Volinanserin

Volinanserin
Clinical data
ATC code	None;
Identifiers
	IUPAC name (R)-(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]-4-piperidyl]methanol;
Synonyms	MDL-100,907
CAS Number	139290-65-6;
PubChem CID	5311271;
IUPHAR/BPS	185;
ChemSpider	4470782;
UNII	EW71EE171J;
ChEMBL	CHEMBL74355;
ECHA InfoCard	100.123.797
Chemical and physical data
Formula	C22H28FNO3
Molar mass	373.46 g/mol
3D model (Jmol)	Interactive image;
	SMILES c3cc(F)ccc3CCN(CC2)CCC2C(O)c(c1OC)cccc1OC ;

Volinanserin (INN) (developmental code name 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]

References[edit]

^ Schmidt CJ, Fadayel GM, Sullivan CK, Taylor VL (November 1992). "5-HT2 receptors exert a state-dependent regulation of dopaminergic function: studies with MDL 100,907 and the amphetamine analogue, 3,4-methylenedioxymethamphetamine". European Journal of Pharmacology. 223 (1): 65–74. doi:10.1016/0014-2999(92)90819-P. PMID 1362159.
^ Herth MM, Kramer V, Piel M, Palner M, Riss PJ, Knudsen GM, Rösch F (April 2009). "Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET". Bioorganic & Medicinal Chemistry. 17 (8): 2989–3002. doi:10.1016/j.bmc.2009.03.021. PMID 19329329.
^ Nic Dhonnchadha BA, Fox RG, Stutz SJ, Rice KC, Cunningham KA (April 2009). "Blockade of the serotonin 5-HT2A receptor suppresses cue-evoked reinstatement of cocaine-seeking behavior in a rat self-administration model". Behavioral Neuroscience. 123 (2): 382–96. doi:10.1037/a0014592. PMID 19331461.
^ Offord SJ, Wong DF, Nyberg S (August 1999). "The role of positron emission tomography in the drug development of M100907, a putative antipsychotic with a novel mechanism of action". Journal of Clinical Pharmacology. Suppl: 17S–24S. PMID 10434243.
^ Dennis S. Charney; Eric J. Nestler; Pamela Sklar; Joseph D. Buxbaum (July 2013). Neurobiology of Mental Illness. OUP USA. p. 767. ISBN 9780199934959.
^ Marek GJ, Martin-Ruiz R, Abo A, Artigas F (December 2005). "The selective 5-HT2A receptor antagonist M100907 enhances antidepressant-like behavioral effects of the SSRI fluoxetine". Neuropsychopharmacology. 30 (12): 2205–15. doi:10.1038/sj.npp.1300762. PMID 15886717.
^ Teegarden BR, Al Shamma H, Xiong Y (2008). "5-HT(2A) inverse-agonists for the treatment of insomnia". Current Topics in Medicinal Chemistry. 8 (11): 969–76. doi:10.2174/156802608784936700. PMID 18673166.

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[pmid1362159-1] Schmidt CJ, Fadayel GM, Sullivan CK, Taylor VL (November 1992). "5-HT2 receptors exert a state-dependent regulation of dopaminergic function: studies with MDL 100,907 and the amphetamine analogue, 3,4-methylenedioxymethamphetamine". European Journal of Pharmacology. 223 (1): 65–74. doi:10.1016/0014-2999(92)90819-P. PMID 1362159.

[pmid19329329-2] Herth MM, Kramer V, Piel M, Palner M, Riss PJ, Knudsen GM, Rösch F (April 2009). "Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET". Bioorganic & Medicinal Chemistry. 17 (8): 2989–3002. doi:10.1016/j.bmc.2009.03.021. PMID 19329329.

[pmid19331461-3] Nic Dhonnchadha BA, Fox RG, Stutz SJ, Rice KC, Cunningham KA (April 2009). "Blockade of the serotonin 5-HT2A receptor suppresses cue-evoked reinstatement of cocaine-seeking behavior in a rat self-administration model". Behavioral Neuroscience. 123 (2): 382–96. doi:10.1037/a0014592. PMID 19331461.

