7141. Pentylenetetrazole

Nomenclature

CAS number: 54-95-5
6,7,8,9-Tetrahydro-5H-tetrazolo[1,5-a]azepine; α,β-cyclopentamethylenetetrazole; 1,5-pentamethylenetetrazole; 6,7,8,9-tetrahydro-5-azepotetrazole; 1,2,3,3a-tetrazacyclohepta-8a,2-cyclopentadiene; 7,8,9,10-tetrazabicyclo[5.3.0]-8,10-decadiene; pentetrazol; Cardiazol (Knoll); Cenalene-M (Central Pharm.); Cenazol; Coranormol; Corazole; Corvasol (Rieswerke); Deumacard (Jenapharm); Gewazol; Korazol; Metrazol (Knoll); Phrenazol; Ventrazol.
C6H10N4; mol wt 138.17.
C 52.16%, H 7.29%, N 40.55%.

Description and references

Prepd by the addition of cyclohexanone to a benzene or Tetralin soln of hydrazoic acid: Schmidt, Ber. 57, 704 (1924); US 1564631 (1925); US 1599493 (1926); Prochazka, CS 92456 (1959), C.A. 56, 4776e (1962). Synthesis from caprolactam: Glushkov, Golovchinskaya, Zh. Prikl. Khim. 32, 920 (1959); Med. Prom. SSSR 14, no. 1, 12 (1960). Toxicity study: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).

Chemical structure

Properties

Slightly pungent, bitter crystals, mp 57-60°. Freely sol in water, most organic solvents. Aq solns are neutral to litmus. Very stable, not easily attacked by other substances. LD50 in rats (mg/kg): 85±2 s.c., 62 i.p. (Goldenthal).

Therapeutic Category

CNS stimulant.

Therapeutic Category (Veterinary)

CNS stimulant; narcotic antagonist.

Keywords

CNS Stimulant