Volinanserin

Volinanserin (INN; developmental code MDL-100,907) is a highly selective 5-HT_2A receptor antagonist that is frequently used in scientific research to investigate the function of the 5-HT_2A receptor.^[1][2][3] It was also tested in clinical trials as a potential antipsychotic,^[4][5] antidepressant,^[6] and treatment for insomnia but was never marketed.^[7]

Volinanserin

Clinical data
Other names	MDL-100,907; M100907
ATC code	None
Identifiers
IUPAC name (R)-(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]-4-piperidyl]methanol
CAS Number	139290-65-6
PubChem CID	5311271
IUPHAR/BPS	185
ChemSpider	4470782
UNII	EW71EE171J
ChEMBL	ChEMBL74355
CompTox Dashboard (EPA)	DTXSID6047363
ECHA InfoCard	100.123.797
Chemical and physical data
Formula	C22H28FNO3
Molar mass	373.468 g·mol−1
3D model (JSmol)	Interactive image
SMILES c3cc(F)ccc3CCN(CC2)CCC2C(O)c(c1OC)cccc1OC

CNS Review:^[8]

Synthesis

The synthesis of volinanserin has been reported.^{[9][10][11][12]} Beginning with protection of ethyl isonipecotate (1) with Boc anhydride gives ethyl N-Boc-4-piperidinecarboxylate (2). Ester-amide interchange with N-methoxymethylamine HCl in the presence of carbonyldiimidazole (CDI) coupling agent gives 1-Boc-4-[methoxy(methyl)carbamoyl]piperidine (3). Weinreb ketone synthesis occurs upon benzoylation with 1,2-dimethoxybenzene (4) to give 1-Boc-4-(2,3-dimethoxybenzoyl)piperidine (5). Acid removal of the urethane protecting group gives (2,3-dimethoxyphenyl)-piperidin-4-ylmethanone (6). The reduction of the ketone with sodium borohydride leads to (2,3-dimethoxyphenyl)-piperidin-4-ylmethanol (7). Resolution of the alcohol gives (8). S_N2 alkylation of the secondary nitrogen with 4-fluorophenethyl bromide (9) completes the synthesis of volinanserin (10).

Synthesis of volinanserin

See also

• Glemanserin
• Pruvanserin
• Roluperidone
• Lenperone
• Lidanserin
• Ketanserin
• Ritanserin
• Eplivanserin
• Pimavanserin