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Amsacrine

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Identification
Molecular formula
C21H19ClN3O2
CAS number
51264-14-3
IUPAC name
N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine
State
State

Amacrine is a solid at room temperature, existing in the form of crystalline powder.

Melting point (Celsius)
214.00
Melting point (Kelvin)
487.10
Boiling point (Celsius)
503.30
Boiling point (Kelvin)
776.50
General information
Molecular weight
393.85g/mol
Molar mass
393.9430g/mol
Density
1.3490g/cm3
Appearence

Amacrine is an orange/yellow crystalline powder. These crystals are typically finely ground for preparation in scientific or pharmaceutical uses.

Comment on solubility

Solubility Characteristics

The compound N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine (C21H19ClN3O2) exhibits unique solubility properties influenced by its complex molecular structure. Understanding the solubility of this compound is essential for its practical applications. Here are some key points:

  • Polarity: The presence of the methoxy group and the amine functionalities suggests that the compound may exhibit some degree of polarity, potentially impacting its solubility in various solvents.
  • Solvent Compatibility: It is likely soluble in organic solvents such as ethanol, dimethyl sulfoxide (DMSO), and acetonitrile due to its organic nature. However, solubility in water may be limited.
  • Influenced by pH: The solubility of diamines can vary significantly with pH due to their ability to protonate. This means that adjusting the pH can enhance or reduce solubility patterns.
  • Temperature Effects: Generally, increasing temperature can enhance the solubility of solids in liquids, and this compound may respond similarly.

In conclusion, the solubility of N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine is a multifaceted topic that can be significantly influenced by the surrounding environment, including the type of solvent, the presence of ions, and environmental conditions. As with many chemical compounds, careful assessment through experimental data is necessary to fully understand its solubility behavior.

Interesting facts

Interesting Facts About N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine

N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine is a fascinating compound that combines elements of organic chemistry with potential applications in medicinal fields. This compound belongs to the category of substituted acridines, which are known for their vivid histories in various industrial and pharmaceutical applications.

Key Characteristics

  • Multifunctional Drug Candidates: This class of compounds has been extensively studied for its biological activities, particularly as anticancer agents.
  • Structural Diversity: The presence of both chloro and methoxy groups introduces diverse electronic properties that can influence the compound's reactivity and interactions.
  • Potential Antimicrobial Activity: Acridine derivatives often exhibit notable antimicrobial properties, making them subjects of interest in the fight against drug-resistant pathogens.

This compound's design, with distinct substituents, allows for fine-tuning of its pharmacokinetic properties. As emphasized by researchers: "The strategic incorporation of electron-withdrawing and donating groups can lead to enhanced bioactivity." This concept is particularly relevant in drug design, where such modifications can dramatically change a compound's efficacy and safety profile.

Applications and Research

Ongoing research is exploring the use of acridine derivatives in various therapeutic contexts, including:

  • Cancer therapy
  • Antiviral treatments
  • Anti-inflammatory agents

As scientists continue to explore N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine, the compound stands as a testament to the intricate connections between chemical structure and biological function. Its journey from synthesis to application could uncover new horizons in medicinal chemistry.

