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Lysergic acid diethylamide

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Identification
Molecular formula
C20H25N3O
CAS number
50-37-3
IUPAC name
(4S,4aS,7S,12bS)-3-(cyclobutylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
State
State

In its pure form, at room temperature, it is a solid. It is commonly found as small tablets, capsules, or gelatin squares when used in various applications. Despite its solid state, it is soluble in water and other solvents.

Melting point (Celsius)
82.00
Melting point (Kelvin)
355.15
Boiling point (Celsius)
105.00
Boiling point (Kelvin)
378.15
General information
Molecular weight
323.41g/mol
Molar mass
323.4080g/mol
Density
1.2300g/cm3
Appearence

This compound typically appears as a white or off-white crystalline substance. The crystals are fine and often have a slight sheen. It is known for being light-sensitive and can degrade under exposure to light, resulting in a gradual yellowing.

Comment on solubility

Solubility of (4S,4aS,7S,12bS)-3-(cyclobutylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol

The solubility of this complex organic compound can be characterized by several important factors:

  • Polarity: The presence of multiple hydroxyl groups (–OH) in its structure typically enhances solubility in polar solvents, such as water.
  • Hydrophobic Character: The cyclobutylmethyl portion introduces a hydrophobic component, which can limit solubility in more polar environments.
  • Intermolecular Interactions: Hydrogen bonding capabilities with water molecules can increase solubility, but the overall steric hindrance may also impede it.

Due to these contrasting effects, the solubility profile of this compound can be summarized as follows:

  1. If tested in water, solubility may be moderate owing to the balance between the polar –OH groups and the non-polar cyclobutylmethyl side chain.
  2. In organic solvents like ethanol or dimethyl sulfoxide (DMSO), it is likely to show improved solubility.
  3. It's essential to consider the specific conditions, such as temperature and pH, which can further influence solubility.

In conclusion, the solubility of this compound is expected to be influenced significantly by its molecular structure and the nature of the solvent used, making it crucial for practical applications to determine its solubility profile under various conditions.

Interesting facts

Interesting Facts about (4S,4aS,7S,12bS)-3-(cyclobutylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol

This fascinating compound, with its intricate structure, belongs to a family of isoquinoline derivatives known for their diverse biological activities. Here are some intriguing insights into this chemical:

  • Complex Structure: The naming of this compound reflects its complicated molecular architecture, showcasing a blend of cyclic and polycyclic systems.
  • Potential Biological Activity: Isoquinoline derivatives are frequently studied for their therapeutic potentials and can exhibit significant pharmacological properties, including anti-inflammatory, analgesic, and anti-cancer activities.
  • Cyclobutylmethyl Group: The presence of the cyclobutylmethyl moiety contributes to its unique interactions in biological systems, impacting its efficacy as a potential drug candidate.
  • Chirality: The compound features several chiral centers, which may influence its behavior in biological systems, as chirality is a key factor in drug interactions.
  • Research Frontier: Continuous research involving such complex compounds is crucial to unlocking their full potential, making them appealing subjects for chemists and biochemists alike.

As a student or scientist delving into the world of organic chemistry, understanding compounds like this one can provide insights into the fundamental principles of molecular interactions and the development of new therapeutic agents. It underscores the importance of structure-activity relationships in designing more effective drugs.

In conclusion, this compound not only embodies the complexity of synthetic organic chemistry but also represents the endless possibilities for innovation in medicinal chemistry.