Profadol

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Chemical compound

title: "Profadol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["3-hydroxyphenyl-compounds", "pyrrolidines", "drugs-developed-by-parke-davis"] description: "Chemical compound" topic_path: "general/3-hydroxyphenyl-compounds" source: "https://en.wikipedia.org/wiki/Profadol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| IUPAC_name = 3-(1-methyl-3-propyl-pyrrolidin-3-yl)phenol | image = Profadol skeletal.svg | image_class = skin-invert-image | width = 200px

| tradename = | pregnancy_category = | legal_US = analogue | legal_US_comment = (Analogue of Tapentadol, Schedule II) | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number = 428-37-5 | ATC_prefix = none | ATC_suffix = | PubChem = 9882 | DrugBank = | ChEMBL = 161204 | ChemSpiderID = 9498 | UNII_Ref = | UNII = 41GDG43FTT

| C=14 | H=21 | N=1 | O=1

Profadol (CI-572) is an opioid analgesic which was developed in the 1960s by Parke-Davis. It acts as a mixed agonist-antagonist of the μ-opioid receptor. The analgetic potency is about the same as of pethidine (meperidine), the antagonistic effect is 1/50 of nalorphine.

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/c/c8/Profadol_synthesis.svg" caption="3149123}} (1964 to Parke Davis and Co LLC)."] ::

The Knoevenagel condensation between 3'-Methoxybutyrophenone [21550-06-1] and Ethyl cyanoacetate gives (1). Conjugate addition of cyanide gives (2). Hydrolysis of both nitrile groups, saponification of the ester and decarboxylation gives the diacid, CID:164137621 (3). Imide formation occurs upon treatment with methylamine giving 3-(3-Methoxyphenyl)-1-methyl-3-propylpyrrolidine-2,5-dione, CID:163444474 (4). Reduction of the imide by lithium aluminium hydride gave [1505-32-4][29369-01-5] (5). Demethylation completed the synthesis of Profadol (6).

References

References

  1. {{cite patent
  2. (1976). "Arzneimittelchemie 1. Grundlagen, Nerven, Muskeln und Gewebe". Georg Thieme Verlag.
  3. Cavalla, J. F.; Jones, R.; Welford, M.; Wax, J.; Winder, C. V. (1964). "Analgetics Based on the Pyrrolidine Ring. III". Journal of Medicinal Chemistry. 7 (4): 412–415. doi:10.1021/jm00334a005.
  4. John Frederick Cavalla & Alan Chapman White, {{Cite patent. DE. 1272296 (1968 to Parke Davis and Co LLC).
  5. Cavalla John Frederick, {{US patent. 3149123 (1964 to Parke Davis and Co LLC).

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3-hydroxyphenyl-compoundspyrrolidinesdrugs-developed-by-parke-davis