Synonyms
quinacrine
mepacrine
atabrine
83-89-6
Acrinamine
Acriquine
Akrichin
Antimalarina
Haffkinine
Italchine
Quinactine
Erion
acrichine
Mepacrina
Mepacrinum
Quinacrin
Quinacrine hydrochloride
Mepacrine [INN:BAN]
Mepacrinum [INN-Latin]
Mepacrina [INN-Spanish]
atebrin
St 439
6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine
HSDB 3253
1,4-Pentanediamine, N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-
2-Methoxy-6-chloro-9-diethylaminopentylaminoacridine
3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine
EINECS 201-508-7
H0C805XYDE
Mepacrine (INN)
Malaricida
Methoquine
Italchin
Metochin
Palacrin
Palusan
Pentilen
Mecryl
CCRIS 3726
CCRIS 8633
CHEBI:8711
GNF-PF-5448
AI3-04467
MEPACRINE [INN]
QUINACRINE [MI]
QUINACRINE [HSDB]
QUINACRINE [VANDF]
MEPACRINE [WHO-DD]
CHEMBL7568
Mepacrine hydrochloride
4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine
Acridine, 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxy-
DTXSID7022627
Quinacrine (hydrochloride,hydrate)
chinacrin
N4-(6-Chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-1,4-pentanediamine
Mepacrinum (INN-Latin)
Mepacrina (INN-Spanish)
6-CHLORO-N-[5-(DIETHYLAMINO)PENTAN-2-YL]-2-METHOXYACRIDIN-9-AMINE
N(4)-(6-chloro-2-methoxy-9-acridinyl)-N(1),N(1)-diethyl-1,4-pentanediamine
Atabrine hydrochloride dihydrate; Mepacrine hydrochloride
6-chloro-N-(5-(diethylamino)pentan-2-yl)-2-methoxyacridin-9-amine
N'-(6-chloro-2-methoxyacridin-9-yl)-N,N-diethylpentane-1,4-diamine
Quinacrine, Mepacrine
UNII-H0C805XYDE
Acirchine
Acridine, 6-chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]-2-methoxy-
N~4~-(6-chloro-2-methoxyacridin-9-yl)-N~1~,N~1~-diethylpentane-1,4-diamine
Quinacrine,Mepacrine
ACRINAMIONE
Atebrin (Salt/Mix)
Atebrine (Salt/Mix)
Spectrum_000929
Prestwick0_000318
Prestwick1_000318
Prestwick2_000318
Prestwick3_000318
Spectrum2_000888
Spectrum3_000606
Spectrum4_000496
Spectrum5_001405
(.+/-.)-Quinacrine
Lopac0_000970
SCHEMBL19225
BSPBio_000316
BSPBio_002112
KBioGR_001011
KBioGR_002507
KBioSS_001409
KBioSS_002515
DivK1c_000101
SPBio_000676
SPBio_002535
BPBio1_000348
DTXCID802627
GTPL10172
KBio1_000101
KBio2_001409
KBio2_002507
KBio2_003977
KBio2_005075
KBio2_006545
KBio2_007643
KBio3_001612
KBio3_002985
P01AX05
cMAP_000067
NINDS_000101
acrichinum (for the hydrochloride)
HMS2090L03
BBL028456
BDBM50015214
RP-866 (Dihydrochloride dihydrate)
SN-390 (Dihydrochloride dihydrate)
STL061087
AKOS000541535
AKOS016340229
CCG-205050
DB01103
MS-1557
SDCCGSBI-0050943.P006
IDI1_000101
N*4*-(6-Chloro-2-methoxy-acridin-9-yl)-N*1*,N*1*-diethyl-pentane-1,4-diamine
NCGC00015874-02
NCGC00015874-03
NCGC00015874-04
NCGC00015874-06
NCGC00015874-08
NCGC00015874-12
NCGC00162300-01
DA-67071
HY-13735
NCI60_000926
SBI-0050943.P004
AB00053540
CS-0007762
NS00003697
C07339
D08179
EN300-246511
G78134
AB00053540-08
AB00053540-09
AB00053540_10
Q417208
BRD-A45889380-300-04-8
BRD-A45889380-300-06-3
BRD-A45889380-300-07-1
BRD-A45889380-300-08-9
BRD-A45889380-336-03-4
Z31251611
2-Methoxy-6-chloro-9-diethylaminopent-2-ylaminoacridine
6-chloro-2-methoxy-9-acridinyl(4-diethylamino-1-methylbutyl)amine
acridine, 3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)-
acridine, 3-chloro-9-(4-diethylamino-1-methyl)butylamino-7-methoxy-
N''-(6-chloro-2-methoxy-acridin-9-yl)-N,N-diethyl-pentane-1,4-diamine
N4-(6-chloro-2-methoxy-acridin-9-yl)-N1,N1-diethyl-pentane-1,4-diamine
N4-(6-chloro-2-methoxyacridin-9-yl)-N1,N1-diethylpentane-1,4-diamine
1,4-PENTANEDIAMINE, N(4)-(6-CHLORO-2-METHOXY-9-ACRIDINYL)-N(1),N(1)-DIETHYL-
6-CHLORO-9-((4-(DIMETHYLAMINO)-1-METHYLBUTYL)AMINO)-2-METHOXYACRIDINE
N'-(6-Chloro-2-methoxy-acridin-9-yl)-N,N-diethyl-pentane-1,4-diamine dihydrochloride
N*4*-(6-Chloro-2-methoxy-acridin-9-yl)-N*1*,N*1*-diethyl-pentane-1,4-diamine (Mepacrine)
N~4~-[6-chloro-2-(methyloxy)acridin-9-yl]-N~1~,N~1~-diethylpentane-1,4-diamine
201-508-7
N*4*-(6-Chloro-2-methoxy-acridin-9-yl)-N*1*,N*1*-diethyl-pentane-1,4-diamine ; (mepacrine)