Buy 1-Chloro-N-methyl-1-phenyl-2-propanamine
Buy 1-Chloro-N-methyl-1-phenyl-2-propanamine
- Structure: This compound is a halogenated derivative of N-methylamphetamine, where a chlorine atom is attached to the beta-position (1-position) of the phenylpropan-2-amine backbone.
- Synonyms: (1S,2S)-1-chloro-N-methyl-1-phenylpropan-2-amine; beta-Chloro-N,alpha-dimethylphenethylamine hydrochloride; CID 12684824. Buy 1-Chloro-N-methyl-1-phenyl-2-propanamine
- Properties: It is often studied as a hydrochloride salt.
- Context: It is closely related to stimulant compounds and phenethylamine derivatives.
- Clobenzorex: A stimulant drug containing a chlorinated phenyl group, N-[(2-chlorophenyl)methyl]-1-phenylpropan-2-amine.
- 1-Phenyl-1-chloro-2-methyl-aminopropane: A similar chloro-substituted stimulant, identified by CID 129668303.
1-Chlor-N-methyl-1-phenyl-2-propanamin Buy 1-Chloro-N-methyl-1-phenyl-2-propanamine
[German]
1-Chloro-N-methyl-1-phenyl-2-propanamine
Benzeneethanamine, β-chloro-N,α-dimethyl-
1-Chloro-N-methyl-1-phenyl-2-propanamine
- 1-Chloro-N-methyl-1-phenyl-2-propanamine
- 1-Phenyl-1-chloro-2-methylamino propane
- PD044907
- NS00017731
- NS00096460
1 Structures
1-Chloro-N-methyl-1-phenylpropan-2-amine hydrochloride (CAS RN: 25394-24-5), also known as chloropseudoephedrine or chloroephedrine, is a chloro-substituted derivative of the phenethylamine class. Structurally, it consists of a phenyl ring attached to a propan-2-amine backbone with a chlorine atom at the 1-position and a methyl group on the nitrogen (). This compound is closely related to ephedrine and pseudoephedrine but distinguished by the presence of a chlorine substituent, which significantly alters its physicochemical and pharmacological properties.
The compound is often identified via attenuated total reflectance Fourier-transform infrared (ATR-FTIR) spectroscopy, with characteristic absorption peaks such as the C-Cl stretch at ~680 cm⁻¹ (). Its hydrochloride salt form enhances stability and solubility, making it relevant in pharmaceutical and forensic contexts, particularly in the analysis of controlled substances ().
Properties
CAS No. |
25394-33-6 |
|---|---|
Molecular Formula |
C10H15Cl2N |
Molecular Weight |
220.14 g/mol |
IUPAC Name |
1-chloro-N-methyl-1-phenylpropan-2-amine;hydrochloride |
InChI |
InChI=1S/C10H14ClN.ClH/c1-8(12-2)10(11)9-6-4-3-5-7-9;/h3-8,10,12H,1-2H3;1H |
InChI Key |
ICZRAESMLGJTOQ-UHFFFAOYSA-N |
Canonical SMILES |
CC(C(C1=CC=CC=C1)Cl)NC.Cl |
Origin of Product |
United States |
Preparation Methods
General Synthetic Approaches
The synthesis of 1-chloro-N-methyl-1-phenylpropan-2-amine hydrochloride typically involves chlorination and amination steps on a phenylpropan derivative. The main routes reported in the literature and patents include:
- Nucleophilic substitution of chlorinated phenylpropane intermediates with methylamine
- Mannich-type reactions involving formaldehyde, methylamine hydrochloride, and phenyl-substituted ketones
- Halogenation of N-methyl-1-phenylpropan-2-amine followed by salt formation with hydrochloric acid
These methods are optimized to maximize yield and purity while minimizing side reactions such as elimination or over-chlorination.
Detailed Synthetic Procedure
A representative synthetic route is as follows:
- Starting Material: 1-phenylpropan-2-one or its derivatives are used as precursors.
- Mannich Reaction: React the ketone with formaldehyde and methylamine hydrochloride under reflux in ethanol or an appropriate solvent to form the N-methylated amine intermediate.
