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Cinfenine

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Abandoned antidepressant

Pharmaceutical compound
Cinfenine
Clinical data
Drug classAntidepressant; Coronary vasodilator
Identifiers
IUPAC name
  • (E)-N-(2-benzhydryloxyethyl)-N-methyl-3-phenylprop-2-en-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H27NO
Molar mass357.497 g·mol
3D model (JSmol)
SMILES
  • CN(CCOC(C1=CC=CC=C1)C2=CC=CC=C2)C/C=C/C3=CC=CC=C3
InChI
  • InChI=1S/C25H27NO/c1-26(19-11-14-22-12-5-2-6-13-22)20-21-27-25(23-15-7-3-8-16-23)24-17-9-4-10-18-24/h2-18,25H,19-21H2,1H3/b14-11+
  • Key:QTKQVDXGCWKEHE-SDNWHVSQSA-N

Cinfenine (INNTooltip International Nonproprietary Name) is a drug described as an antidepressant and coronary vasodilator which was never marketed. It was first described in the literature by 1970. The drug is similar in chemical structure to the modafinil derivative and atypical dopamine reuptake inhibitor JJC8-016, as well as to the antihistamine and anticholinergic diphenhydramine and derivatives of diphenhydramine like ebastine. Other notable analogues acting as dopamine reuptake inhibitors have been synthesized as well.

See also

References

  1. ^ Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 278. ISBN 978-1-4757-2085-3. Retrieved 20 October 2024.
  2. Use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances (PDF). World Health Organization. 2024. p. 102. ISBN 978-92-4-009938-8.
  3. "CINFENINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS). Retrieved 20 October 2024.
  4. DE 1936206, "Diphenylmethoxyaethylaminoderivate und Verfahren zu ihrer Herstellung", published 22 January 1970, assigned to Koninklijke Pharmaceutische Fabrieken NV 
  5. "Cinfenine". PubChem. U.S. National Library of Medicine. Retrieved 20 October 2024.
  6. Hsin LW, Prisinzano T, Wilkerson CR, Dersch CM, Horel R, Jacobson AE, et al. (February 2003). "Synthesis and dopamine transporter affinity of chiral 1-ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents". Bioorg Med Chem Lett. 13 (3): 553–556. doi:10.1016/s0960-894x(02)00940-x. PMID 12565970.


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