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Chloroquine

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Identification
Molecular formula
C18H26ClN3O
CAS number
54-05-7
IUPAC name
4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol
State
State

Solid at room temperature. It is usually handled as a crystalline powder and known for its pharmacological activity.

Melting point (Celsius)
87.00
Melting point (Kelvin)
360.15
Boiling point (Celsius)
337.90
Boiling point (Kelvin)
611.05
General information
Molecular weight
319.88g/mol
Molar mass
319.8780g/mol
Density
1.2600g/cm3
Appearence

Chloroquine appears as a white to slightly yellow crystalline powder. It is usually odorless with a bitter taste.

Comment on solubility

Solubility of 4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol

The solubility of the compound 4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol (C18H26ClN3O) is influenced by various structural factors inherent to its chemical makeup.

  • Polarity: The presence of polar functional groups, such as the phenolic -OH and the amine -NH groups, increases the overall polarity of the molecule. This can enhance its solubility in polar solvents like water and alcohols.
  • Hydrophobic Characteristics: The diethylaminomethyl group contributes to hydrophobic interactions, which may limit solubility in highly polar environments but increase compatibility with non-polar solvents.
  • Chlorine Atom: The substitution of chlorine can affect both intermolecular interactions and the overall electronic distribution, potentially influencing solubility profiles in different solvents.
  • Solvent Choice: This compound may demonstrate differential solubility in organic solvents such as acetone, methanol, and dichloromethane, due to its unique blend of hydrophilic and lipophilic properties.

In summary, while 4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol exhibits some solubility in polar solvents, its overall behavior will often be dictated by the environmental conditions and the nature of the solvent used. As the renowned aphorism goes, "Like dissolves like." Therefore, the selection of the solvent is crucial when it comes to maximizing solubility.

Interesting facts

Interesting Facts About 4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol

4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol, often referred to by its functional groups, is a fascinating chemical compound that combines characteristics of both quinoline and phenolic molecules. Here are some key points about this compound:

  • Pharmacological Significance: Compounds like this one are often explored for their potential use in pharmaceuticals, especially in the development of antimicrobial and antiparasitic agents.
  • Structure and Activity: The unique combination of diethylamino and chlorinated quinoline groups lends to interesting biological activities, including interactions with DNA and proteins that can alter metabolic pathways.
  • Research Potential: Its structure suggests it may possess valuable properties for cancer research as derivatives in this family have shown activity against various cancer cell lines.
  • Synthetic Routes: The synthesis of this compound may involve multiple reaction steps, utilizing techniques such as substitution reactions and condensation reactions, showcasing the complex methods required in modern organic chemistry.
  • Toxicological Studies: As with many compounds containing chlorine and amines, there is a need for comprehensive toxicological assessment to establish safe usage profiles in medicinal chemistry.

In summary, 4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol is not only an intriguing structure but also holds promise in various scientific fields, particularly in drug development. Its dual functionality as both an amine and a phenol makes it a versatile candidate for further exploration.

