Para-fluoro methylaminorex
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Product Description
Para-fluoro methylaminorex (4′-fluoro-4-methylaminorex, also known as 4F-MAR or 4'-F-MAR) is a synthetic stimulant belonging to the aminorex family of compounds, which are oxazoline-based stimulants. The structure features an oxazoline ring fused with a substituted phenyl group, including a para-fluoro substitution on the phenyl ring and secondary amine functionality. This compound is structurally related to methylaminorex and other aminorex analogues, with the fluorine atom at the para position typically increasing lipophilicity and potentially altering binding affinity at monoamine transporters. As a designer stimulant, it is not approved for medical use and is illegal in many jurisdictions due to its controlled substance analog status. It poses significant health risks, including cardiovascular stress, potential neurotoxicity, and high addiction potential, making it a dangerous research chemical.
Identification Methods
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Gas Chromatography-Mass Spectrometry (GC-MS)
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Ultra-Performance Liquid Chromatography-Tandem Quadrupole Time-of-Flight Mass Spectrometry (UPLC-QTOF-MS)
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Nuclear Magnetic Resonance (NMR)
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Fourier Transform Infrared Spectroscopy (FTIR)
Synthesis Methods
Known Synthesis Routes:
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General Method: Analogous to 4-methylaminorex, using fluorinated phenyl precursors.
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Convert para-fluoroacetophenone to an oxime or similar intermediate (via hydroxylamine).
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Perform reductive amination with methylamine to attach the amino group.
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Cyclize with a cyanate source (e.g., potassium cyanate) to form the aminorex ring, yielding predominantly trans-4′F-4-MAR.
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Notes:
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The necessary fluorophenyl precursor is often a controlled substance in many countries.
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Synthesis is discussed in clandestine literature, but no controlled synthesis protocols are provided here.
Pharmacology and Effects:
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Mechanism of Action: Acts as a stimulant, similar to other aminorex derivatives. Likely functions as a monoamine releasing agent, affecting neurotransmitters like norepinephrine and dopamine.
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Expected Effects: Euphoria, alertness, energy, and sympathomimetic effects. May cause increased heart rate, blood pressure, and body temperature. Potential for anxiety or agitation at higher doses.
Applications:
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Forensic and Research Use: Used as a reference standard in toxicology and forensic chemistry.
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Recreational Use: Detected as a novel psychoactive substance (NPS) in recreational contexts.
Molecular Formula: C₁₀H₁₁FN₂O
Molar Mass: 194.209 g/mol
IUPAC Name: 4-methyl-5-(4-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine
CAS Number: 1364933-64-1
Synonyms: 4F-MAR, 4-FPO, 4′-fluoro-4-methylaminorex, p-F-4-MAR, 4′-fluoro-4-MAR, 4′-fluoro-4-MAX
Chemical Properties:
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Boiling Point: Approximately 293.6°C
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Density: Approximately 1.32 g/cm³
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Solubility: Good solubility (up to 30 mg/ml in solvents such as DMF, DMSO, and ethanol)
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Physical Form: Crystalline solid
Structural Description:
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Core Structure: Benzene ring with a fluorine atom at the para position (4-fluorophenyl) and an oxazoline ring (1,3-oxazol-2-amine).
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Key Substituents:
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Amino group (-NH₂) attached to the oxazoline ring.
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Methyl group (-CH₃) attached to the oxazoline ring.
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Phenyl ring with a fluorine atom at the para position (4-fluorophenyl).
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Toxicity and Health Effects
Toxicity Profile:
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Cardiovascular Risks: High risk of cardiotoxicity, including tachycardia, arrhythmia, hypertension, and potential for pulmonary hypertension with chronic use.
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Acute Overdose: Can cause life-threatening effects such as extreme agitation, convulsions, hyperthermia, rhabdomyolysis, kidney failure, and disseminated intravascular coagulation.
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Serotonergic Risks: Potential for serotonin syndrome if serotonergic activity is present.
Health Warnings:
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No experimental toxicology data specific to 4′F-4-MAR are available, but related compounds have a notorious safety profile.
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Considered a high-risk stimulant with significant unknown toxicity.
Legal Status
Regulation:
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Italy: Specifically scheduled in 2020.
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European Union: Monitored as a new psychoactive substance (NPS); not uniformly scheduled but potentially controlled under generic NPS rules.
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United Kingdom: Likely illegal under the Psychoactive Substances Act 2016 or analog laws.
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United States: Not explicitly scheduled but treated as an analog of Schedule I 4-MAR under the Federal Analogue Act.
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Canada: Likely controlled as an analog (4-MAR is Schedule III).
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Australia: Considered illegal (akin to other aminorex analogs, which are Schedule 9).
Forensic and Toxicological Reports
Detection:
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Slovenia (2018): Detected in a test-purchase powder containing 4′F-4-MAR.
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United Kingdom (2020): Identified in a powder sample from prison mail.