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Amsacrine

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Identification
Molecular formula
C21H19N3O3S
CAS number
51264-14-3
IUPAC name
N-[4-(acridin-9-ylamino)-3-methoxy-phenyl]methanesulfonamide
State
State

At room temperature, Amsacrine is typically in a solid state.

Melting point (Celsius)
164.00
Melting point (Kelvin)
437.10
Boiling point (Celsius)
311.20
Boiling point (Kelvin)
584.30
General information
Molecular weight
393.46g/mol
Molar mass
393.4610g/mol
Density
1.3400g/cm3
Appearence

Amsacrine is typically found as a light-yellow solid. It can appear as a powder or crystalline substance, depending on its specific form or preparation. The compound may undergo changes in appearance when exposed to light, as it is known to be photoreactive.

Comment on solubility

Solubility of N-[4-(acridin-9-ylamino)-3-methoxy-phenyl]methanesulfonamide

The solubility of N-[4-(acridin-9-ylamino)-3-methoxy-phenyl]methanesulfonamide (C21H19N3O3S) varies significantly depending on the solvent used and the conditions applied. Generally, this compound can be considered to have the following solubility characteristics:

  • Water Solubility: This compound is likely to exhibit limited solubility in water due to its large hydrophobic aromatic structure.
  • Organic Solvents: It may dissolve more readily in organic solvents such as ethanol, DMSO (dimethyl sulfoxide), or acetone owing to the non-polar interactions.
  • pH Dependency: The solubility might also be influenced by the pH of the solution, particularly if any protonation or deprotonation reactions occur at specific pH levels.

It is essential to conduct solubility tests under controlled conditions to determine the exact solubility profile of this compound. Factors such as temperature and the presence of co-solvents can also impact its solubility behavior. Remember, the phrase “solubility is key” can often dictate the application and efficacy of compounds in various chemical and biological systems.

Interesting facts

Interesting Facts about N-[4-(Acridin-9-ylamino)-3-methoxy-phenyl]methanesulfonamide

N-[4-(Acridin-9-ylamino)-3-methoxy-phenyl]methanesulfonamide is an intriguing compound that has garnered attention in the field of medicinal chemistry. Here are some noteworthy facts:

  • Versatile Applications: This compound possesses properties that make it a potential candidate for pharmaceutical applications, particularly in the realm of cancer research and treatment due to its unique molecular structure.
  • Mechanism of Action: The acridine moiety in the compound is reminiscent of many DNA-acting drugs. These types of compounds can intercalate into DNA, which may lead to an inhibition of cancer cell growth.
  • Sulfonamide Feature: The presence of the sulfonamide group enhances the compound's solubility and can improve its pharmacokinetic properties, making it easier for the drug to reach its targets in the body.
  • Research Interest: Studies on this compound are still ongoing, as researchers are keen to explore its efficacy and mechanism. As highlighted by one researcher: "Compounds like this hold the key to unlocking new cancer therapies."
  • Pioneering Structure: The combination of acridine and methanesulfonamide provides a framework for further modifications, thereby enabling the development of more potent derivatives useful in various medical fields.

In summary, N-[4-(Acridin-9-ylamino)-3-methoxy-phenyl]methanesulfonamide represents a significant topic of study in drug design and development. Its unique structural characteristics and potential applications in targeting cancer cells stand as a testament to the innovative nature of modern chemistry.

