Butaclamol

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	36504-93-5;
PubChem CID	37459;
IUPHAR/BPS	62;
ChemSpider	34364;
UNII	A7A2802VNL;
ChEBI	CHEBI:73298 ;
ChEMBL	ChEMBL479587 ;
CompTox Dashboard (EPA)	DTXSID701317857 DTXSID5048429, DTXSID701317857 ;
Chemical and physical data
Formula	C25H31NO
Molar mass	361.529 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)C1(CCN2CC3C4=CC=CC=C4CCC5=C3C(=CC=C5)C2C1)O;

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

Chemistry

pK_a = 7.15 (uncorrected for ionic strength)^[3]

References

^ Buckingham J (1985). Dictionary of organic compounds - Google Books. CRC Press. ISBN 978-0-412-54090-5.
^ 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.
^ 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.

[urlDictionary_of_organic_compounds_-_Google_Books-1] Buckingham J (1985). Dictionary of organic compounds - Google Books. CRC Press. ISBN 978-0-412-54090-5.

[pmid9208141-2] 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.

[pmid2579238-3] 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.

[1]

[2]

[3]

v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Others/unknown: Azacyclonol Xanomeline/trospium chloride
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III