Glemanserin

Glemanserin
Clinical data
ATC code	None;
Identifiers
	IUPAC name α-phenyl-1-(2-phenylethyl)-4-piperidine methanol;
CAS Number	132553-86-7;
PubChem CID	71781;
ChemSpider	64815;
UNII	X96LS7MC5Z;
CompTox Dashboard (EPA)	DTXSID4042624 ;
Chemical and physical data
Formula	C20H25NO
Molar mass	295.426 g·mol−1
3D model (JSmol)	Interactive image;
	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;

Glemanserin (INN) (developmental code name MDL-11,939) is a drug which acts as a potent and selective 5-HT_2A receptor antagonist.^[1] The first truly selective 5-HT_2A ligand to be discovered, glemanserin resulted in the development of the widely used and even more potent and selective 5-HT_2A receptor antagonist volinanserin (MDL-100,907), which is a fluorinated analogue.^[2] Though it was largely superseded in scientific research by volinanserin, glemanserin was investigated clinically for the treatment of generalized anxiety disorder.^[3] However, it was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]

Patented Use

Synthesis

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).

References

^ 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.
^ Berend Olivier (10 July 1997). Serotonin Receptors and Their Ligands. Elsevier. p. 167. ISBN 978-0-444-82041-9. Retrieved 6 May 2012.
^ ^a ^b 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.
^ Stephen M. Sorensen, EP 0317933 (1989 to Merrell Dow Pharmaceuticals Inc.).
^ Francis P. Miller, Albert A. Carr, EP 0319962 (1989 to Merrell Dow Pharmaceuticals Inc.).
^ Paul J. Schechter, John M. Orwin, Christian Karl Hinze, EP 0325063 (1994 to Merrell Dow Pharmaceuticals Inc.).
^ Albert A. Carr, Norbert L. Wiech, EP 0208235 (1990 to Merrell Dow Pharmaceuticals Inc.).
^ Albert A. Carr, Norbert L. Wiech, U.S. patent 4,783,471 (1988 to Merrell Dow Pharmaceuticals Inc.).

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[Dudley1988-1] 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.

[Olivier1997-2] Berend Olivier (10 July 1997). Serotonin Receptors and Their Ligands. Elsevier. p. 167. ISBN 978-0-444-82041-9. Retrieved 6 May 2012.

[pmid7714223-3] 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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Patented Use

Synthesis

See also

References