ContaminantDB: Quinacrine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:24:58 UTC

Update Date

2016-11-09 01:17:27 UTC

Accession Number

CHEM022234

Identification

Common Name

Quinacrine

Class

Small Molecule

Description

A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methoxy-6-chloro-9-diethylaminopentylaminoacridine	ChEBI
3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine	ChEBI
6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine	ChEBI
Mepacrine	ChEBI
N(4)-(6-Chloro-2-methoxy-9-acridinyl)-N(1),N(1)-diethyl-1,4-pentanediamine	ChEBI
Quinacrin	Kegg
Quinacrine dihydrochloride	HMDB, MeSH
Monomesylate, quinacrine	MeSH, HMDB
Quinacrine dimesylate	MeSH, HMDB
Quinacrine, (R)-isomer	MeSH, HMDB
Acrichine	MeSH, HMDB
Dihydrochloride, quinacrine	MeSH, HMDB
Dimesylate, quinacrine	MeSH, HMDB
Quinacrine hydrochloride	MeSH, HMDB
Quinacrine monoacetate	MeSH, HMDB
Quinacrine monomesylate	MeSH, HMDB
Atebrin	MeSH, HMDB
Monohydrochloride, quinacrine	MeSH, HMDB
Quinacrine dihyrochloride, (S)-isomer	MeSH, HMDB
Quinacrine monohydrochloride	MeSH, HMDB
Quinacrine, (+-)-isomer	MeSH, HMDB
Quinacrine, (S)-isomer	MeSH, HMDB
Atabrine	MeSH, HMDB
Hydrochloride, quinacrine	MeSH, HMDB
Monoacetate, quinacrine	MeSH, HMDB
Quinacrine dihydrochloride, dihydrate	MeSH, HMDB
Quinacrine dihyrochloride, (R)-isomer	MeSH, HMDB

Chemical Formula

C₂₃H₃₀ClN₃O

Average Molecular Mass

399.957 g/mol

Monoisotopic Mass

399.208 g/mol

CAS Registry Number

83-89-6

IUPAC Name

6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine

Traditional Name

6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine

SMILES

CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2

InChI Identifier

InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)

InChI Key

GPKJTRJOBQGKQK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridines

Alternative Parents

Substituents

Acridine
Haloquinoline
Chloroquinoline
Anisole
Alkyl aryl ether
Aryl chloride
Aryl halide
Pyridine
Benzenoid
Secondary ketimine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:8711 )
aromatic ether (CHEBI:8711 )
organochlorine compound (CHEBI:8711 )
acridines (CHEBI:8711 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	6.13	ALOGPS
logP	5.15	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	10.33	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.39 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.96 m³·mol⁻¹	ChemAxon
Polarizability	46.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9025000000-fbef6d955948eb7f2a3f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0009200000-6e09844cb8551172f45c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0009200000-242960dc93e3658182f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0019100000-85abeddd06ff2cce1fc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0000900000-171d21b8fffe35f493d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udl-0423900000-9f5ab94c444b1766bd01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0934000000-afa177ceaf2f17c89180	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0964000000-cb8056f84bdb3a200fba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0591000000-00e303f9525d62f012d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-171d21b8fffe35f493d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udl-0423900000-9f5ab94c444b1766bd01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0964000000-cb8056f84bdb3a200fba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-0934000000-afa177ceaf2f17c89180	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009200000-242960dc93e3658182f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0019100000-85abeddd06ff2cce1fc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009200000-6e09844cb8551172f45c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0006-0591000000-00e303f9525d62f012d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0006-0591000000-ec7a34b139a1f19af5f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009200000-d6edfe4dda8af03dcf55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0002900000-f41646003acc390ed8bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfu-4975600000-ad273f8cfc82a9f76e9e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-009f-9251000000-556ea0aa9d5a370006a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-b9379b7c57314e49af30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0019000000-79e7dea5a1914a86d008	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9065000000-35833408615f0d3aa74a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-f4b3bd614216642b1025	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

ATABRINE

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Quinacrine

Chemspider ID

232

ChEBI ID

8711

PubChem Compound ID

Not Available

Kegg Compound ID

C07339

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11339632

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11908878

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19747949

Quinacrine (CHEM022234)

Structure for CHEM022234: Quinacrine