Mazapertine

Mazapertine
Names

IUPAC name Piperidin-1-yl[3-({4-[2-(propan-2-yloxy)phenyl]piperazin-1-yl}methyl)phenyl]methanone
Other names RWJ-37796
Identifiers
CAS Number	134208-17-6^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL10085
ChemSpider	54808
PubChem	60820
UNII	N0X1XW704P
InChI InChI=1S/C26H35N3O2/c1-21(2)31-25-12-5-4-11-24(25)28-17-15-27(16-18-28)20-22-9-8-10-23(19-22)26(30)29-13-6-3-7-14-29/h4-5,8-12,19,21H,3,6-7,13-18,20H2,1-2H3 Key: ZKZFPRUSWCYSGT-UHFFFAOYSA-N InChI=1/C26H35N3O2/c1-21(2)31-25-12-5-4-11-24(25)28-17-15-27(16-18-28)20-22-9-8-10-23(19-22)26(30)29-13-6-3-7-14-29/h4-5,8-12,19,21H,3,6-7,13-18,20H2,1-2H3 Key: ZKZFPRUSWCYSGT-UHFFFAOYAF
SMILES O=C(N1CCCCC1)c2cc(ccc2)CN4CCN(c3ccccc3OC(C)C)CC4
Properties
Chemical formula	C₂₆H₃₅N₃O₂
Molar mass	421.59 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

Mazapertine (RWJ-37796) is an antipsychotic agent that was developed by Johnson & Johnson but never marketed. It exerts its pharmacological effect through affinity for dopamine D₂, serotonin 5-HT_1A, and α₁-adrenergic receptors.^[1]

Mazapertine is safe and well tolerated when administered orally.^[2]

Analogs of mazapertine with conformational restriction have been prepared and have greater affinity for the 5-HT_1A receptor.^[3]

References

↑ Reitz, A. B.; Baxter, E. W.; Codd, E. E.; Davis, C. B.; Jordan, A. D.; Maryanoff, B. E.; Maryanoff, C. A.; McDonnell, M. E.; Powell, E. T.; Renzi, M. J.; Schott, M. R.; Scott, M. K.; Shank, R. P.; Vaught, J. L. (1998). "Orally Active Benzamide Antipsychotic Agents with Affinity for Dopamine D2, Serotonin 5-HT1A, and Adrenergic α1Receptors". Journal of Medicinal Chemistry. 41 (12): 1997–2009. doi:10.1021/jm970164z. PMID 9622541.
↑ Kleinbloesem, C. H.; Jaquet-Müller, F. O.; Al-Hamdan, Y.; Baldauf, C.; Gisclon, L.; Wesnes, K.; Curtin, C. R.; John Stubbs, R.; Walker, S. A.; Brunner-Ferber, F. O. (1996). "Incremental dosage of the new antipsychotic mazapertine induces tolerance to cardiovascular and cognitive effects in healthy men*". Clinical Pharmacology & Therapeutics. 59 (6): 675–685. doi:10.1016/S0009-9236(96)90008-9. PMID 8681493.
↑ Baxter, Ellen W.; Reitz, Allen B. (1997). "Hindered rotation congeners of mazapertine: High affinity ligands for the 5-HT1A receptor". Bioorganic & Medicinal Chemistry Letters. 7 (7): 763. doi:10.1016/S0960-894X(97)00074-7.

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

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