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| Formula | C19H25NO2 |
| Molar mass | 299.414 g·mol−1 |
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Proxorphan (INN), also known asproxorphan tartate (USAN) (developmental code nameBL-5572M), is anopioidanalgesic andantitussivedrug of themorphinan family that was never marketed.[1] It acts preferentially as aκ-opioid receptorpartial agonist and to a lesser extent as aμ-opioid receptor partial agonist.[2][3][4][5][6]
Starting material for this preparation is ketoester1, available by one of the classical benzomorphan syntheses.[7] Condensation with theylide fromTriethyl phosphonoacetate (HWE reaction) affords diester2.Catalytic hydrogenation proceeds from the less hindered face to afford the corresponding saturated diester (3). The esters are then reduced by means ofLiAlH4 to give theglycol (4); this undergoes internal ether formation on treatment with acid to form thepyran ring of5.Von Braun reaction withBrCN (orethyl chloroformate) followed bysaponification of the intermediate leads to the 2° amine (6). This is converted to the cyclopropylmethyl derivative8 by acylation withcyclopropylcarbonyl chloride[8][9] followed by reduction of the thus formed amide (7) with LiAlH4. Cleaving off the O-methyl ether with sodiumethanethiol affords proxorphan (9).
