Sercloremine

Sercloremine (CGP-4718A), usually as the hydrochloride salt, is a drug which was developed in the 1980s and was formerly under investigation as an antidepressant, but was never marketed.[1][2] It acts as a selective, reversible inhibitor of monoamine oxidase A (RIMA) and serotonin reuptake inhibitor.[1][3]

Sercloremine
Names
Preferred IUPAC name
4-(5-Chloro-1-benzofuran-2-yl)-1-methylpiperidine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C14H16ClNO/c1-16-6-4-10(5-7-16)14-9-11-8-12(15)2-3-13(11)17-14/h2-3,8-10H,4-7H2,1H3
    Key: FTKTZRKAVSDSRA-UHFFFAOYSA-N
SMILES
  • CN1CCC(CC1)C2=CC3=C(O2)C=CC(=C3)Cl
Properties
Chemical formula
 C14H16ClNO
Molar mass 249.74 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis
Patents:[4][5]

Ex 12: The ether formation between 5-chlorosalicylaldehyde [635-93-8] (1) and 4-(chloromethyl)-pyridine HCl [1822-51-1] (2) gives 2-[(4-pyridyl)-methoxy]-5-chlorobenzaldehyde CID:16769957 (3). Heating of this intermediate gives 4-(5-chloro-2-benzofuranyl)-pyridine CID:23312193 (4). Alkylation with methyl iodide leads to 1-methyl-4-(5-chloro-2-benzofuranyl)-pyridinium iodide, CID:23312242 (5). The reduction with sodium borohydride completes the synthesis of Sercloremine (6).

References
  1. Luttinger D, Hlasta DJ (January 1987). "Antidepressant agents". In Hesp B, Bailey DM (eds.). Annual Reports in Medicinal Chemistry. Vol. 22. Academic Press. pp. 21–30 (25). ISBN 978-0-08-058366-2.
  2. Ganellin CR, Triggle DJ (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1801–. ISBN 978-0-412-46630-4.
  3. Delini-Stula A, Fischbach R, Gnirss F, Bures E, Pöldinger W (1985). "Early experience with CGP 4718 A (Sercloremine), a new selective and reversible MAO-A and 5-HT-uptake inhibitor, in the treatment of depressive patients". Drug Development Research. 6 (4): 371–384. doi:10.1002/ddr.430060409. ISSN 0272-4391. S2CID 85113482.
  4. DE2408476 idem Karl Schenker, Raymond Bernasconi, U.S. Patent 4,210,655 (1980 to Ciba-Geigy Corporation).
  5. Karl Schenker & Raymond Bernasconi, U.S. Patent 4,600,719 (1986 to Novartis Corp).


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