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Pharmacology stubs
PRE-084
Другие языки:

    PRE-084

    Подписчиков: 0, рейтинг: 0
    PRE-084
    PRE-084 SVG file.svg
    Clinical data
    ATC code
    • none
    Identifiers
    • 2-morpholin-4-ylethyl 1-phenylcyclohexane-1-carboxylate
    CAS Number
    PubChem CID
    IUPHAR/BPS
    ChemSpider
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C19H27NO3
    Molar mass 317.429 g·mol−1
    3D model (JSmol)
    • c1ccccc1C2(CCCCC2)C(=O)OCCN3CCOCC3
    • InChI=1S/C19H27NO3/c21-18(23-16-13-20-11-14-22-15-12-20)19(9-5-2-6-10-19)17-7-3-1-4-8-17/h1,3-4,7-8H,2,5-6,9-16H2 ☒N
    • Key:RQHKZUBCUZVZEF-UHFFFAOYSA-N ☒N
     ☒NcheckY (what is this?)  (verify)

    PRE-084 is a sigma receptor agonist, selective for the σ1 subtype. It has nootropic and antidepressant actions in animal studies, as well as antitussive and reinforcing effects. PRE-084 increases the expression of GDNF.

    Synthesis

    Patent:

    Sodium hydride mediated alkylation between Benzyl cyanide (1) and 1,5-dibromopentane [111-24-0] (2) gives 1-phenylcyclohexanecarbonitrile [2201-23-2] (3). Hydrolysis of the nitrile by treatment with aqueous potassium hydroxide in DEG gives 1-phenylcyclohexanecarboxylic acid [1135-67-7] (4). Halogenation with thionyl chloride gives 1-phenylcyclohexanecarbonyl chloride [2890-42-8]. This intermediate was not isolated but reacted with 2-morpholinoethanol [622-40-2] (5) to give the ester and hence, completing the synthesis of PRE084 (6).



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