- Chlorination: The intermediate undergoes selective chlorination at the benzylic position using reagents such as thionyl chloride or phosphorus pentachloride under controlled temperature to yield the chloro-substituted amine.
- Salt Formation: The free base is treated with hydrochloric acid to form the hydrochloride salt, which improves stability and crystallinity.
- Purification: The product is purified by recrystallization from ethanol/water mixtures or by chromatographic methods to achieve ≥98% purity.
Industrial Scale Production
Industrial synthesis utilizes continuous flow reactors to enhance reaction control, yield, and scalability. Automated systems allow precise temperature and stoichiometric control, reducing side products such as Hofmann elimination byproducts. Purification often involves silica gel chromatography followed by recrystallization.
Reaction Conditions and Optimization
| Step | Reagents/Conditions | Notes |
|---|---|---|
| Mannich Reaction | Formaldehyde (polymer or paraformaldehyde), methylamine hydrochloride, ethanol, reflux | Methylene-active ketone required; reaction monitored by TLC or NMR |
| Chlorination | Thionyl chloride or PCl5, inert solvent (e.g., dichloromethane), 0–25°C | Controlled to avoid over-chlorination or elimination |
| Salt Formation | HCl gas or aqueous HCl, room temperature | Ensures hydrochloride salt formation for stability |
| Purification | Recrystallization (ethanol/water) or silica gel chromatography | Achieves high purity for analytical use |
Analytical Characterization
- Nuclear Magnetic Resonance (NMR):
- ^1H NMR shows characteristic signals for the N-methyl group (~2.2–2.4 ppm, singlet), aromatic protons (~7.2–7.5 ppm), and methine/methylene protons adjacent to chlorine and amine groups.
- ^13C NMR confirms carbon environments consistent with chlorinated phenylpropylamine structure.
- Mass Spectrometry (MS):
- Molecular ion peak at m/z ~220 consistent with C10H15Cl2N. Chlorine isotopic pattern confirms presence of chlorine atoms.
- High-Performance Liquid Chromatography (HPLC):
- Used for purity assessment, with UV detection at ~255 nm.
- X-ray Crystallography:
- Provides definitive structural confirmation and insight into crystal packing and hydrogen bonding in the hydrochloride salt form.
Summary Table of Preparation Methods
| Method | Starting Materials | Key Reagents/Conditions | Yield (%) | Purification Method | Notes |
|---|---|---|---|---|---|
| Mannich Reaction + Chlorination | 1-phenylpropan-2-one, methylamine hydrochloride, formaldehyde | Reflux in ethanol, thionyl chloride chlorination | 70–85% | Recrystallization, chromatography | Common lab-scale method |
| Direct Amination of Chloropropane | 3-chloro-1-phenylpropan-2-one, methylamine | Solvent reflux (ethanol, chloroform) | 65–80% | Chromatography, recrystallization | Industrially scalable |
| Halogenation of N-methyl-1-phenylpropan-2-amine | N-methyl-1-phenylpropan-2-amine, PCl5 | Low temperature chlorination | 60–75% | Recrystallization | Requires strict temperature control |
Chemical Reactions Analysis
1-chloro-N-methyl-1-phenylpropan-2-amine hydrochloride undergoes various chemical reactions, including:
Oxidation: This compound can be oxidized to form corresponding ketones or carboxylic acids, depending on the oxidizing agent and reaction conditions.
Reduction: Reduction reactions can convert the compound into its corresponding amine or alcohol derivatives.
Common reagents used in these reactions include oxidizing agents like potassium permanganate, reducing agents like lithium aluminum hydride, and nucleophiles like sodium hydroxide. The major products formed from these reactions depend on the specific reagents and conditions used .
Scientific Research Applications
1-chloro-N-methyl-1-phenylpropan-2-amine hydrochloride has several scientific research applications:
Chemistry: It is used as a precursor in the synthesis of various organic compounds and as a reagent in chemical reactions.
Biology: The compound is studied for its potential effects on biological systems, including its interactions with enzymes and receptors.
