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Chlorpromazine

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Identification
Molecular formula
C17H19ClN2OS
CAS number
50-53-3
IUPAC name
8-chloro-10-[3-(dimethylamino)propyl]phenothiazin-4-ol
State
State

At room temperature, chlorpromazine exists as a solid.

Melting point (Celsius)
196.00
Melting point (Kelvin)
469.15
Boiling point (Celsius)
406.00
Boiling point (Kelvin)
679.15
General information
Molecular weight
318.85g/mol
Molar mass
318.8530g/mol
Density
1.3010g/cm3
Appearence

Chlorpromazine appears as a white to off-white crystalline powder. It may have a slight odor and is slightly soluble in water, but more soluble in chloroform and alcohol.

Comment on solubility

Solubility of 8-chloro-10-[3-(dimethylamino)propyl]phenothiazin-4-ol

The solubility of 8-chloro-10-[3-(dimethylamino)propyl]phenothiazin-4-ol in various solvents can be quite informative in understanding its behavior in chemical environments. This compound exhibits notable characteristics:

  • Moderate Solubility in Organic Solvents: It tends to dissolve well in organic solvents such as ethanol and dimethyl sulfoxide (DMSO) due to its nonpolar and polar functional groups.
  • Limited Solubility in Water: As a phenothiazine derivative, it shows poor solubility in water, which can be attributed to its hydrophobic aromatic structure combined with the presence of the chloro group.
  • Influence of pH: The solubility may increase in acidic environments, where protonation could enhance its interaction with the solvent.

In practical terms, this compound's solubility profile is crucial for its application in pharmaceuticals, affecting factors such as bioavailability and formulation strategies. As with many chemical compounds, solubility is a key determinant of how well the substance can be delivered and utilized in biological systems.

Interesting facts

Interesting Facts about 8-Chloro-10-[3-(dimethylamino)propyl]phenothiazin-4-ol

8-Chloro-10-[3-(dimethylamino)propyl]phenothiazin-4-ol, often recognized for its complex structure, holds significance in both medicinal chemistry and psychopharmacology. This compound belongs to the phenothiazine family, which is an established class of pharmaceuticals that have been widely used since the mid-20th century.

  • Medicinal Uses: The derivative of this compound is primarily employed as an antipsychotic medication. It is believed to influence neurotransmitter activity in the brain, particularly dopamine receptors, which plays a crucial role in alleviating symptoms of schizophrenia and other mental health disorders.

  • Research Interests: Research has shown that phenothiazines, including this compound, exhibit a range of pharmacological activities. These include antihistaminic, antiemetic, and even antimicrobial properties, making them a versatile topic of study.

  • Structure-Activity Relationship: The presence of the dimethylamino group and the chloro substituent is believed to enhance the compound's binding affinity to biological targets, leading to improved therapeutic effects. This opens avenues for the synthesis of new derivatives with potentially enhanced or reduced side effects.

  • Historical Context: The origins of phenothiazine derivatives date back to the discovery of the first antipsychotic agent, chlorpromazine in the 1950s, which revolutionized mental health treatment. Compounds like this one are pivotal in understanding the development of neurotransmitter-modulating agents.

In summary, 8-Chloro-10-[3-(dimethylamino)propyl]phenothiazin-4-ol is not just a compound with a complex name; it embodies the evolution of pharmacotherapy for mental health and continues to be a subject of interest in ongoing research aimed at optimizing medicinal efficacy through chemical modification.

Synonyms
6-Hydroxychlorpromazine
3926-65-6
PHENOTHIAZINE, 2-CHLORO-10-(3-(DIMETHYLAMINO)PROPYL)-6-HYDROXY-
2-Chloro-6-hydroxy-10-(3-(dimethylamino)propyl)phenothiazine
10H-Phenothiazin-4-ol, 8-chloro-10-(3-(dimethylamino)propyl)-
10H-Phenothiazin-4-ol, 8-chloro-10-[3-(dimethylamino)propyl]-
BRN 1023717
8-chloro-10-[3-(dimethylamino)propyl]phenothiazin-4-ol
DTXSID30192508
SGVAWVKNKIMXPP-UHFFFAOYSA-N
Phenothiazin-4-ol, 8-chloro-10-[3-(dimethylamino)propyl]-
8-Chloro-10-[3-(dimethylamino)propyl]-10H-phenothiazin-4-ol #