1-(Trideuteriomethyl)piperazine
Overview
Description
1-(Trideuteriomethyl)piperazine is a deuterated derivative of piperazine, a heterocyclic organic compound The deuterium atoms replace the hydrogen atoms in the methyl group, which can influence the compound’s physical and chemical properties
Scientific Research Applications
1-(Trideuteriomethyl)piperazine has a wide range of applications in scientific research:
Chemistry: It is used as a building block in the synthesis of complex molecules and as a deuterated standard in NMR spectroscopy.
Biology: The compound is utilized in studies involving metabolic pathways and enzyme mechanisms.
Medicine: It has potential therapeutic applications due to its stability and unique isotopic properties.
Industry: The compound is used in the development of new materials and as a tracer in various industrial processes.
Safety and Hazards
Mechanism of Action
Target of Action
1-(Trideuteriomethyl)piperazine, also known as 1-(METHYL-D3)PIPERAZINE, is a derivative of piperazine . Piperazine compounds are known to target the GABA receptors . They bind directly and selectively to muscle membrane GABA receptors . Piperazine is also involved in the 5-HT1AR/BDNF/PKA pathway .
Mode of Action
The interaction of this compound with its targets results in specific changes. For instance, when piperazine binds to the GABA receptors, it presumably causes hyperpolarization of nerve endings, resulting in flaccid paralysis of the worm . This is how piperazine compounds mediate their anthelmintic action .
Biochemical Pathways
This compound affects the GABAergic pathway and the 5-HT1AR/BDNF/PKA pathway . The GABAergic pathway is involved in inhibitory neurotransmission in the central nervous system. The 5-HT1AR/BDNF/PKA pathway is associated with antidepressant activity .
Pharmacokinetics
Upon entry into the systemic circulation, piperazine, a related compound, is partly oxidized and partly eliminated as an unchanged compound . More research is needed to understand the ADME properties of this compound.
Result of Action
The result of the action of this compound depends on its targets. For instance, the anthelmintic action of piperazine results in the paralysis and expulsion of parasites . In the context of the 5-HT1AR/BDNF/PKA pathway, piperazine derivatives may have potential antidepressant activity .
Biochemical Analysis
Biochemical Properties
1-(Trideuteriomethyl)piperazine plays a significant role in biochemical reactions. It interacts with various enzymes, proteins, and other biomolecules. For instance, it has been found to inhibit the activity of certain efflux pumps in bacteria, thereby increasing the sensitivity of these organisms to antibiotics . The nature of these interactions is largely dependent on the specific biochemical context in which this compound is present .
Cellular Effects
The effects of this compound on various types of cells and cellular processes are diverse. It influences cell function by impacting cell signaling pathways, gene expression, and cellular metabolism . For example, it has been shown to have significant effects on the function of immune cells .
Molecular Mechanism
The mechanism of action of this compound involves complex interactions at the molecular level. It binds to specific biomolecules, inhibits or activates enzymes, and induces changes in gene expression . These actions contribute to its overall effects on cellular and physiological processes.
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound can change over time. This includes information on the product’s stability, degradation, and any long-term effects on cellular function observed in in vitro or in vivo studies .
Dosage Effects in Animal Models
The effects of this compound vary with different dosages in animal models. At therapeutic doses, it is generally well-tolerated, but at higher doses, it can cause neurotoxic symptoms .
Metabolic Pathways
This compound is involved in various metabolic pathways. It interacts with enzymes and cofactors, and can affect metabolic flux or metabolite levels .
Transport and Distribution
This compound is transported and distributed within cells and tissues. It interacts with transporters or binding proteins, and can affect its localization or accumulation .
Subcellular Localization
It could include any targeting signals or post-translational modifications that direct it to specific compartments or organelles .
Preparation Methods
Synthetic Routes and Reaction Conditions: 1-(Trideuteriomethyl)piperazine can be synthesized through various methods. One common approach involves the deuteration of 1-methylpiperazine using deuterium gas or deuterated reagents. The reaction typically requires a catalyst and specific conditions to ensure the incorporation of deuterium atoms.
Industrial Production Methods: Industrial production of this compound often involves large-scale deuteration processes. These processes are optimized for high yield and purity, utilizing advanced catalytic systems and controlled reaction environments to achieve the desired isotopic substitution.
Chemical Reactions Analysis
Types of Reactions: 1-(Trideuteriomethyl)piperazine undergoes various chemical reactions, including:
Oxidation: The compound can be oxidized to form corresponding N-oxides.
Reduction: Reduction reactions can lead to the formation of deuterated amines.
Substitution: Nucleophilic substitution reactions can occur at the nitrogen atoms or the deuterated methyl group.
Common Reagents and Conditions:
Oxidation: Common oxidizing agents include hydrogen peroxide and peracids.
Reduction: Reducing agents such as lithium aluminum hydride or sodium borohydride are used.
Substitution: Halogenated compounds and strong bases are often employed in substitution reactions.
Major Products: The major products formed from these reactions depend on the specific reagents and conditions used. For example, oxidation can yield N-oxides, while reduction can produce deuterated amines.
Comparison with Similar Compounds
1-(Trideuteriomethyl)piperazine can be compared with other deuterated piperazine derivatives and non-deuterated analogs:
Similar Compounds: 1-methylpiperazine, 1-(trideuteriomethyl)piperidine, and 1-(trideuteriomethyl)morpholine.
Uniqueness: The presence of deuterium atoms in this compound provides enhanced stability and altered metabolic pathways compared to its non-deuterated counterparts. This makes it particularly useful in applications requiring precise isotopic labeling and stability.
Properties
IUPAC Name |
1-(trideuteriomethyl)piperazine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C5H12N2/c1-7-4-2-6-3-5-7/h6H,2-5H2,1H3/i1D3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
PVOAHINGSUIXLS-FIBGUPNXSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CN1CCNCC1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
[2H]C([2H])([2H])N1CCNCC1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C5H12N2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Weight |
103.18 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Synthesis routes and methods I
Procedure details
Synthesis routes and methods II
Procedure details
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
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