Glemanserin

Glemanserin (INN) (developmental code name MDL-11,939) is a drug which acts as a potent and selective 5-HT2A receptor antagonist.[1] The first truly selective 5-HT2A ligand to be discovered, glemanserin resulted in the development of the widely used and even more potent and selective 5-HT2A receptor antagonist volinanserin (MDL-100,907), which is a fluorinated analogue.[2] Though it was largely superseded in scientific research by volinanserin, glemanserin was investigated clinically for the treatment of generalized anxiety disorder.[3] However, it was ultimately found to be ineffective and was not marketed.[3]

Glemanserin
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • α-phenyl-1-(2-phenylethyl)-4-piperidine methanol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H25NO
Molar mass295.426 g·mol−1
3D model (JSmol)
SMILES
  • OC(c1ccccc1)C3CCN(CCc2ccccc2)CC3
InChI
  • InChI=1S/C20H25NO/c22-20(18-9-5-2-6-10-18)19-12-15-21(16-13-19)14-11-17-7-3-1-4-8-17/h1-10,19-20,22H,11-16H2
  • Key:AXNGJCOYCMDPQG-UHFFFAOYSA-N

Patented Use

Synthesis
Patents:[7][8]

The alkylation of 4-benzoylpiperidine [37586-22-4] (1) with 2-Phenylethylbromide [103-63-9] (2) gives (1-Phenethyl-piperidin-4-yl)-phenyl-methanone, CID:10379653 (3). The reduction of the carbonyl ketone to an alcohol with sopdium borohydride completed the synthesis of Glemanserin (4).

See also

References
  1. Mark W. Dudley; Norbert L. Wiech; Francis P. Miller; et al. (1988). "Pharmacological effects of MDL 11,939: A selective, centrally acting antagonist of 5-HT2 receptors". Drug Development Research. 13 (1): 29–43. doi:10.1002/ddr.430130104. S2CID 85075328.
  2. Berend Olivier (10 July 1997). Serotonin Receptors and Their Ligands. Elsevier. p. 167. ISBN 978-0-444-82041-9. Retrieved 6 May 2012.
  3. Sramek JJ, Robinson RE, Suri A, Cutler NR (February 1995). "Efficacy trial of the 5-HT2 antagonist MDL 11,939 in patients with generalized anxiety disorder". Journal of Clinical Psychopharmacology. 15 (1): 20–2. doi:10.1097/00004714-199502000-00004. PMID 7714223.
  4. Stephen M. Sorensen, EP 0317933 (1989 to Merrell Dow Pharmaceuticals Inc.).
  5. Francis P. Miller, Albert A. Carr, EP 0319962 (1989 to Merrell Dow Pharmaceuticals Inc.).
  6. Paul J. Schechter, John M. Orwin, Christian Karl Hinze, EP 0325063 (1994 to Merrell Dow Pharmaceuticals Inc.).
  7. Albert A. Carr, Norbert L. Wiech, EP 0208235 (1990 to Merrell Dow Pharmaceuticals Inc.).
  8. Albert A. Carr, Norbert L. Wiech, U.S. Patent 4,783,471 (1988 to Merrell Dow Pharmaceuticals Inc.).



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