[pmid10434243-4] Offord SJ, Wong DF, Nyberg S (August 1999). "The role of positron emission tomography in the drug development of M100907, a putative antipsychotic with a novel mechanism of action". Journal of Clinical Pharmacology. Suppl: 17S–24S. PMID 10434243.

[nmi-5] Dennis S. Charney; Eric J. Nestler; Pamela Sklar; Joseph D. Buxbaum (July 2013). Neurobiology of Mental Illness. OUP USA. p. 767. ISBN 9780199934959.

[pmid15886717-6] Marek GJ, Martin-Ruiz R, Abo A, Artigas F (December 2005). "The selective 5-HT2A receptor antagonist M100907 enhances antidepressant-like behavioral effects of the SSRI fluoxetine". Neuropsychopharmacology. 30 (12): 2205–15. doi:10.1038/sj.npp.1300762. PMID 15886717.

[pmid18673166-7] Teegarden BR, Al Shamma H, Xiong Y (2008). "5-HT(2A) inverse-agonists for the treatment of insomnia". Current Topics in Medicinal Chemistry. 8 (11): 969–76. doi:10.2174/156802608784936700. PMID 18673166.

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[5]

[6]

[7]

v t e Antipsychotics (neuroleptics) (N05A)

Typical	Benzamides Levosulpiride Sulpiride Veralipride^‡ Butyrophenones Azaperone Benperidol Bromperidol Droperidol Fluanisone Haloperidol^# Lenperone Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines Clopimozide Fluspirilene Penfluridol Pimozide Phenothiazines Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine) Chloracizine Chlorproethazine Chlorpromazine Cyamemazine Dixyrazine Fluacizine Fluphenazine Levomepromazine/Methotrimeprazine Mesoridazine Perazine Periciazine Perphenazine Perphenazine 4-aminobutyrate Piperacetazine Pipotiazine Prochlorperazine Promazine Promethazine Sulforidazine Thiethylperazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes Chlorprothixene Clopenthixol Clothixamide Flupentixol Fluprothixene Piflutixol Teflutixol Thiothixene Zuclopenthixol Tricyclics Fluotracen Loxapine Trimipramine Others Butaclamol Prothipendyl

Atypical	Benzamides Amisulpride Nemonapride Remoxipride^‡ Sultopride Tiapride Butyrophenones Cinuperone Melperone Setoperone Benzo(iso)oxazole piperidines Iloperidone Ocaperidone^§ Paliperidone Risperidone^# Benzo(iso)thiazole piperazines Lurasidone Perospirone Revospirone^§ Tiospirone^§ Ziprasidone Diphenylbutylpiperazines Amperozide Phenylpiperazines Aripiprazole Aripiprazole lauroxil Bifeprunox^§ Brexpiprazole Cariprazine Tricyclics Amoxapine Asenapine Carpipramine Clocapramine Clorotepine Clotiapine Clozapine^# Flumezapine Fluperlapine Gevotroline Metitepine Mosapramine Olanzapine Quetiapine Tenilapine Zotepine Others Blonanserin Lumateperone^† Molindone Pimavanserin RP5063^† Sertindole Zicronapine^§

Others	Azacyclonol Cannabidiol Oxypertine Reserpine Tetrabenazine

^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Volinanserin

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Clinical data

ATC code	None
Identifiers
IUPAC name (R)-(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]-4-piperidyl]methanol
Synonyms	MDL-100,907
CAS Number	139290-65-6
PubChem CID	5311271
IUPHAR/BPS	185
ChemSpider	4470782
UNII	EW71EE171J
ChEMBL	CHEMBL74355
ECHA InfoCard	100.123.797
Chemical and physical data
Formula	C₂₂H₂₈FNO₃
Molar mass	373.46 g/mol
3D model (Jmol)	Interactive image
SMILES c3cc(F)ccc3CCN(CC2)CCC2C(O)c(c1OC)cccc1OC