Clinical studies: J. V. Basmajian, Arch. Phys. Med. Rehabil. 5, 58 (1978); B. R. Brown, J. Womble, J. Am. Med. Assoc. 240, 1151 (1978). Comprehensive description: M. L. Cotton, G. R. B. Down, Anal. Profiles Drug Subs. 17, 41-72 (1988).

Chemical structure

Properties

bp1 175-180°. uv max: 224, 289 nm (log ε 4.57, 4.02), (Villani et al.)

Derivative

Hydrochloride.

Nomenclature

CAS number: 6202-23-9
Flexeril (Merck & Co.); Flexiban (Merck & Co.).
C20H21N.HCl; mol wt 311.85.
C 77.03%, H 7.11%, N 4.49%, Cl 11.37%.

Description and references

Use as muscle relaxant: N. N. Share, FR 2100873 (1972 to Frosst), C.A. 78, 47801n (1973).

Properties

Crystals from isopropanol, mp 216-218°. Soly in water: >20 g/100 ml. Freely sol in water, methanol, ethanol; sparingly sol in isopropanol; slightly sol in chloroform, methylene chloride. Practically insol in hydrocarbons. uv max: 226, 295 nm (ε 52300, 12000). LD50 in mice (mg/kg): 35 i.v., 250 orally (Metysova).

Therapeutic Category

Muscle relaxant (skeletal).

Keywords

Muscle Relaxant (Skeletal)