Fluprazine

Fluprazine (DU-27,716) is a drug of the phenylpiperazine class. It is a so-called serenic or antiaggressive agent.[1] It is closely related to several other piperazines, including eltoprazine and batoprazine, and TFMPP, as well as more distantly to the azapirones such as buspirone. The pharmacology of fluprazine is unknown, but it is likely to act as an agonist at the 5-HT1A and 5-HT1B receptors like its sister compound eltoprazine.

Fluprazine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • 2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethylurea
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H19F3N4O
Molar mass316.328 g·mol−1
3D model (JSmol)
SMILES
  • C1CN(CCN1CCNC(=O)N)C2=CC=CC(=C2)C(F)(F)F

Synthesis

Note that the last step of the synthesis for adding the urea was exemplified primarily for carbamazepine.

Patent:[2] Prec (Ex XXVII):[3]

The alkylation between Trifluoromethylphenylpiperazine [15532-75-9] (1) and chloroacetonitrile (2) gives 2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}acetonitrile [76716-94-4] (3). The reduction of the nitrile with lithium aluminium hydride gives 2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethanamine [27144-85-0] (4). The reaction with potassium cyanate in aqueous mineral acid gives the urea and hence completed the synthesis of Fluprazine (5).

See also
  • Phenylpiperazine

References
  1. van der Poel AM, Olivier B, Mos J, Kruk MR, Meelis W, van Aken JH (1982). "Anti-aggressive effect of a new phenylpiperazine compound (DU27716) on hypothalamically induced behavioural activities". Pharmacol Biochem Behav. 17 (1): 147–153. doi:10.1016/0091-3057(82)90277-5. PMID 6889746. S2CID 34142798.
  2. Hans Heinz Haeck, Feddo Cornelius Hillen, EP 0015615 (1983 to Duphar International Research B.V).
  3. Edgar S Schipper & Paul Levitan, U.S. Patent 3,574,839 (1971 to Shulton Inc).
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