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| Routes of administration | Oral |
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| Formula | C17H27N |
| Molar mass | 245.410 g·mol−1 |
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Gamfexine (WIN-1,344) is a centrally actingstimulantdrug, which was tested as an adjunct treatment for withdrawn patients withschizophrenia, but while effective for treating withdrawal it made psychotic symptoms worse.[1]
It was stated that gamfexine was the progenitor in the discovery ofvenlafaxine.[2] This could be the reason why both agents share the samesuffix.
The precursor chemical is made frombenzyl cyanide andbromocyclohexane.[3] This compound serves dual use in the synthesis ofdrofenine,hexasonium &feclemine.
The synthesis of gamfexine has been discussed:[4][5] Patents:[6][7] The method discussed by Lednicer & Mitscher is slightly different from the patented procedure and uses 2-Cyclohexylidene-2-phenylacetonitrile [10461-98-0].[8] This chemical is an odoriferous substance. It is known to have been used in the synthesis ofFenclexonium.
Alkylation ofcyclohexylphenylacetonitrile [3893-23-0] (1) with 2-chloroethyldimethylamine (2), using NaNH2 as base, gives nitrile,PC412902 (3). Removal of the nitrile group apparently occurred upon reaction with more NaNH2. This completed the synthesis ofGamfexine (4).
N.B. Note that the removal of cyanide also occurs in one of the syntheses ofchlorpheniramine. Here though,sulfuric acid was used as the reagent for this step.
An alternative synthesis strategy is envisioned to consist of Mannich reaction & organometallic addition to the carbonyl group (c.f.trihexyphenidyl), followed by reductive removal of the tertiary hydroxyl group; or by starting form Benzoylcyclohexane [712-50-5].
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