Butaclamol

Butaclamol (AY-23,028) is a typical antipsychotic which was never marketed.[1] Sold as the hydrochloride salt for use in research, the compound acts as a dopamine receptor antagonist.[2]

Butaclamol
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (3S,4aS,13bS)-3-(2-Methyl-2-propanyl)-2,3,4,4a,8,9,13b,14-octahydro-1H-benzo[6,7]cyclohepta[1,2,3-de]pyrido[2,1-a]isoquinolin-3-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H31NO
Molar mass361.529 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)(C)C1(CCN2CC3C4=CC=CC=C4CCC5=C3C(=CC=C5)C2C1)O

Chemistry

pKa = 7.15 (uncorrected for ionic strength)[3]

References
  1. Buckingham J (1985). Dictionary of organic compounds - Google Books. ISBN 978-0-412-54090-5.
  2. Hall DA, Strange PG (June 1997). "Evidence that antipsychotic drugs are inverse agonists at D2 dopamine receptors". British Journal of Pharmacology. 121 (4): 731–6. doi:10.1038/sj.bjp.0701196. PMC 1564749. PMID 9208141.
  3. Chrzanowski FA, McGrogan BA, Maryanoff BE (March 1985). "The pKa of butaclamol and the mode of butaclamol binding to central dopamine receptors". Journal of Medicinal Chemistry. 28 (3): 399–400. doi:10.1021/jm00381a022. PMID 2579238.
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