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Acridine Orange hydrochloride

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Identification
Molecular formula
C17H19ClN3O2Cl2
CAS number
65-61-2
IUPAC name
N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine;dihydrochloride
State
State

At room temperature, Acridine Orange hydrochloride is in a solid state. It is typically stored in powder form.

Melting point (Celsius)
237.00
Melting point (Kelvin)
510.15
Boiling point (Celsius)
281.00
Boiling point (Kelvin)
554.15
General information
Molecular weight
394.38g/mol
Molar mass
394.3830g/mol
Density
0.9200g/cm3
Appearence

Acridine Orange hydrochloride appears as a dark green crystalline powder in its solid form. It is fluorescent and can appear orange under a fluorescent light due to its staining properties.

Comment on solubility

Solubility of N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine; dihydrochloride

The solubility of the compound N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine; dihydrochloride, with the formula C17H19ClN3O2Cl2, is primarily influenced by its ionic nature and structural characteristics. Being a dihydrochloride salt suggests that it has increased solubility in polar solvents, particularly water.

  • High solubility in water: Compounds of this type often display good solubility due to the presence of multiple ionic (chloride) and polar functional groups.
  • Effect of temperature: Solubility may increase with temperature, which is a common trait among many salts.
  • Solvent interactions: The presence of polar groups such as the methoxy and amine functionalities enhances interactions with water molecules, facilitating solubility.

Therefore, when considering the practical applications or biological interactions of this compound, one can expect that its solubility profile will favor its dissolution in aqueous environments, making it potentially useful in pharmacological settings or as a soluble reagent in synthetic chemistry.

Interesting facts

Exploring N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine; dihydrochloride

This compound, a fascinating amalgamation of acridine and pentane structural motifs, offers a myriad of chemical and biological possibilities. Here are some intriguing facts that shed light on its significance:

  • Pharmacological Interest: The acridine moiety is known for its role in medicinal chemistry. Compounds like this one often exhibit essential pharmacophores that can influence biological activity, particularly in fields related to oncology and molecular biology.
  • Structure-Activity Relationship (SAR): In the context of drug design, understanding how modifications to each part of the molecule alter its action is crucial. The presence of the chloro and methoxy groups on the acridine core can dramatically affect lipophilicity and receptor interactions.
  • Dual Functionality: With both an amine and an acridine component, this compound may serve as a versatile synthetic intermediate, paving the way for the development of complex organic molecules or functional materials.
  • Potential in Anticancer Research: The acridine derivatives are particularly notable in cancer research. Studies suggest that certain acridine-based compounds show promise as antitumor agents by intercalating with DNA, thereby disrupting replication processes.
  • Highlight on Solubility:** The dihydrochloride form enhances solubility in aqueous environments, making it more amenable for in vitro and pharmacokinetic studies.

As we continue to explore and unravel the complexities of compounds like N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine; dihydrochloride, we remain excited about their potential applications in medicine and material science. Each structural feature opens new avenues for research and discovery, affirming the essential role of chemistry in innovation.

Synonyms
QUINACRINE DIHYDROCHLORIDE
69-05-6
Quinacrine hydrochloride
Chemiochin
Atebrine
Mepacrine dihydrochloride
Crinodora
Metoquin
Metoquine
Quinacrine 2HCl
Atabrine dihydrochloride
Mepacrine hydrochloride
Malaricida
Methoquine
Italchin
Metochin
Palacrin
Palusan
Pentilen
Mecryl
Atebrin hydrochloride
Quinacrine hydrochloride anhydrous
Chinacrin hydrochloride
Atabrine hydrochloride
Quinacrine (dihydrochloride)
CCRIS 4709
2-Methoxy-6-chloro-9-(4-diethylamino-1-methylbutylamino)acridine dihydrochloride
Giardiasis (TN)
EINECS 200-700-8
NSC 14229
SN 390
S.N. 390
81A613ZZ6X
866 R.P.
3-Chloro-9-(4'-diethylamino-1'-methylbutylamino)-7-methoxyacridine dihydrochloride
6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine dihydrochloride
N4-(6-chloro-2-methoxyacridin-9-yl)-N1,N1-diethylpentane-1,4-diamine dihydrochloride
Arichin
3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine dihydrochloride
2-Chloro-5-(omega-diethylamino-alpha-methylbutylamino)-7-methoxyacridine dihydrochloride
69-05-6 (HCl)
MEPACRINE HYDROCHLORIDE [WHO-DD]
MEPACRINE HYDROCHLORIDE ANHYDROUS
ANHYDROUS MEPACRINE DIHYDROCHLORIDE
NSC-14229
Acridine, 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxy-, dihydrochloride
6-Chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]-2-methoxyacridine dihydrochloride
(+/-)-6-CHLORO-9-((4-(DIETHYLAMINO)-1-METHYLBUTYL)AMINO)-2-METHOXYACRIDINE DIHYDROCHLORIDE
NSC14229
NSC-757307
QUINACRINE HYDROCHLORIDE [VANDF]
Giardiasis
UNII-81A613ZZ6X
SR-01000075643
Quinacrine diHCl
Acridine, 6-chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]-2-methoxy-, dihydrochloride
intercalating agent
Mepacrine dihydrochloride;SN-390
ATEBEIN
(+/-)-6-CHLORO-9-((4-(DIETHYLAMINO)-1-METHYLBUTYL)AMINO)-2-METHOXYACRIDINE DIHYDROCHLORIDE DIHYDRATE
Quinacrine, Dihydrochloride
ATEBRINE HYDROCHLORIDE
SCHEMBL498442
SPECTRUM1500522
QUINACRINEDIHYDROCHLORIDE
CHEMBL554190
DTXSID6025985
Quinacrine dihydrochloride hydrate
HMS1920N16
HY-13735AR
GCA10041
GCA10042
Quinacrine dihydrochloride, >=90%
Tox21_500970
CCG-39896
HY-13735A
s4255
AKOS005111333
CS-4590
FC76313
KH-0002
LP00970
1,4-Pentanediamine, N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, dihydrochloride
Quinacrine (dihydrochloride) (Standard)
NCGC00094270-01
NCGC00094270-02
NCGC00094270-03
NCGC00261655-01
866 R. P.
DB-055218
S. N. 390
EU-0100970
Q0056
SW196810-3
D02548
H12040
Q 3251
SR-01000075643-1
Q27269238
3-CHLORO-7-METHOXY-9-(1-METHYL-4-DIETHYLAMINOBUTYLAMINO) ACRIDINE DIHYDROCHLORIDE
3-CHLORO-9-(4'-DIETHYLAMINO-1'-METHYLBUTYLAMINO)-7-METHOXY ACRIDINE DIHYDROCHLORIDE
4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine;dihydrochloride
6-Chloro-9-(4-diethylamino-1-methylbutyl)amino-2-methoxyacridine Dihydrochloride
6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine dihydrochloride
200-700-8
N~4~-(6-chloro-2-methoxyacridin-9-yl)-N~1~,N~1~-diethylpentane-1,4-diamine dihydrochloride