Title: Tolonidine
CAS Registry Number: 4201-22-3
CAS Name: N-(2-Chloro-4-methylphenyl)-4,5-dihydro-1
H-imidazol-2-amine
Synonyms: 2-(2-chloro-
p-toluidino)-2-imidazoline; 2-(2-chloro-4-methylphenyl)amino-1,3-diazacyclopentene-2
Molecular Formula: C10H12ClN3
Molecular Weight: 209.68
Percent Composition: C 57.28%, H 5.77%, Cl 16.91%, N 20.04%
Literature 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).
Properties: Crystals from benzene/petr ether, mp 148-150°. pKa 9.41.
Melting point: mp 148-150°
pKa: pKa 9.41
Derivative Type: Nitrate
CAS Registry Number: 57524-15-9
Manufacturers' Codes: CERM-10137
Trademarks: Euctan (Synthelabo)
Molecular Formula: C10H12ClN3.HNO3
Molecular Weight: 272.69
Percent Composition: 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).
Melting point: mp 162-164°
Toxicity data: LD50 in male mice, rats (mg/kg): 160, 420 orally; 21.25, 42 i.v. (Cosnier)
Therap-Cat: Antihypertensive.
Keywords: Antihypertensive; Imidazole Derivatives.
Status: This monograph has been retired and is no longer subject to revision or update.