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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H27N5O4.ClH
Molecular Weight 473.953
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLAZOSIN HYDROCHLORIDE

SMILES

Cl.COC1=CC2=C(C=C1OC)C(N)=NC(=N2)N3CCN([C@H]4CCCC[C@@H]34)C(=O)C5=CC=CO5

InChI

InChIKey=SKDIDWRQDBIQBS-MCJVGQIASA-N
InChI=1S/C23H27N5O4.ClH/c1-30-19-12-14-15(13-20(19)31-2)25-23(26-21(14)24)28-10-9-27(16-6-3-4-7-17(16)28)22(29)18-8-5-11-32-18;/h5,8,11-13,16-17H,3-4,6-7,9-10H2,1-2H3,(H2,24,25,26);1H/t16-,17+;/m0./s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18037913 | https://www.ncbi.nlm.nih.gov/pubmed/15598431

CYCLAZOSIN HYDROCHLORIDE is a quinazoline derivative pharmacologically characterized as putative a1B-adrenoceptor antagonist.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.24 nM [Ki]
12.3 nM [Ki]
0.135 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Synthesis and alpha(1)-adrenoceptor antagonist activity of derivatives and isosters of the furan portion of (+)-cyclazosin.
2007-03-15
Synthesis and biological profile of the enantiomers of [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-cis-octahydroquinoxalin- 1-yl]furan-2-ylmethanone (cyclazosin), a potent competitive alpha 1B- adrenoceptor antagonist.
1996-11-08
Patents

Sample Use Guides

Male C-57 WT mice (22–35 g) were injected s.c. with the putative a1B-adrenoceptor antagonist cyclazosin (1.0mg/kg). Cyclazosin was administered 30 min prior to the injection of vehicle (1 ml/kg) or MDMA (20mg/kg). The putative a1B-adrenoceptor antagonist cyclazosin (1mg/kg) in vehicle experiments did not significantly alter the body temperature when compared to vehicle group. The pretreatment of mice with cyclazosin significantly altered the effect of MDMA on core body temperature
Route of Administration: Topical
Sections of the abdominal aorta, obtained from adult female New Zealand rabbits, were treated with agonists and antagonists of adrenergic receptors. Administration of cyclazosin at a dose of 0.002 μM caused a decrease in the muscle tonus of -0.49 ± 0.10 mN. After blockade of the α1B-adrenergic receptor by 0.02 mkM cyclazosin, the administration of 0.05 μM phenylephrine resulted in an increase of the aortic muscle tonus of 1.49 ± 0.14 mN.
Name Type Language
CYCLAZOSIN HYDROCHLORIDE
Common Name English
(+)-CYCLAZOSIN HYDROCHLORIDE
Preferred Name English
METHANONE, ((4AR,8AS)-4-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)OCTAHYDRO-1(2H)-QUINOXALINYL)-2-FURANYL-, HYDROCHLORIDE (1:1), REL-
Systematic Name English
QUINOXALINE, 1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-(2-FURANYLCARBONYL)DECAHYDRO-, MONOHYDROCHLORIDE, CIS-
Common Name English
((4AR,8AS)-4-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)-2,3,4A,5,6,7,8,8A-OCTAHYDROQUINOXALIN-1-YL)-(FURAN-2-YL)METHANONE HYDROCHLORIDE
Systematic Name English
QUINOXALINE, 1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-(2-FURANYLCARBONYL)DECAHYDRO-, MONOHYDROCHLORIDE, (4AR,8AS)-REL-
Systematic Name English
((4AR,8AS)-4-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)OCTAHYDRO-1(2H)-QUINOXALINYL)(2-FURYL)METHANONE HYDROCHLORIDE (1:1)
Systematic Name English
CYCLAZOSIN HCL
Common Name English
((4AR,8AS)-4-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)OCTAHYDROQUINOXALIN-1(2H)-YL)(2-FURYL)METHANONE HYDROCHLORIDE
Systematic Name English
(4-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)-CIS-OCTAHYDROQUINOXALIN-L-YL)FURAN-2-YLMETHANONE HYDROCHLORIDE
Common Name English
Code System Code Type Description
PUBCHEM
9869475
Created by admin on Mon Mar 31 22:27:49 GMT 2025 , Edited by admin on Mon Mar 31 22:27:49 GMT 2025
PRIMARY
EPA CompTox
DTXSID1040453
Created by admin on Mon Mar 31 22:27:49 GMT 2025 , Edited by admin on Mon Mar 31 22:27:49 GMT 2025
PRIMARY
CAS
146929-33-1
Created by admin on Mon Mar 31 22:27:49 GMT 2025 , Edited by admin on Mon Mar 31 22:27:49 GMT 2025
PRIMARY
FDA UNII
RLN802138L
Created by admin on Mon Mar 31 22:27:49 GMT 2025 , Edited by admin on Mon Mar 31 22:27:49 GMT 2025
PRIMARY
CAS
184033-31-6
Created by admin on Mon Mar 31 22:27:49 GMT 2025 , Edited by admin on Mon Mar 31 22:27:49 GMT 2025
ALTERNATIVE