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Mu-opioid receptor agonists
Conorfone
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    Conorfone

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    Conorfone
    Conorfone2DCSD.svg
    Clinical data
    ATC code
    • None
    Identifiers
    • (5α,8β)-17-(Cyclopropylmethyl)-8-ethyl-3-methoxy-4,5-epoxymorphinan-6-one
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    Chemical and physical data
    Formula C23H29NO3
    Molar mass 367.489 g·mol−1
    3D model (JSmol)
    • O=C4[C@@H]5Oc1c2c(ccc1OC)CC3N(CC[C@]25[C@H]3[C@@H](CC)C4)CC6CC6

    Conorfone (INN; TR-5109), also known as conorphone and codorphone, as well as conorphone hydrochloride (USAN), is an opioid analgesic that was never marketed. It is an analogue of hydrocodone substituted with an 8-ethyl group and an N-cyclopropylmethyl group. It acts as a mixed agonist-antagonist at the μ-opioid receptor, and is slightly more potent than codeine in analgesic effects but associated with somewhat greater side effects.

    Synthesis

    Codorphone synthesis:

    Exposure of thebaine (1) to mild acid leads to hydrolysis of the enol ether function followed by migration of the double bond to yield the conjugated enone (2). Addition of lithium diethylcuprate proceeds by 1,4-addition from the less hindered side to give the intermediate 3. Treatment of that with cyanogen bromide under von Braun reaction conditions leads to the isolable aminocyanide. This is the converted to the secondary amine (4) by treatment with aqueous base. Alkylation of that intermediate with cyclopropylmethyl chloride affords the analgesic codorphone (5).

    See also



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