Synonyms
amodiaquine
86-42-0
Amodiaquin
Flavoquine
Camoquin
Camoquine
Camochin
Camoquinal
Miaquin
Amodiaquina
Amodiaquinum
Amodiaquine, ring-closed
Cam-AQ1
Amodiachin
Amodiachinum
Sunoquine
CAM-AQI
4-[(7-CHLOROQUINOLIN-4-YL)AMINO]-2-[(DIETHYLAMINO)METHYL]PHENOL
Amodiaquinum [INN-Latin]
Amodiaquina [INN-Spanish]
4-((7-Chloroquinolin-4-yl)amino)-2-((diethylamino)methyl)phenol
Amodiaquine hydrochloride
SN 10,751
Phenol, 4-[(7-chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]-
Alphaquine
Amdaquine
Amoquin
CHEBI:2674
S. N. 10751
EINECS 201-669-3
NSC 13453
NSC-13453
Amodiaquine [USP:INN:BAN]
GNF-Pf-5648
BRN 0300962
CCRIS 8486
4-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol
4-[(7-Chloro-4-quinolinyl)amino]-2-[(diethylamino)methyl]phenol
HSDB 7457
AMODIAQUIN [MI]
7-Chloro-4-(3-diethylaminomethyl-4-hydroxyanilino)quinoline
AMODIAQUINE [INN]
AMODIAQUINE [HSDB]
7-Chloro-4-(3-diethylaminomethyl-4-hydroxyphenylamino)quinoline
CHEMBL682
AMODIAQUINE [VANDF]
4-((7-Chloro-4-quinolinyl)amino)-2-((diethylamino)methyl)phenol
AMODIAQUINE [MART.]
Phenol, 4-((7-chloro-4-quinolinyl)amino)-2-((diethylamino)methyl)-
AMODIAQUINE [WHO-DD]
AMODIAQUINE [WHO-IP]
220236ED28
DTXSID2022597
4-((7-Chloro-4-quinolyl)amino)-alpha-(diethylamino)-o-cresol
AMODIAQUINE [USP IMPURITY]
AMODIAQUINE [USP MONOGRAPH]
5-22-10-00283 (Beilstein Handbook Reference)
NSC13453
Amodiaquin (dihydrochloride dihydrate)
Amodiaquinum (INN-Latin)
SJ000110703
Amodiaquina (INN-Spanish)
AMODIAQUINE (MART.)
CQA
Amodiaquine (USP:INN:BAN)
Amodiaquine USP24
AMODIAQUINE (USP IMPURITY)
AMODIAQUINE (USP MONOGRAPH)
4-[(7-chloro-4-quinolyl)amino]-alpha-(diethylamino)-o-cresol
4-[(7-Chloro-4-quinolinyl)amino]-.alpha.-(diethylamino)-o-cresol
BDBM50041457
Quinoline, 7-chloro-4-((3-((diethylamino)methyl)-4-hydroxyphenyl)amino)-
Amodiaquini
4-((7-chloroquinolin-4-yl)amino)-2-(diethylaminomethyl)phenol
o-Cresol, 4-((7-chloro-4-quinolyl)amino)-.alpha.-(diethylamino)-
o-Cresol, 4-[(7-chloro-4-quinolyl)amino]-.alpha.-(diethylamino)-
Quinoline, 7-chloro-4-[[3-[(diethylamino)methyl]-4-hydroxyphenyl]amino]-
2aou
UNII-220236ED28
WR-002977
Amodiaquine (USP/INN)
Prestwick0_000309
Prestwick1_000309
Prestwick2_000309
Prestwick3_000309
Epitope ID:131784
Oprea1_019229
SCHEMBL44152
BSPBio_000278
MLS001304065
AMODIAQUINE; FLAVOQUINE
SPBio_002497
USRE49340, Rank 6
BPBio1_000306
DTXCID702597
GTPL10018
HY-B1322A
P01BA06
4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol
BDBM586429
HMS2236K03
HMS3372M02
AMODIAQUINUM [WHO-IP LATIN]
o-Cresol, 4-((7-chloro-4-quinolyl)amino)-alpha-(diethylamino)-
s5948
AKOS000538864
CCG-103317
DB00613
FC17879
NCGC00017063-04
NCGC00017063-07
NCGC00017063-13
NCGC00244901-01
NCGC00244901-04
AC-13295
SMR000718769
DB-056928
CS-0013340
NS00004024
VU0472676-1
C07626
D02922
EN300-708791
G12606
AH-034/11364141
AH-034/33492024
Q239569
BRD-K91290917-300-01-8
BRD-K91290917-336-05-3
4-(3'-diethylaminomethyl-4'-hydroxyanilino)-7-chloroquinoline
4-(7-chloroquinolin-4-ylamino)-2-((diethylamino)methyl)phenol
4-((7-Chloro-4-quinolinyl)amino)-alpha-(diethylamino)-o-cresol
4-((7-Chloro-4-quinolyl)amino)-.alpha.-(diethylamino)-o-cresol
4-[(7-Chloro-4-quinolyl)amino]-a-(diethylamino)-o-cresol;Camochin
1021496-19-4
201-669-3