Profadol
{{Short description|Chemical compound}}
{{Distinguish | propanol | propofol | propranolol}}
{{Drugbox
| 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 = {{fdacite|correct|FDA}}
| 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.{{cite patent | country = DE | number = 1303096 }} 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.{{cite book | vauthors = Schröder E, Rufer C, Schmiechen R |title=Arzneimittelchemie 1. Grundlagen, Nerven, Muskeln und Gewebe |date=1976 |location=Stuttgart | publisher = Georg Thieme Verlag |isbn=3-13-520601-7}}
Synthesis
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, [https://pubchem.ncbi.nlm.nih.gov/compound/164137621 CID:164137621] (3). Imide formation occurs upon treatment with methylamine giving 3-(3-Methoxyphenyl)-1-methyl-3-propylpyrrolidine-2,5-dione, [https://pubchem.ncbi.nlm.nih.gov/compound/163444474 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
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