Mechanism of Action
The mechanism of action of 1-chloro-N-methyl-1-phenylpropan-2-amine hydrochloride involves its interaction with molecular targets, such as enzymes and receptors. The compound can act as an inhibitor or activator of specific enzymes, leading to changes in biochemical pathways. Its effects on receptors can modulate cellular signaling and physiological responses .
Comparison with Similar Compounds
Key Observations :
- The position of chlorine (e.g., on the propane chain vs. aromatic ring) influences electronic properties and bioactivity.
Spectroscopic Differentiation
Infrared spectroscopy effectively distinguishes this compound from analogues:
| Compound | C-Cl Stretch (cm⁻¹) | N-H Stretch (cm⁻¹) | Aromatic C-H Bending (cm⁻¹) | |
|---|---|---|---|---|
| This compound | 680 | 2550–2650 | 700–750 | |
| Ephedrine HCl | Absent | 2500–2600 | 700–750 | |
| Pseudoephedrine HCl | Absent | 2500–2600 | 700–750 | |
| N-(4-Chlorobenzyl)-1-phenyl-2-propanamine HCl | 740 (C-Cl on benzyl) | 2550–2650 | 700–750 |
The C-Cl stretch at ~680 cm⁻¹ is a unique identifier for this compound, absent in non-chlorinated analogues like ephedrine ().
Pharmacological and Regulatory Considerations
- 2-Phenyl-1-propanamine HCl : Lacks chlorine, reducing halogen-mediated interactions; historically used in decongestants but less potent than ephedrine ().
- N-(4-Chlorobenzyl)-1-phenyl-2-propanamine HCl : The chlorobenzyl group may confer distinct receptor affinity, though toxicity profiles remain unstudied ().
Regulatory Status : Chloroephedrine is monitored under controlled substance regulations due to its structural resemblance to ephedrine, a precursor in illicit drug synthesis ().
Biological Activity
1-Chloro-N-methyl-1-phenylpropan-2-amine hydrochloride, commonly referred to as 1-chloro-N-methyl-1-phenylpropan-2-amine HCl, is a compound of significant interest in both medicinal chemistry and forensic science. This article explores its biological activity, including pharmacological effects, toxicity, and relevant case studies.
The molecular formula of this compound is C10H14ClN, with a molecular weight of approximately 183.68 g/mol. The compound features a chloro substituent on a secondary amine, contributing to its unique biological properties.
| Property | Value |
|---|---|
| Molecular Formula | C10H14ClN |
| Molecular Weight | 183.68 g/mol |
| Density | 1.0 ± 0.1 g/cm³ |
| Boiling Point | 251.9 ± 28.0 °C |
| Flash Point | 106.1 ± 24.0 °C |
| LogP | 1.95 |
Pharmacological Effects
Research indicates that compounds similar to this compound exhibit stimulant properties akin to amphetamines. These effects include increased alertness, energy, and potential euphoria, which are primarily mediated through the release of neurotransmitters such as dopamine and norepinephrine.
Mechanism of Action:
The compound acts as a monoamine releasing agent, particularly affecting the dopaminergic system. This mechanism is similar to that of methamphetamine but with variations due to the presence of the chlorine atom.
Toxicity and Safety
Toxicological studies have shown that compounds in this class can lead to adverse effects such as cardiovascular issues, neurotoxicity, and dependency. The hydrochloride salt form is often evaluated for its stability and solubility, which are critical for assessing its safety profile.
Case Studies:
- Forensic Analysis : A study highlighted the importance of identifying intermediates like this compound in illicit drug synthesis. Analytical techniques such as GC/MS and NMR were utilized to determine the stereochemical properties of synthesized methamphetamine derivatives, providing insights into their potential impacts on human health .
- Clinical Observations : Reports from clinical settings have documented cases where patients presented with symptoms consistent with stimulant overdose after exposure to substances containing this compound or its analogs.
Research Findings
Recent research has focused on the synthesis pathways and impurity profiles associated with the production of this compound. Notably, studies have employed chiral analysis techniques to differentiate between various stereoisomers produced during synthesis .
Table: Summary of Research Findings
1-Chloro-N-methyl-1-phenyl-2-propanamine – PubChem
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