Alinidine

Title: Alinidine
CAS Registry Number: 33178-86-8
CAS Name: N-(2,6-Dichlorophenyl)-4,5-dihydro-N-2-propenyl-1H-imidazol-2-amine
Additional Names: 2-(N-allyl-2,6-dichloroanilino)-2-imidazoline; 2-[N-allyl-N-(2,6-dichlorophenyl)amino]-2-imidazoline
Manufacturers' Codes: ST-567
Molecular Formula: C12H13Cl2N3
Molecular Weight: 270.16
Percent Composition: C 53.35%, H 4.85%, Cl 26.25%, N 15.55%
Literature References: Specific bradycardic agent; analog of clonidine, q.v. Prepn: H. Stähle et al., DE 1958201; eidem, US 3708485 (1971, 1973 both to Boehringer, Ing.); eidem, J. Med. Chem. 23, 1217 (1980). Clinical pharmacology: D. W. G. Harron et al., J. Cardiovasc. Pharmacol. 4, 213 (1982). Mode of action study: J. S. Millar, E. M. Vaughan Williams, Lancet 1, 1291 (1981). HPLC determn in human plasma: U.-W. Wiegand et al., J. Chromatogr. 223, 238 (1981). Clinical pharmacokinetics: eidem, J. Cardiovasc. Pharmacol. 4, 59 (1982). Hemodynamic effects in angina or infarction: M. L. Simoons, P. G. Hugenholtz, Eur. Heart J. 5, 227 (1984). Review of pharmacology and potential therapeutic uses: D. W. G. Harron, R. G. Shanks, ibid. 6, 722-729 (1985).
Properties: Crystals, mp 130-131° (Stähle, 1973); also reported as mp 127-129° (Stähle, 1980). pKa 10.42.
Melting point: mp 130-131° (Stähle, 1973); mp 127-129° (Stähle, 1980)
pKa: pKa 10.42
Derivative Type: Hydrobromide
Molecular Formula: C12H14BrCl2N3
Molecular Weight: 351.07
Percent Composition: C 41.05%, H 4.02%, Br 22.76%, Cl 20.20%, N 11.97%
Properties: Crystals from methanol + water, mp 193-194°.
Melting point: mp 193-194°
Aliskiren Alitretinoin Alizapride Alizarin Alizarin Cyanine Green F

Alinidine
Alinidine.png
Systematic (IUPAC) name
N-(2,6-dichlorophenyl)-N-(prop-2-en-1-yl)-4,5-dihydro-1H-imidazol-2-amine
Clinical data
Legal status Uncontrolled
Identifiers
CAS number 33178-86-8 N
ATC code None
PubChem CID 36354
ChemSpider 33429 YesY
UNII E7IDJ8DS1D YesY
ChEMBL CHEMBL278581 YesY
Chemical data
Formula C12H13Cl2N3 
Mol. mass 270.16 g/mol
 N (what is this?)  (verify)

Alinidine (ST567) is a negative chronotrope that was developed in the 1970s and 1980s. It causes bradycardia by inhibiting the pacemaker current by altering the maximal channel conductance and alter the voltage threshold.[1] The development of alinidine was halted because it was not sufficiently specific for its target. It also has a blocking effect on calcium channels and potassium channels. It also causes elongation of re-polarisation after an action potential.[2]

Alinidine did not improve outcomes among patients with acute myocardial infarction in a randomized controlled trial.[3]