Profadol

Not to be confused with propanol, propofol, or propranolol.

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]

Profadol

Clinical data
ATC code	none
Legal status
Legal status	US: Analogue to a Schedule I/II drug (Analogue of Tapentadol, Schedule II)
Identifiers
IUPAC name 3-(1-methyl-3-propyl-pyrrolidin-3-yl)phenol
CAS Number	428-37-5
PubChem CID	9882
ChemSpider	9498
UNII	41GDG43FTT
ChEMBL	ChEMBL161204
CompTox Dashboard (EPA)	DTXSID30861924
Chemical and physical data
Formula	C14H21NO
Molar mass	219.328 g·mol−1

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

• Bromadol
• C-8813
• Ciramadol
• Faxeladol
• Prodilidine
• Tapentadol
• Tramadol