Synonyms
amsacrine
51264-14-3
Amsidine
m-AMSA
Amsidyl
Acridinylanisidide
Amsacrina
Lamasine
Amekrin
mAMSA
Amsacrinum
Acridinyl Anisidide
meta-Amsacrine
amsidil
Amsine
4'-(9-Acridinylamino)methanesulfon-m-anisidide
AMSA
Amsacrinum [INN-Latin]
Amsacrina [INN-Spanish]
SN-11841
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilide
NSC-249992
N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide
4'-(9-Acridinylamino)methanesulphon-m-anisidide
CI-880
NSC249992
NSC 156303
NSC 249992
NSC-156303
Methanesulfonamide, N-[4-(9-acridinylamino)-3-methoxyphenyl]-
Amsidyl (TN)
SN 21429
4'-(9-Acridinylamino)methanesulfon-meta-anisidide
N-(4-(Acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide
CCRIS 1027
HSDB 7087
m-AMSA;acridinyl anisidide
EINECS 257-094-3
00DPD30SOY
CI 880
Amsacrine [USAN:INN:BAN]
N-(4-(9-Acridinylamino)-3-methoxyphenyl)methanesulfonamide
N-[4-(9-Acridinylamino)-3-methoxyphenyl]methanesulfonamide
BRN 0500176
CHEBI:2687
Methanesulfonamide, N-(4-(9-acridinylamino)-3-methoxyphenyl)-
AMSACRINE [INN]
AMSACRINE [MI]
Methanesulfonanilide, 4'-(9-acridinylamino)-3'-methoxy-
AMSACRINE [HSDB]
AMSACRINE [IARC]
AMSACRINE [USAN]
CHEMBL43
AMSACRINE [VANDF]
AMSACRINE [MART.]
NCI-249992
AMSACRINE [WHO-DD]
Methanesulfon-m-anisidide, 4'-(9-acridinylamino)-
SN-21429
DTXSID4022604
Cain's Acridine
5-22-11-00030 (Beilstein Handbook Reference)
meta-AMSA
AMSA P-D
AMSACRINE (IARC)
Amsacrinum (INN-Latin)
N-[4-(acridin-9-ylamino)-3-(methyloxy)phenyl]methanesulfonamide
Amsacrina (INN-Spanish)
N-{4-[(ACRIDIN-9-YL)AMINO]-3-METHOXYPHENYL}METHANESULFONAMIDE
NSC156303
AMSACRINE (MART.)
C21H19N3O3S
m-AMSA hydrochloride; acridinyl anisidide hydrochloride
Amecrin
Cains Acridine
Cain Acridine
MLS002153376
meta AMSA
nAMSA
SN11841
AMSA PD
Amsacrine (USAN/INN)
AMSA P D
SMR000875352
UNII-00DPD30SOY
AMSA, M-
N-(4-((acridin-9-yl)amino)-3-methoxyphenyl)methanesulfonamide
ASW
MFCD00242748
Amsacrine (Standard)
Lopac-A-9809
NCIMech_000607
Neuro_000118
SCHEMBL4047
Lopac0_000154
MLS006010099
cid_148673
DTXCID002604
BDBM87351
HMS3748E05
N-[4-(9-Acridinylamino)-3-methoxy-phenyl]methanesulfonamide
BCP08958
CCG-35555
HY-13551R
AKOS015917522
CS-1942
DB00276
SDCCGSBI-0050142.P003
NCGC00015113-01
NCGC00015113-02
NCGC00015113-03
NCGC00015113-04
NCGC00093644-07
NCGC00093644-10
NCGC00162077-01
AS-11665
DA-50187
HY-13551
NCI60_001995
SMR000857391
WLN: T C666 BNJ IMR BO1 DMSW1
DB-082052
NS00008525
C01553
C75400
D02321
4'-(9-Acridinylamino)methane-sulfon-m-anisidide
4'-(9-Acridinylamino)methanesulfonyl m-anisidide
EN300-7481264
4'-(9-Acridinylamino)-methylsulfonyl-m-anisidine
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanlide
Q2784004
BRD-K68346641-001-01-4
BRD-K68346641-001-02-2
Methanesulfonanilide,4'-(9-acridinylamino)-3'methoxy-
N-[4-(9-acridinylamino)-3-methoxyphenyl]methanesulfonamide;hydrochloride
N-[4-(acridin-9-ylamino)-3-methoxy-phenyl]methanesulfonamide;hydrochloride
257-094-3