1 Aminoadamantane-2,2,2′,2′,2”,2”-d6 | CAS 1219805-53-4

OVERVIEW
1-Aminoadamantane-2,2,2′,2′,2″,2″-d₆ is a deuterium-labelled analogue of 1-aminoadamantane, more commonly known as amantadine. This compound features six deuterium atoms replacing six hydrogen atoms within the adamantane cage structure. The result is a stable isotopic variant that maintains the same physicochemical and pharmacological properties as the non-deuterated parent molecule while providing distinct advantages for analytical, pharmacokinetic, and tracer studies.

Deuterated amantadine analogues such as 1-Aminoadamantane-2,2,2′,2′,2″,2″-d₆ are of significant importance in modern research. Their structural similarity and isotopic enrichment allow for accurate tracking in biological systems, mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy. The compound’s robust molecular framework and high chemical stability make it particularly well-suited for use as an internal standard in pharmaceutical analysis and metabolism studies.

CHEMICAL INFORMATION

•  Name: 1-Aminoadamantane-2,2,2′,2′,2″,2″-d₆

• Molecular Formula: C₁₀H₁₁D₆N

• Molecular Weight: 161.32 g/mol

• CAS Number: 1219805-53-4

• Isotopic Enrichment: ≥ 98 atom % D

• Chemical Class: Deuterated aliphatic amine; adamantane derivative

• Stability: Excellent thermal and chemical stability; resistant to oxidation and hydrolysis under normal laboratory conditions

APPLICATIONS

• Pharmaceutical Research and Drug Metabolism:
  1-Aminoadamantane-2,2,2′,2′,2″,2″-d₆ serves as a valuable internal standard in pharmacokinetic studies involving amantadine, a well-known antiviral and antiparkinsonian agent. The deuterium label allows differentiation of the tracer molecule from its non-deuterated counterpart in biological matrices using mass spectrometric techniques.

• Mass Spectrometry (MS):
  The +6 Da mass shift due to deuterium incorporation makes this compound an ideal isotope-labelled standard for LC-MS and GC-MS quantification of amantadine in plasma, urine, or tissue samples. It ensures precise quantification by correcting for matrix effects and instrumental variations.

• NMR Spectroscopy:
  In NMR experiments, the presence of deuterium significantly reduces proton signal overlap, improving resolution and aiding in structural elucidation of adamantane-based compounds.

• Mechanistic and Kinetic Studies:
  The kinetic isotope effect (KIE) associated with deuterium substitution can be utilized to study the mechanistic details of enzymatic reactions, hydrogen transfer processes, or metabolic degradation involving adamantane derivatives.

• Reference Standard for Quality Control:
  Widely used as a stable isotopic reference in analytical laboratories to validate and calibrate analytical methods for drugs containing the adamantane framework.

• Tracer in Biological Systems:
  Employed as a metabolic tracer to investigate absorption, distribution, metabolism, and excretion (ADME) pathways of adamantane-based compounds in preclinical and clinical studies.

ADVANTAGES

• High isotopic purity ensures accurate mass spectral distinction.

• Chemically identical to the native amantadine, allowing direct comparative analysis.

• Enhanced analytical reliability in quantitative bioanalysis.

• Low volatility and high stability suitable for long-term storage and repeated use.

• Useful for tracing metabolic transformations without altering biological activity.

• Suitable for a wide range of analytical methods including HPLC-MS/MS, GC-MS, and NMR spectroscopy.

HANDLING
1-Aminoadamantane-2,2,2′,2′,2″,2″-d₆ should be handled following standard laboratory safety guidelines.

• Avoid inhalation of dust and contact with skin or eyes.

• Use protective gloves, goggles, and appropriate laboratory attire.

• Handle in a well-ventilated workspace.

• Store in airtight containers under ambient or slightly cool conditions, away from moisture and strong oxidisers.

• Stable under normal conditions; decomposition may occur upon exposure to high heat or open flame.

QUALITY & SPECIFICATION
Each batch of 1-Aminoadamantane-2,2,2′,2′,2″,2″-d₆ is tested to confirm identity, purity, and isotopic enrichment using advanced analytical techniques such as NMR spectroscopy, high-resolution mass spectrometry (HRMS), and infrared spectroscopy.

• Chemical Purity: ≥ 98 %

• Isotopic Enrichment: ≥ 98 atom % D

• Residual Solvents: Within ICH limits

• Analytical Verification: Each lot is accompanied by a Certificate of Analysis (COA) to ensure traceability and quality assurance.

SUMMARY
1-Aminoadamantane-2,2,2′,2′,2″,2″-d₆ (CAS 1219805-53-4) is a deuterium-labelled analogue of amantadine designed for precision analytical and pharmacological applications. Its stable isotopic composition, identical structural integrity, and excellent physical properties make it ideal for use as an internal standard, tracer, and research reagent in mass spectrometry, NMR spectroscopy, and metabolic studies. This compound plays a vital role in modern analytical chemistry and biomedical research, facilitating accurate quantitation, mechanistic exploration, and isotopic labelling studies in a wide range of scientific disciplines.