2773. Cyproheptadine

Nomenclature

CAS number: 129-03-3
4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine; 1-methyl-4-(5H-dibenzo[a,d]cycloheptenylidene)piperidine; 5-(1-methylpiperidylidene-4)-5H-dibenzo[a,d]cycloheptene; 1-methyl-4-(5-dibenzo[a,e]cycloheptatrienylidene)piperidine.
C21H21N; mol wt 287.40.
C 87.76%, H 7.36%, N 4.87%.

Description and references

Serotonin and histamine antagonist. Prepn: E. L. Engelhardt, US 3014911 (1961 to Merck & Co.); E. L. Engelhardt et al., J. Med. Chem. 8, 829 (1965). Improved prepn: M. M. Cid et al., Tetrahedron 44, 6197 (1988). Metabolism: C. C. Porter et al., Drug Metab. Dispos. 3, 189 (1975). HPLC determn in serum and plasma: E. A. Novak et al., J. Chromatogr. 339, 457 (1985). Toxicity study: J. J. Loux et al., Arzneim.-Forsch. 28, 1644 (1978). Comprehensive description: H. Y. Aboul-Enein, A. A. Al-Badr, Anal. Profiles Drug Subs. 9, 155-179 (1980). Clinical trial as an appetite stimulant in cystic fibrosis: D. N. Homnick et al., Pediatr. Pulmonol. 40, 251 (2005).

Chemical structure

Properties

Crystals from dil ethanol, mp 112.3-113.3°.

Derivative

Hydrochloride sesquihydrate.

Nomenclature

CAS number: 41354-29-4
Periactin (Merck & Co.); Periactine (Merck & Co.); Peritol (Medphano).
C21H22ClN.1 1/2 H2O; mol wt 332.87.
C 75.77%, H 6.96%, Cl 10.65%, N 4.21%, O 2.40%.

Properties

Crystals from abs ethanol + ether, dec 252.6-253.6°. uv max (0.1N H2SO4): 224, 285 nm (E1%1cm 1656, 355). 1.0 g is sol in 1.5 ml methanol, 16 ml chloroform, 35 ml alc, 275 ml H2O. Practically insol in ether. LD50 orally in mice: 74.2 mg/kg (Loux).

Derivative

Hydrochloride monohydrate.

Nomenclature

CAS number: 6032-06-0

Properties

Crystals, mp 214-216°. Soly in water: ≈5 mg/ml.

Therapeutic Category

Antihistaminic; antipruritic; appetite stimulant.

Therapeutic Category (Veterinary)

Antihistaminic; antipruritic; appetite stimulant.

Keywords

Antihistaminic; Tricyclics; Other Tricyclics; Antipruritic