167144-79-8 Usage
Description
(3R,5R)-5-[2-[2-[2-(3-METHOXYPHENYL)ETHYL]PHENOXY]ETHYL]-1-METHYL-3-PYRROLIDINOL HYDROCHLORIDE, also known as R-96544 Hydrochloride, is a complex organic compound with a unique chemical structure. It is the active form of a novel 5-HT2A receptor antagonist, R-102444, which plays a significant role in various biological processes.
Uses
Used in Pharmaceutical Industry:
R-96544 Hydrochloride is used as a 5-HT2A receptor antagonist for inhibiting platelet aggregation induced by serotonin (5-hydroxytryptamine, 5-HT). This application is particularly relevant in the treatment of conditions related to blood clotting and vascular health.
Used in Research Applications:
In addition to its pharmaceutical applications, R-96544 Hydrochloride is also utilized in research settings to study the role of 5-HT2A receptors in various physiological and pathological processes. This helps in understanding the underlying mechanisms of diseases and developing targeted therapeutic strategies.
Biological Activity
Potent, selective 5-HT 2 receptor antagonist; displays some selectivity for 5-HT 2A receptors (K i = 1.6 nM). IC 50 values are 2.2, 310, 2400, 3700, > 5000 and > 5000 nM for 5-HT 2 , a 1 -adrenergic, D 2 dopamine, 5-HT 1 , 5-HT 3 and b-adrenergic receptors respectively. Inhibits 5-HT-induced platelet aggregation and pressor responses in vivo .
Check Digit Verification of cas no
The CAS Registry Mumber 167144-79-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,7,1,4 and 4 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 167144-79:
(8*1)+(7*6)+(6*7)+(5*1)+(4*4)+(3*4)+(2*7)+(1*9)=148
148 % 10 = 8
So 167144-79-8 is a valid CAS Registry Number.
InChI:InChI=1/C22H29NO3.ClH/c1-23-16-20(24)15-19(23)12-13-26-22-9-4-3-7-18(22)11-10-17-6-5-8-21(14-17)25-2;/h3-9,14,19-20,24H,10-13,15-16H2,1-2H3;1H/t19-,20-;/m1./s1
167144-79-8Relevant articles and documents
[2-(O-Phenylalkyl)phenoxy]alkylamines III: Synthesis and selective serotonin-2 receptor binding (2).
Tanaka,Goto,Ito,Hayakawa,Sugidachi,Ogawa,Asai,Fujimoto
, p. 1729 - 1739 (2007/10/03)
A series of 12-(2-phenylethyl)phenoxy]ethylpyrrolidine derivatives were synthesized, and their affinity for serotonin-2 (5-HT2) and dopamine-2 (D2) receptors was examined. Among them, compound 17, (2R,4R)-4-hydroxy-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxylethyl] -1-methylpyrrolidine hydrochloride, showed high 5-HT2 receptor affinity in vitro. This compound was a more potent inhibitor of ex vivo 5-HT-induced platelet aggregation than compound 3, which was previously shown to be more potent than ketanserin (1) and sarpogrelate (2a). However, compound 17 produced gastric irritation in rats. Therefore, we carried out a further derivatization of 17, and compound 45 (R-102444), a lauryl ester prodrug of compound 17, was found to be a promising candidate as an antithrombotic agent. Oral administration of R-102444 produced a marked inhibition of 5-HT-induced ex vivo platelet aggregation, and R-102444 did not cause any gastric irritation. The antiaggregatory effects of R-102444 were more potent than those of sarpogrelate (2a) and its active metabolite, M-1 (2b). In addition, R-102444 exhibited more potent antithrombotic effects than sarpogrelate in a rat photochemically-induced thrombosis model.
ALPHA-OMEGA-DIARYLALKANE COMPOUNDS SEROTONIN-2 RECEPTOR AGONISTS
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, (2008/06/13)
Compounds of formula (I): STR1 [wherein: R 1 is aryl; R 2 is hydrogen, alkyl, alkoxy, halogen or cyano; R 3 is a group of formula--B--NR 4 R 5, where R 4 and R 5 are independently hydrogen, alkyl or substituted alkyl or R 4 and R 5, together with the nitr