Mazapertine

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

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
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL10085
ChemSpider	54808
PubChem CID	60820
UNII	N0X1XW704P
CompTox Dashboard (EPA)	DTXSID40158594
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	421.585 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 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

1. 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.
2. 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. S2CID 45947831.
3. 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.