Profadol
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 3-(1-methyl-3-propyl-pyrrolidin-3-yl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC14H21NO
Molar mass219.328 g·mol−1

Profadol (CI-572) is an opioid analgesic which was developed in the 1960s by Parke-Davis.[1] 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.[2]

Synthesis

Synthesis:[3] Patents:[4][5]

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).

See also

References

  1. ↑ DE 1303096
  2. ↑ Schröder E, Rufer C, Schmiechen R (1976). Arzneimittelchemie 1. Grundlagen, Nerven, Muskeln und Gewebe. Stuttgart: Georg Thieme Verlag. ISBN 3-13-520601-7.
  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, DE 1272296 (1968 to Parke Davis and Co LLC).
  5. ↑ Cavalla John Frederick, U.S. Patent 3,149,123 (1964 to Parke Davis and Co LLC).
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