83846-83-7 Usage
Description
Ketanserin is a potent antagonist of the serotonin (5-HT) receptor that is selective for 5-HT2 (IC50 = 6.3 nM; Ki = 2.1 nM). It has no activity at 5-HT1 receptors but does have activity at histamine type 1, α1-adrenergic, and dopamine receptors with Ki values of 10, 10, and 220 nM, respectively. Ketanserin induces dose-dependent inhibition of contractile responses to 5-HT in isolated rat caudal artery, canine basilar, carotid, coronary and gastrosplenic arteries, and canine gastrosplenic and saphenous veins. Ketanserin (10 mg/kg/day) significantly decreases blood pressure (BP), blood pressure variability (BPV), and hypertensive organ damage in spontaneously hypertensive rats. Formulations containing ketanserin have been used to treat hypertension in early-onset preeclampsia.
Uses
Selective 5-HT2A serotonin receptor antagonist
Biological Activity
Selective 5-HT 2A serotonin receptor antagonist; can also be used to discriminate between 5-HT 1D and 5-HT 1B receptor subtypes.
Biochem/physiol Actions
Selective 5-HT2 serotonin receptor antagonist. Ketanserin significantly reduces nicotine self-administration in rats, supporting an unexpected involvement of serotonin in nicotine addiction.
Check Digit Verification of cas no
The CAS Registry Mumber 83846-83-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,3,8,4 and 6 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 83846-83:
(7*8)+(6*3)+(5*8)+(4*4)+(3*6)+(2*8)+(1*3)=167
167 % 10 = 7
So 83846-83-7 is a valid CAS Registry Number.
InChI:InChI=1/C22H22FN3O3.C4H6O6/c23-17-7-5-15(6-8-17)20(27)16-9-11-25(12-10-16)13-14-26-21(28)18-3-1-2-4-19(18)24-22(26)29;5-1(3(7)8)2(6)4(9)10/h1-8,16H,9-14H2,(H,24,29);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2+
83846-83-7Relevant articles and documents
Reinvestigation of the synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) via 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione (2) or dihydro-5H-oxazole(2,3-b)quinazolin-5-one (1)
Fakhraian, Hossein,Heydary, Mehdi
, p. 151 - 156 (2014/02/14)
The synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) using respectively equimolar amounts of 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione (2) with 4-(parafluorobenzoyl)piperidine (3) and dihydro-5H-oxazole(2,3-b) quinazolin-5-one (1) with hydrochloride salt of 4-(parafluorobenzoyl)piperidine (3.HCl) is reinvestigated. The one-pot reaction of ethyl-2-aminobenzoate with ethyl chloroformate and ethanol amine has afforded 3-(2-chloroethyl)-2,4-(1H,3H) -quinazolinedione (2) (86%) that was then refluxed with 4-(parafluorobenzoyl) piperidine (3) in ethyl methyl ketone in the presence of sodium carbonate to obtain free base of ketanserin (87%). In another attempt, a very pure hydrochloride salt of ketanserin (5.HCl) was synthesized using equimolar amounts of dihydro-5H-oxazole(2,3-b)quinazolin-5-one (1) and hydrochloride salt of 4-(parafluorobenzoyl)piperidine (3.HCl) by a solvent-less fusion method. Thus, under optimized conditions, 180°C and a reaction time of 30 min, the powder mixture was transformed into glassy crystals that were initially readily soluble in chloroform but were transformed afterwards over time (2 h) to white precipitates (5.HCl) suspended in chloroform with a yield of 72%.
