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Cocaine

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Identification
Molecular formula
C17H21NO4
CAS number
50-36-2
IUPAC name
ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
State
State

At room temperature, cocaine is typically found as a solid in the form of a fine powder or crystalline flakes. The state can vary between its salt form (hydrochloride) and its base form ('crack cocaine') depending on the region and intended use. It is highly soluble in water, especially in its hydrochloride form.

Melting point (Celsius)
98.00
Melting point (Kelvin)
371.15
Boiling point (Celsius)
187.00
Boiling point (Kelvin)
460.15
General information
Molecular weight
303.35g/mol
Molar mass
303.3530g/mol
Density
1.2200g/cm3
Appearence

Cocaine is generally found as a white crystalline powder, which is the hydrochloride salt form. It may also appear as shiny, white flakes or rocks when in its base form. This compound can sometimes have a pearly or gloss-like appearance, depending on its purity and processing method.

Comment on solubility

Solubility of Ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

The solubility of a compound can significantly influence its applications and behavior in various environments. In the case of ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (C17H21NO4), several factors come into play:

  • Polarity: This compound features both hydrophobic and hydrophilic regions, stemming from its complex structure which includes the benzoyloxy group and the hydrophilic carboxylate. As a result, it may exhibit variable solubility in different solvents.
  • Solvent Interaction: It is likely to be soluble in organic solvents such as ethanol, chloroform, and dimethyl sulfoxide (DMSO) due to its non-polar characteristics. However, its solubility in water is expected to be limited.
  • pH Influence: The solubility might also depend on the pH of the solution. In acidic conditions, the carboxylate group can become protonated, affecting the solubility profile.

Understanding the solubility of ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate is essential for its application in pharmaceuticals and materials science, making it a pivotal aspect of research related to this compound.

Interesting facts

Interesting Facts about Ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate presents an intriguing example of organic synthesis and drug design. Here are several fascinating aspects of this compound:

  • Structural Complexity: The bicyclic structure of this molecule allows for unique conformational characteristics that may affect its reactivity and interactions with biological systems.
  • Potential Pharmacological Relevance: Compounds resembling this structure are often investigated for their effects on the central nervous system, potentially leading to new therapeutic agents.
  • Functionality: The presence of a benzoyloxy group is indicative of its potential reactivity, which can be exploited in further synthetic transformations.
  • Chirality: The compound likely features chirality at several positions, highlighting the significance of stereochemistry in the design of effective pharmaceuticals.
  • Synthetic Pathways: This compound could be synthesized via several methodologies, including multi-step organic synthesis or utilizing specific reagents for functional group modifications.

As noted by chemist Dr. Emily Carter, "The complexity within organic compounds often leads to unexpected biological activities, making them a treasure trove for medicinal chemistry." The exploration of compounds like ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate emphasizes the importance of interdisciplinary research, merging synthetic organic chemistry with biological applications.

This compound's intricate design not only showcases the artistry of organic synthesis but also opens doors to potential advancements in drug discovery and development.

Synonyms
Ethylbenzoylecgonine
Homocaine
CHEMBL127457
(-)-Cocaethylene fumarate
MLS002320699
[1R-(Exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylateacid
SMR001338845
Benzoyl Ecgonine Ethyl Ester-d8
DivK1c_000974
BDBM94624
HMS503C09
KBio1_000974
3-Benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid ethyl ester
CHEBI:182818
cid_45479832
NINDS_000974
NMPOSNRHZIWLLL-UHFFFAOYSA-N
Thylbenzoylecgonine (cocaethylene)
CGA52109
BDBM50035782
IDI1_000974
DB-052216
Ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate #
ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
(E)-but-2-enedioate;ethyl 3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate
3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid ethyl ester;fumarate
(E)-but-2-enedioate;ethyl 8-methyl-3-(phenylcarbonyloxy)-8-azabicyclo[3.2.1]octane-4-carboxylate
3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid ethyl ester;(E)-2-butenedioate