(+/-)-exo-6-Hydroxytropinone
[CAS# 5932-53-6]

Identification

• Classification: Biochemical >> Plant extracts
• Name: (+/-)-exo-6-Hydroxytropinone
• Synonyms: 6-Hydroxy-8-methylazabicyclo[3.2.1]octan-3-one
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.19
• CAS Registry Number: 5932-53-6
• EC Number: 227-677-7
• SMILES: CN1[C@@H]2C[C@@H]([C@H]1CC(=O)C2)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 120-123 ºC (Expl.)
• Index of Refraction: 1.545, Calc.^*
• Boiling Point: 291.6±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 130.1±25.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(+/-)-exo-6-Hydroxytropinone is a chemical compound that has garnered attention in the field of organic chemistry due to its unique structure and potential applications in various chemical processes. It is a member of the tropinone family, which is known for its involvement in the biosynthesis of alkaloids, particularly tropane alkaloids, which have a variety of biological effects. The compound is characterized by its hydroxyl group at the 6-position on the tropinone ring, a feature that imparts certain chemical reactivity and biological activity.

The discovery of (+/-)-exo-6-hydroxytropinone can be traced back to research focused on the tropane ring system, which has been extensively studied for its role in medicinal chemistry. The tropane structure is central to many naturally occurring compounds, including well-known drugs like atropine and scopolamine, which are derived from plants in the Solanaceae family. These compounds are used in a variety of medical applications, from treating motion sickness to acting as antidotes for nerve agent poisoning. The introduction of a hydroxyl group at the 6-position in the tropinone structure was likely an intentional modification to explore how this change could impact the compound’s biological activity and potential therapeutic uses.

The chemical synthesis of (+/-)-exo-6-hydroxytropinone involves complex organic reactions, including the reduction of key intermediates and the introduction of functional groups such as the hydroxyl group. This process often requires precise control of reaction conditions to ensure the correct stereochemistry and high yield. The racemic nature of (+/-)-exo-6-hydroxytropinone indicates that both enantiomers of the compound are produced in the synthesis, which has implications for its biological activity and pharmacological profile.

One of the most significant applications of (+/-)-exo-6-hydroxytropinone is in the synthesis of other tropane-based compounds. As a versatile intermediate, it serves as a building block for the preparation of various tropane alkaloids, which are of interest in the pharmaceutical industry. Tropane alkaloids are known for their diverse range of effects on the central nervous system, including their use as anticholinergic agents and their involvement in the modulation of neurotransmitter systems. For example, compounds derived from tropinone, such as atropine and scopolamine, are widely used in clinical settings to treat conditions such as bradycardia, motion sickness, and Parkinson’s disease.

The hydroxylation at the 6-position of (+/-)-exo-6-hydroxytropinone can also influence its interaction with enzymes involved in the synthesis or degradation of neurotransmitters, potentially altering its pharmacological properties. This modification may enhance or diminish the activity of the resulting compounds, depending on the specific biological target. Therefore, (+/-)-exo-6-hydroxytropinone has been of interest for its potential role in the development of new therapeutic agents, particularly those aimed at treating central nervous system disorders.

In addition to its pharmaceutical applications, (+/-)-exo-6-hydroxytropinone is also studied for its use in synthetic chemistry as a precursor for more complex organic molecules. Its structural features, particularly the tropane ring system, make it a valuable intermediate in the synthesis of a variety of other biologically active compounds. The introduction of the hydroxyl group at the 6-position can be used as a handle for further functionalization, leading to the creation of a range of novel molecules with potential biological activity.

The application of (+/-)-exo-6-hydroxytropinone extends beyond its role in drug synthesis and development. It is also used in the development of chemical processes for the synthesis of other complex organic molecules. The tropane skeleton is highly versatile, and compounds based on this structure can be modified in numerous ways to create new molecules with varying degrees of biological activity. In this way, (+/-)-exo-6-hydroxytropinone contributes to the broader field of synthetic organic chemistry, aiding in the discovery of new compounds with a wide range of applications.

Despite its potential, the use of (+/-)-exo-6-hydroxytropinone in the pharmaceutical industry requires further research to fully understand its pharmacokinetic and pharmacodynamic properties. Its racemic mixture may exhibit different effects depending on the specific enantiomer, and additional studies are needed to isolate and evaluate the individual enantiomers for their therapeutic potential. Moreover, the safety and toxicity profiles of compounds derived from (+/-)-exo-6-hydroxytropinone must be thoroughly assessed to ensure their suitability for clinical use.

In conclusion, (+/-)-exo-6-hydroxytropinone is a significant chemical compound with promising applications in both pharmaceutical and synthetic chemistry. Its role as an intermediate in the synthesis of tropane alkaloids and other biologically active compounds makes it an important molecule in drug development. Ongoing research into its properties and potential applications will likely lead to the discovery of new therapeutic agents and broaden its utility in the field of medicinal chemistry.