Cinfenine

Cinfenine
Clinical data
Drug class	Antidepressant; Coronary vasodilator
Identifiers
	IUPAC name (E)-N-(2-benzhydryloxyethyl)-N-methyl-3-phenylprop-2-en-1-amine;
CAS Number	54141-87-6;
PubChem CID	6443800;
ChemSpider	4947762;
UNII	P26FL0O04P;
ChEMBL	ChEMBL2104102;
CompTox Dashboard (EPA)	DTXSID101023894 ;
Chemical and physical data
Formula	C25H27NO
Molar mass	357.497 g·mol−1
3D model (JSmol)	Interactive image;
	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.^[1]^[2]^[3] It was first described in the literature by 1970.^[1]^[4] 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.^[1]^[5] Other notable analogues acting as dopamine reuptake inhibitors have been synthesized as well.^[6]

References

^ ^a ^b ^c 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.
^ 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.
^ "CINFENINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS). Retrieved 20 October 2024.
^ DE 1936206, "Diphenylmethoxyaethylaminoderivate und Verfahren zu ihrer Herstellung", published 22 January 1970, assigned to Koninklijke Pharmaceutische Fabrieken NV
^ "Cinfenine". PubChem. U.S. National Library of Medicine. Retrieved 20 October 2024.
^ Hsin LW, Prisinzano T, Wilkerson CR, Dersch CM, Horel R, Jacobson AE, et al. (February 2003). "Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]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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