Basic information
- CAS
37115-32-5- Standard SMILES
CN(C)Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1)=NC2- InChIKey
GJSLOMWRLALDCT-UHFFFAOYSA-N- Molecular formula
- C19H18ClN5
- Average molar mass
- 351.8 g/mol
- Monoisotopic mass
- 351.1250733
Names & identifiers
- Preferred name
- Adinazolam
- IUPAC
- 1-(8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine
- English name
- ADINAZOLAM
- Molecular formula
- C19H18ClN5
- Molecular weight
- 351.83
Names & synonyms
ADINAZOLAM37115-32-5AdinazolamumU-411238-Chloro-1-((dimethylamino)methyl)-6-phenyl-4H-s-triazolo(4,3-a)(1,4)benzodiazepineDTXSID40190611U-41,123KN08449444CHEBI:2514128-chloro-1-[(dimethylamino)methyl]-6-phenyl-4h-s-triazolo[4,3-a][1,4]benzodiazepine((12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo(8.4.0.0^(2,6))tetradeca-1(10),3,5,8,11,13-hexaen-3-yl)methyl)dimethylamine({12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methyl)dimethylamine
Show more names
Adinazolam (CRM)Adinazolam solution8-Chloro-N,N-dimethyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-1-methanamine4H-[1,2,4]Triazolo[4,3-a][1,4]benzodiazepine-1-methanamine, 8-chloro-N,N-dimethyl-6-phenyl-γ-Aminobutyric acid Receptor,sickness,antihistamine,GABA Receptor,inhibit,Adinazolam,U-41123,U 41123,Huntington,Gamma-aminobutyric acid Receptor,anti-motion,piperazine,U41123,Inhibitor
RefChem:553043DTXCID80113102N05BA07Adinazolamum [INN-Latin]Deracyn1-(8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamineU 41123Adinazolam [USAN]
Database identifiers
- CAS
37115-32-5- PubChem CID
- 37632
- DTXSID
DTXSID40190611- ChEMBL
CHEMBL328250- ChEBI
CHEBI:251412- UNII
- KN08449444
- Nikkaji
- J19.718A
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 46.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 490
Experimental & physicochemical properties
LogP
4.4
4.4
Solubility6.72e-02 g/L
Physical DescriptionSolid
Kovats Retention Index3060
Physicochemical properties
- Melting point
- 171 · 171-172.5° (US 4250094); mp 165-166° (DE 2201210)
- Boiling point
- 527 · 527.0±60.0 °C(Predicted)
- Density
- 1.31 · 1.31±0.1 g/cm3(Predicted)
- storage temp.
- -10 to · -10 to -25°C
- pka
- 6.2 · pKa 6.2 (D2O/DClor D2O/NaOD ) (Uncertain);5.8±0.1(D2O/DClor D2O/NaOD ) (Uncertain)
- form
- Solid
- color
- White to off-white
- InChI
- 1S/C19H18ClN5/c1-24(2)12-18-23-22-17-11-21-19(13-6-4-3-5-7-13)15-10-14(20)8-9-16(15)25(17)18/h3-10H,11-12H2,1-2H3
- InChIKey
- GJSLOMWRLALDCT-UHFFFAOYSA-N
- SMILES
- Clc1cc2c(cc1)[n]3c(nnc3CN(C)C)CN=C2c4ccccc4
- FDA UNII
- 8449444 · KN08449444
- ATC code
- 5 BA07 · N05BA07
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H370
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P243-P260-P264-P270-P280-P303+P361+P353-P307+P311-P321-P370+P378-P403+P235-P405-P501
- RIDADR
- 3249 · 3249
- WGK Germany
- 2 · WGK 2
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Safety & regulation
Safety data
- wgk
- WGK 2
- ridadr
- 3249
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS08
- hazard_class
- 6.1(b)
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H225-H370
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P210-P233-P240-P241-P242-P243-P260-P264-P270-P280-P303+P361+P353-P307+P311-P321-P370+P378-P403+P235-P405-P501
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system；N05 - Psycholeptics；N05B - Anxiolytics；N05BA - Benzodiazepine derivatives；N05BA07 - Adinazolam
QN - Nervous system；QN05 - Psycholeptics；QN05B - Anxiolytics；QN05BA - Benzodiazepine derivatives；QN05BA07 - Adinazolam
Pharmacodynamics
Adinazolam is a benzodiazepine derivative used to treat anxiety, status epilepticus, and for sedation induction and anterograde amnesia. Adinazolam binds with high affinity to the GABA benzodiazepine receptor complex. Considerable evidence suggest that the central pharmacologic/therapeutic actions of alprazolam are mediated via interaction with this receptor complex.
Mechanism of Action
Adinazolam binds to peripheral-type benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.
Biological Half-LifeLess than 3 hours.
Metabolism/Metabolites
The drug primarily undergoes hepatic metabolism to form the main metabolite N-desmethyladinazolam, alpha-hydroxyalprazolam, and estazolam.
Adinazolam has known human metabolites that include N-demethyladinazolam.
MeSH Pharmacological Classification
Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.
Cellular LocationsMembrane
Applications
UsesAntidepressant; sedative-hypnotic.
Additional notes
DefinitionChEBI: A triazolo[4,3-a][1,4]benzodiazepine having a dimethylaminomethyl group at the 1-position, a phenyl group at the 6-position and a chloro substituent at the 8-position.
Related reactions
5 records
Compound notes
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