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Details

Stereochemistry RACEMIC
Molecular Formula C25H31NO.ClH
Molecular Weight 397.981
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTACLAMOL HYDROCHLORIDE

SMILES

Cl.[H][C@]12C[C@](O)(CCN1C[C@]3([H])C4=C(CCC5=C3C2=CC=C5)C=CC=C4)C(C)(C)C

InChI

InChIKey=QZRUMKUMFJJARD-OMMJFLKZSA-N
InChI=1S/C25H31NO.ClH/c1-24(2,3)25(27)13-14-26-16-21-19-9-5-4-7-17(19)11-12-18-8-6-10-20(23(18)21)22(26)15-25;/h4-10,21-22,27H,11-16H2,1-3H3;1H/t21-,22-,25-;/m1./s1

HIDE SMILES / InChI
Molecular Formula C25H31NO
Molecular Weight 361.5197
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Butaclamol is an antipsychotic drug, which was studied for the treatment of schizophrenia. This drug has never marketed and now is used in research, because of its action as a dopamine receptor-blocking agent. Butaclamol consists of the two forms: (-)-butaclamol, an inactive drug and (+)-butaclamol, a potent neuroleptic drug.

CNS Activity

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
537
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[3H]-DOB(4-bromo-2,5-dimethoxyphenylisopropylamine) and [3H] ketanserin label two affinity states of the cloned human 5-hydroxytryptamine2 receptor.
1990 Nov
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.
1993 Aug
Molecular cloning, characterization, and localization of a high-affinity serotonin receptor (5-HT7) activating cAMP formation.
1993 Sep 15
Pharmacological and functional characterization of D2, D3 and D4 dopamine receptors in fibroblast and dopaminergic cell lines.
1994 Jan
Expression and pharmacological characterization of the human D3 dopamine receptor.
1994 Jan
Characterization of the human dopamine D3 receptor expressed in transfected cell lines.
1994 Jan 1
Neurochemical and functional characterization of the preferentially selective dopamine D3 agonist PD 128907.
1995 Dec
Lack of discrimination by agonists for D2 and D3 dopamine receptors.
1995 Jul
Identification and pharmacological characterization of [125I]L-750,667, a novel radioligand for the dopamine D4 receptor.
1996 Dec
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.
1998 Aug 21
Patents

Patents

20030015197
10
US20120035203
2

Sample Use Guides

In Vivo Use Guide
Maximum clinical response appeared to be at the 20-40 mg. dose level. Extrapyramidal signs occurred at all doses, but with greater severity at higher doses. Excessive daytime drowsiness occurred in all groups but with longer duration and greater intensity in the 20 mg. group.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Curator's Comment: The effects of the two enantiomers of butaclamol and of several neuroleptics on the apomorphine-elicited inhibition of synaptosomal tyrosine hydroxylase activity was investigated. The (+) but not the (-) enantiomer of butaclamol reverses the apomorphine-elicited enzyme inhibition. (+) Butaclamol is more potent than the other tested neuroleptics.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:15:38 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:38 GMT 2023
Record UNII
8TUG8SF12T
Record Status Validated (UNII)
Record Version
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Name Type Language
BUTACLAMOL HYDROCHLORIDE
USAN  
USAN  
Official Name English
BUTACLAMOL HYDROCHLORIDE [USAN]
Common Name English
AY 23028
Code English
BUTACLAMOL HCL
Common Name English
(±)-3.ALPHA.-TERT-BUTYL-2,3,4,4A.BETA.,8,9,13B.ALPHA.,14-OCTAHYDRO-1H-BENZO(6,7)-CYCLOHEPTA(1,2,3-DE)PYRIDO(2,1-A)ISOQUINOLIN-3-OL HYDROCHLORIDE
Common Name English
1H-BENZO(6,7)CYCLOHEPTA(1,2,3-DE)-PYRIDO(2,1-A)ISOQUINOLIN-3-OL, 3-(1,1-DIMETHYLETHYL)-2,3,4,4A,8,9,13B,14-OCTAHYDRO-, HYDROCHLORIDE, (3.ALPHA.,4A.ALPHA.,13B.BETA.)-(±)-
Common Name English
AY 23,028
Code English
AY-23028
Code English
1H-BENZO(6,7)CYCLOHEPTA(1,2,3-DE)-PYRIDO(2,1-A)ISOQUINOLIN-3-OL, 3-(1,1-DIMETHYLETHYL)-2,3,4,4A,8,9,13B,14-OCTAHYDRO-, (3.ALPHA.,4A.ALPHA.,13B.BETA.)-(±)-, HYDROCHLORIDE
Common Name English
AY-23,028
Code English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Fri Dec 15 15:15:38 GMT 2023 , Edited by admin on Fri Dec 15 15:15:38 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C81089
Created by admin on Fri Dec 15 15:15:38 GMT 2023 , Edited by admin on Fri Dec 15 15:15:38 GMT 2023
PRIMARY
FDA UNII
8TUG8SF12T
Created by admin on Fri Dec 15 15:15:38 GMT 2023 , Edited by admin on Fri Dec 15 15:15:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL8514
Created by admin on Fri Dec 15 15:15:38 GMT 2023 , Edited by admin on Fri Dec 15 15:15:38 GMT 2023
PRIMARY
PUBCHEM
37460
Created by admin on Fri Dec 15 15:15:38 GMT 2023 , Edited by admin on Fri Dec 15 15:15:38 GMT 2023
PRIMARY
CAS
36504-94-6
Created by admin on Fri Dec 15 15:15:38 GMT 2023 , Edited by admin on Fri Dec 15 15:15:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID0045757
Created by admin on Fri Dec 15 15:15:38 GMT 2023 , Edited by admin on Fri Dec 15 15:15:38 GMT 2023
PRIMARY
Related Record Type Details
Structure of BUTACLAMOL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BUTACLAMOL
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