Open Access Articles- Top Results for Piminodine


Systematic (IUPAC) name
ethyl 1-(3-anilinopropyl)-4-phenylpiperidine-4-carboxylate
Clinical data
13495-09-5 7pxY
PubChem CID 21950
ChemSpider 20628 7pxY
Chemical data
Formula C23H30N2O2
366.497 g/mol
 14pxY (what is this?)  (verify)

Piminodine (Alvodine) is an archaic opioid analgesic of the phenylpiperidine class, and is a structural analogue of pethidine (Meperidine/Demerol).[1] It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with hydroxyzine to intensify the effects. The duration of action is 2 to 4 hours and 7.5 to 10 mg via the subcutaneous route is the most common starting dose, being equal to 80 to 100 mg of pethidine, 40 to 60 mg of alphaprodine, and 10 mg of orally administered morphine.

Piminodine is equianalgesic to hydrocodone (but due to the non-cross-tolerance of morphinones at the mu-opioid receptor the conversion ratio is 2:1 from either to the other) but with a considerably shorter duration of action. Although piminodine has been demonstrated to serve as a prodrug to numerous active metabolism none of them are produced to a pharmacological relevant degree within the therapeutic dose range. Piminidone does however, present one major clinical advantage over pethidine and other the other phenylpiperdine derivatived opioids in that it does not produce the highly toxic norpethidine metabolite which has been associated with renal and hepatic degradation over long term use or short term severe binges, although pethidine is far less abusble.

Piminodine is said to provide an intense euphoria which is a quintessential departed from the typical opiate/opioid effects due to the additional targets of the drug: very minor sodium channel inhibition, antagonism of the Muscarinic Acetylcholine receptor (MAChR), action as a triple-reuptake-inhibitor (i.e. enhancing the levels of dopamine, serotonin, and norepinephrine), and agonism of the Delta opioid receptor and a very weak antagonism of the kappa opioid receptor. All these mechanisms are thought to contribute to piminodines analgesic effect but are all also associated with reducing anxiety and triggers a unique dirty-drug euphoria. Because of its high opioid potency, very rapid onset, and relatively short half-life it is very prone to abuse and diversion with the "rush" colloquially equated to that of the street drugs diamorphine (heroin) and dihydrodesoxymorphine (Krokodil). In the manner consistent with the benzenoid and phenylpiperadine drug classes and the codeine branch of the morphinans (i.e. tramadol and pethidine) piminidine can be combined with hydroxyzine to enhance the effect-per-dose multiplicatively.

Piminodine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening.[2][3]

Piminodine is currently a Schedule II controlled substance in the United States. It has a DEA ACSCN of 9730 and in 2013 the aggregate annual manufacturing quota for the US was zero. [4]


  1. Sim E, Dimoglo A, Shvets N, Ahsen V. Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics. Current Medicinal Chemistry. 2002 Aug;9(16):1537-45.
  2. Dekornfeld TJ, Lasagna L. The analgesic potency of piminodine (alvodine). Journal of Chronic Diseases. 1960 Aug;12:252-7.
  3. Woods LA, Deneau GA, Bennett DR, Domino EF, Seevers MH. A comparison of the pharmacology of two potent analgesic agents, piminodine (Win 14,098-2) and Win 13,797, with morphine and meperidine. Toxicology and Applied Pharmacology. 1961 May;3:358-79.


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