3-(methylamino)-1-phenylpropan-1-ol
Vue d'ensemble
Description
Mécanisme D'action
Mode of Action
It is mentioned that this compound is an aromatic amino alcohol used as an initiator in radical addition reactions with tetrahalomethanes . This suggests that it may interact with its targets by initiating radical addition reactions, leading to changes in the targets’ structure or function .
Biochemical Pathways
Given its role as an initiator in radical addition reactions, it may influence pathways involving these reactions .
Pharmacokinetics
Some physical and chemical properties of the compound are provided . It has a melting point of 64 °C, a boiling point of 170 °C at 31mmHg, and a density of 1.017±0.06 g/cm3 (Predicted) . It is soluble in DMSO and slightly soluble in methanol . These properties may influence its bioavailability and pharmacokinetics.
Result of Action
Given its role as an initiator in radical addition reactions, it may cause changes in the structure or function of its targets .
Analyse Biochimique
Biochemical Properties
3-Hydroxy-N-methyl-3-phenyl-propylamine plays a significant role in biochemical reactions, particularly as an initiator in radical addition reactions. It interacts with enzymes and proteins involved in these reactions, facilitating the formation of new chemical bonds. The compound’s interaction with tetrahalomethanes is particularly noteworthy, as it helps in the formation of stable radicals that can further react with other biomolecules . Additionally, 3-Hydroxy-N-methyl-3-phenyl-propylamine is known to interact with various amino acids and their derivatives, influencing their biochemical pathways .
Cellular Effects
The effects of 3-Hydroxy-N-methyl-3-phenyl-propylamine on cellular processes are diverse. It has been observed to influence cell signaling pathways, gene expression, and cellular metabolism. The compound can modulate the activity of certain enzymes, leading to changes in metabolic flux and the levels of various metabolites . In particular, its interaction with amino acids and their derivatives can lead to alterations in protein synthesis and degradation, impacting overall cellular function .
Molecular Mechanism
At the molecular level, 3-Hydroxy-N-methyl-3-phenyl-propylamine exerts its effects through binding interactions with biomolecules. It can act as an enzyme inhibitor or activator, depending on the specific biochemical context. The compound’s ability to form stable radicals allows it to participate in radical addition reactions, which can lead to changes in gene expression and enzyme activity . These interactions are crucial for understanding the compound’s role in various biochemical pathways.
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of 3-Hydroxy-N-methyl-3-phenyl-propylamine have been studied over time to understand its stability and degradation. The compound is relatively stable under standard laboratory conditions, but it can degrade over time when exposed to light and air . Long-term studies have shown that the compound can have lasting effects on cellular function, particularly in terms of enzyme activity and metabolic flux .
Dosage Effects in Animal Models
The effects of 3-Hydroxy-N-methyl-3-phenyl-propylamine vary with different dosages in animal models. At low doses, the compound can enhance certain biochemical pathways, leading to beneficial effects on cellular function . At high doses, it can have toxic or adverse effects, including enzyme inhibition and disruption of metabolic processes . These dosage-dependent effects are crucial for understanding the compound’s potential therapeutic applications and risks.
Metabolic Pathways
3-Hydroxy-N-methyl-3-phenyl-propylamine is involved in several metabolic pathways, interacting with enzymes and cofactors that facilitate its conversion into various metabolites. The compound’s interaction with amino acids and their derivatives is particularly important, as it can influence protein synthesis and degradation . Additionally, the compound can affect metabolic flux, leading to changes in the levels of various metabolites .
Transport and Distribution
Within cells and tissues, 3-Hydroxy-N-methyl-3-phenyl-propylamine is transported and distributed through interactions with specific transporters and binding proteins. These interactions help in the localization and accumulation of the compound in specific cellular compartments . The compound’s distribution is crucial for its biochemical activity, as it needs to reach specific sites within the cell to exert its effects .
Subcellular Localization
The subcellular localization of 3-Hydroxy-N-methyl-3-phenyl-propylamine is influenced by targeting signals and post-translational modifications that direct it to specific compartments or organelles. The compound is often found in the cytoplasm, where it interacts with various enzymes and proteins involved in metabolic pathways . Its localization is crucial for its activity, as it needs to be in the right place at the right time to exert its biochemical effects .
Méthodes De Préparation
The synthesis of 3-(methylamino)-1-phenylpropan-1-ol can be achieved through several methods :
Reduction of Propiophenone Derivatives: Starting with halogenated propiophenone derivatives, reduction followed by conversion to this compound.
Reductive Ring Opening of Isoxazolidines: Using 2-methyl-5-phenylisoxazolidine as a precursor, reductive ring opening yields the target compound.
Epoxide Opening: Epoxy styrene derivatives can be reduced to form the desired product.
Analyse Des Réactions Chimiques
3-(methylamino)-1-phenylpropan-1-ol undergoes various chemical reactions :
Oxidation: This compound can be oxidized to form corresponding ketones or aldehydes.
Reduction: It can be reduced to form secondary or tertiary amines.
Substitution: The hydroxyl group can be substituted with other functional groups using appropriate reagents.
Common Reagents and Conditions: Typical reagents include oxidizing agents like potassium permanganate, reducing agents like lithium aluminum hydride, and substitution reagents like thionyl chloride.
Applications De Recherche Scientifique
3-(methylamino)-1-phenylpropan-1-ol has several applications in scientific research :
Chemistry: It is used as an initiator in radical addition reactions with tetrahalomethanes.
Biology: It serves as an intermediate in the synthesis of biologically active compounds.
Medicine: It is a key intermediate in the production of fluoxetine hydrochloride, a widely used antidepressant.
Industry: It is used in the synthesis of various fine chemicals and pharmaceuticals.
Comparaison Avec Des Composés Similaires
3-(methylamino)-1-phenylpropan-1-ol can be compared with other similar compounds :
3-Phenylpropanamine: Similar structure but lacks the hydroxyl group.
Benzenepropanamine: Similar structure but lacks the methyl and hydroxyl groups.
Gamma-phenylpropylamine: Similar structure but lacks the hydroxyl group.
Hydrocinnamylamine: Similar structure but lacks the hydroxyl group.
These compounds share structural similarities but differ in functional groups, which can significantly impact their chemical behavior and applications.
Propriétés
IUPAC Name |
3-(methylamino)-1-phenylpropan-1-ol |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C10H15NO/c1-11-8-7-10(12)9-5-3-2-4-6-9/h2-6,10-12H,7-8H2,1H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
XXSDCGNHLFVSET-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CNCCC(C1=CC=CC=C1)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C10H15NO |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID40866081 |
Source
|
| Record name | 3-(Methylamino)-1-phenyl-1-propanol | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID40866081 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
165.23 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
42142-52-9 |
Source
|
| Record name | 3-(Methylamino)-1-phenyl-1-propanol | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=42142-52-9 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | 3-Methylamino-1-phenylpropanol | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0042142529 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | 3-(Methylamino)-1-phenyl-1-propanol | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID40866081 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | α-[2-(methylamino)ethyl]benzyl alcohol | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.050.600 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | 3-METHYLAMINO-1-PHENYLPROPANOL | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/I28ND993BO | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
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Retrosynthesis Analysis
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Strategy Settings
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| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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