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Butaclamol

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Butaclamol
Clinical data
ATC code
  • none
Identifiers
  • (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
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC25H31NO
Molar mass361.529 g·mol−1
3D model (JSmol)
  • CC(C)(C)C1(CCN2CC3C4=CC=CC=C4CCC5=C3C(=CC=C5)C2C1)O

Butaclamol (AY-23,028) is a type ofantipsychotic which was never marketed.[1] Sold as the hydrochloride salt for use in research, the compound acts as adopamine receptorantagonist.[2]

Discussion

[edit]

pKa = 7.15 (uncorrected forionic strength)[3]

McN-4171 is an analog ofbutaclamol.[3][4]McN-4612-Y is also described in the attached article. This is similar toMcN 4612-z except it is the opposite optical antipode. It is therefore supposedly an antipsychotic.

Synthesis

[edit]

The synthesis has been reported:[5][6][7] Patent:[8]

  • The starting material is made by aFavorskii reaction ofdibenzosuberone withacetylene followed by aMeyer–Schuster rearrangement to the aldehyde and oxidation to the acid. Another method isReformatsky reaction with bromoethylacetate and catalytic hydrogenation of the olefin in the ester that follows dehydration.
  • The starting material is called 10,11-Dihydro-5H-dibenzo-[a,d]cycloheptene-5-acetic acid, PC12669091 (1). FGI by any of a number of methods to theisocyanate (NCO) gives (2). Addition of one equivalent of water gives N-formyl-10,11-dihydro-5H-dibenzo(a,d)cycloheptene-5-methylamine (3). Cyclization gives 1,7,8,12b-tetrahydrobenzo(6,7)cyclohept(1,2,3-de)isoquinoline [7574-72-3] (4). A modifiedRobinson annulation withmethylvinylketone gave PC21397166 (5).

See also

[edit]

References

[edit]
  1. ^Buckingham J (1985).Dictionary of organic compounds - Google Books. CRC Press.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. ^abChrzanowski 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.
  4. ^Kukla, M. J., Bloss, J. L., Brougham, L. R. (April 1979)."Use of the butaclamol template in a search for antipsychotic agents with lessened side effects".Journal of Medicinal Chemistry.22 (4):401–406.doi:10.1021/jm00190a009.
  5. ^Chronicles of Drug Discovery, Volume 1, Edited by Jasjit S. Bindra and Daniel Lednicer, page 61, (L. G. Humber).
  6. ^Castañer, J., Chatterjee, S. S. (1976). "Butaclamol".Drugs of the Future.1 (4): 171.doi:10.1358/dof.1976.001.04.64761.
  7. ^Bruderlein, F. T., Humber, L. G., Voith, K. (February 1975). "Neuroleptic agents of the benzocycloheptapyridoisoquinoline series. 1. Syntheses and stereochemical and structural requirements for activity of butaclamol and related compounds".Journal of Medicinal Chemistry.18 (2):185–188.doi:10.1021/jm00236a016.PMID 1168258.
  8. ^Francois T. Bruderlein, US4059585 (1977 to Wyeth Canada ULC).
Typical
Disputed
Atypical
Others
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
σ1
σ2
Unsorted
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
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