13-09597. Tolonidine [Archived]

Nomenclature

CAS number: 4201-22-3
N-(2-Chloro-4-methylphenyl)-4,5-dihydro-1H-imidazol-2-amine; 2-(2-chloro-p-toluidino)-2-imidazoline; 2-(2-chloro-4-methylphenyl)amino-1,3-diazacyclopentene-2.
C10H12ClN3; mol wt 209.68.
C 57.28%, H 5.77%, Cl 16.91%, N 20.04%.

Description and references

Orally active antihypertensive agent, related structurally to clonidine. Prepn: NL 6411516; US 3236857; US 6411516; US 3454701 (1965, 1966, 1969 all to Boehringer, Ing.). Synthesis and hypotensive activity: P. B. M. Timmermans et al., Rec. Trav. Chim. 97, 51 (1978). Pharmacological properties: C. Cosnier et al., Arzneim.-Forsch. 25, 1557, 1802, 1926 (1975). Structure-activity study: P. B. M. Timmermans, P.A. Van Zwieten, J. Med. Chem. 20, 1636 (1977). Chromatographic study: P. B. M. Timmermans et al., J. Chromatogr. 144, 215 (1977). Quantum chemical studies: eidem, Arzneim.-Forsch. 27, 2266 (1977). Radioimmunoassay disposition study: B. Jarrott, S. Spector, J. Pharmacol. Exp. Ther. 207, 195 (1978). Toxicity study: D. Cosnier et al., Arzneim.-Forsch. 25, 1926 (1975).

Chemical structure

Properties

Crystals from benzene/petr ether, mp 148-150°. pKa 9.41.

Derivative

Nitrate.

Nomenclature

CAS number: 57524-15-9
CERM-10137; Euctan (Synthelabo).
C10H12ClN3.HNO3; mol wt 272.69.
C 44.05%, H 4.81%, Cl 13.00%, N 20.55%, O 17.60%.

Properties

Crystals, mp 162-164°. LD50 in male mice, rats (mg/kg): 160, 420 orally; 21.25, 42 i.v. (Cosnier).

Therapeutic Category

Antihypertensive.

Keywords

Antihypertensive; Imidazole Derivatives

Status

This monograph has been retired and is no longer subject to revision or update.