Gevotroline

Gevotroline

Gevotroline
Systematic (IUPAC) name
8-fluoro-2-[3-(pyridin-3-yl)propyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Identifiers
CAS number
ATC code None
PubChem
ChemSpider
UNII  YesY
Chemical data
Formula C19H20FN3 
Mol. mass 309.38 g/mol

Gevotroline (WY-47,384) is an atypical antipsychotic with a tricyclic structure which was under development for the treatment of schizophrenia by Wyeth-Ayerst.[1][2][3] It acts as a balanced, modest affinity D2 and 5-HT2 receptor antagonist and also possesses high affinity for the sigma receptor.[2][4][5][6] It was well-tolerated and showed efficacy in phase II clinical trials but was never marketed.[2][3]

Synthesis

Gevotroline synthesis:[7]

Lednicer drew it without the fluorine in his book. I simply copied what he did that is why no fluorine above.

See also

References

  1. ^ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC.  
  2. ^ a b c Bristol, James A. (1990). Annual Reports in Medicinal Chemistry (Volume 25). Boston: Academic Press.  
  3. ^ a b Stone, T. W.; Stone, Trevor (1996). CNS neurotransmitters and neuromodulators: dopamine. Boca Raton: CRC Press.  
  4. ^ Snyder SH, Largent BL (1989). "Receptor mechanisms in antipsychotic drug action: focus on sigma receptors". The Journal of Neuropsychiatry and Clinical Neurosciences 1 (1): 7–15.  
  5. ^ Matheson GK, Guthrie D, Bauer C, Knowles A, White G, Ruston C (January 1991). "Sigma receptor ligands alter concentrations of corticosterone in plasma in the rat". Neuropharmacology 30 (1): 79–87.  
  6. ^ Gudelsky GA, Nash JF (February 1992). "Neuroendocrinological and neurochemical effects of sigma ligands". Neuropharmacology 31 (2): 157–62.  
  7. ^ Abou-Gharbia, Magid; Patel, Usha R.; Webb, Michael B.; Moyer, John A.; Andree, Terrance H.; Muth, Eric A. (1987). "Antipsychotic activity of substituted .gamma.-carbolines". Journal of Medicinal Chemistry 30 (10): 1818–23.