1. Product Overview
(S)-2-(Adamantan-1-yl)-2-aminoacetic Acid Hydrochloride (CAS 102502-64-7), also known as (S)-Adamantylglycine Hydrochloride, is the hydrochloride salt of (S)-2-(1-adamantyl)glycine. This chiral amino acid derivative features a bulky, lipophilic adamantane cage attached to the α-carbon, conferring unique steric and electronic properties. It is primarily used as a reference standard/impurity for Saxagliptin (a DPP-4 inhibitor for type 2 diabetes) and as a key chiral building block in pharmaceutical synthesis. The adamantane scaffold is well-known for enhancing metabolic stability, membrane permeability, and bioavailability in drug candidates.
2. Key Features and Benefits
• Chiral Purity: Supplied as the single (S)-enantiomer with ≥95% or ≥98% enantiomeric purity, ensuring reliable results in asymmetric synthesis and analytical method development.
• Adamantane Advantage: The tricyclic [3.3.1.1³,⁷]decane cage provides exceptional lipophilicity (LogP ~3.1), rigid three-dimensional structure, and resistance to metabolic degradation—highly desirable in drug design.
• Water-Soluble Salt Form: The hydrochloride salt significantly improves aqueous solubility compared to the free base, facilitating easy handling in both organic synthesis and bioassays.
• Dual Functional Groups: The free amino group (as NH₃⁺Cl⁻) and carboxylic acid enable standard peptide coupling (amide bond formation) and further N-alkylation/a-acylation for SAR studies.
• Well-Characterized: Full spectral data (¹H/¹³C NMR, MS, HPLC) available from multiple suppliers; suitable for use as an analytical reference standard (CNAS/ISO 17034 certified options available).
3. Major Applications
• Saxagliptin Impurity Reference Standard: Officially listed as Saxagliptin Impurity 36/56; used for analytical method development, QC testing, and regulatory filing (ANDA) support in Saxagliptin API manufacturing.
• Peptide & Peptidomimetic Synthesis: Employed as a chiral, lipophilic amino acid building block in solid-phase peptide synthesis (SPPS) to introduce the adamantylglycine residue into bioactive peptides.
• Drug Discovery Building Block: The adamantane moiety is a privileged structure in antiviral (Amantadine, Rimantadine), anti-Parkinson's, and DPP-4 inhibitor drug classes; this compound enables rapid SAR exploration.
• Chiral Ligand Development: The rigid, enantiomerically pure scaffold can be incorporated into ligands for asymmetric catalysis (e.g., organocatalysis, metal-complex catalysts).
• Academic Research: Studied in glycine receptor agonist/antagonist design and central nervous system (CNS) active compound development.
4. Technical Specifications
Item Description
Product Name (S)-2-(Adamantan-1-yl)-2-aminoacetic Acid Hydrochloride
Synonyms (S)-Adamantylglycine Hydrochloride; (S)-(+)-(Adamant-1-yl)aminoacetic acid hydrochloride; Saxagliptin Impurity 36; Saxagliptin Impurity 56; (S)-2-(1-Adamantyl)glycine HCl
CAS Number 102502-64-7
Molecular Formula C₁₂H₁₉NO₂ · HCl (C₁₂H₂₀ClNO₂)
Molecular Weight 245.75 g/mol
MDL Number MFCD16657120
Assay (Purity) ≥95% / ≥98% (HPLC)
Enantiomeric Purity ≥98% ee (S)
Appearance White to off-white crystalline solid or powder
Melting Point Not reported (typical for amino acid HCl salts: 200–260 °C, often decomposes)
Boiling Point Not determined (decomposes)
Density ~1.25 g/cm³ (Predicted)
pKa (Predicted) ~2.1 (COOH); ~9.8 (NH₃⁺)
Calculated LogP ~3.12
Polar Surface Area (PSA) 63.32 Ų
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
Rotatable Bonds 2
Solubility Soluble: Water (as HCl salt), Methanol, Ethanol, DMSO, DMF, Acetic acid.
Slightly Soluble:DCM, THF, Acetone.
Insoluble:Hexane, Ether.
Spectral Data ¹H NMR (DMSO‑d₆, 400 MHz): δ 1.25–2.05 (m, 15H, adamantane CH/CH₂), 3.15 (br s, 3H, NH₃⁺), 4.10 (s, 1H, CHCOOH), 12.5 (br s, 1H, COOH).
¹³C NMR (DMSO‑d₆):δ 28.0, 32.5, 36.5, 39.0 (adamantane Cs), 55.5 (CHCOOH), 170.0 (COOH).
SMILES OC(=O)[C@](C12CC3CC(CC(C3)C1)C2)([NH3+])[Cl-]
InChI Key HEUUMSMIQNBXML-FQPTWHMNSA-N
Storage (Powder) Room Temperature or 2–8 °C, sealed, protected from light & moisture; stable ≥18–24 months
HS Code 2922.49.90 / 3822.90.00 (Reference Standard)
5. Storage and Handling
• Storage: Store in a tightly sealed container at room temperature or 2–8 °C, protected from light and moisture. The hydrochloride salt is hygroscopic to a moderate degree; a desiccator is recommended for long-term storage (>12 months). Stable for at least 18–24 months from date of manufacture.
• Handling: Allow vial to reach room temperature before opening to prevent moisture condensation. Dissolve in water, MeOH, EtOH, DMSO, or DMF as required. The HCl salt form ensures good aqueous solubility—filter if any undissolved particulate remains.
• Solution Stability: Aqueous or methanolic solutions are stable for several days at RT; for long-term storage, aliquot and freeze at -20 °C. Avoid repeated freeze-thaw cycles.
• Deprotection/Modification: The amino group can be liberated from the HCl salt by treatment with 1 eq. of base (NaOH, K₂CO₃) in aqueous/organic solvent, then extracted as the free base if needed for coupling reactions.
6. Safety Summary (Full SDS Highlights)
• GHS Classification: GHS07 – Warning
• Signal Word: Warning
• Hazard Statements:
• H303: May be harmful if swallowed.
• H313: May be harmful in contact with skin.
• H333: May be harmful if inhaled.
• H315: Causes skin irritation.
• H319: Causes serious eye irritation.
• Precautionary Statements:
• P261: Avoid breathing dust/mist/vapors. Use only in a well-ventilated area or fume hood.
• P264: Wash hands, forearms, and face thoroughly after handling.
• P270: Do not eat, drink, or smoke in areas where this material is used.
• P271: Use only outdoors or in a well-ventilated area.
• P280: Wear protective gloves (nitrile), safety glasses with side shields, and lab coat.
• P301+P312: IF SWALLOWED: Call a POISON CENTER or physician if you feel unwell.
• P302+P352: IF ON SKIN: Wash with plenty of soap and water.
• P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
• P330: Rinse mouth if swallowed.
• P337+P313: If eye irritation persists: Get medical advice/attention.
• P403+P233: Store in a well-ventilated place. Keep container tightly closed.
• P501: Dispose of contents/container in accordance with local, regional, and national regulations.
• First Aid Measures:
• Inhalation: Remove to fresh air. If breathing difficult, administer oxygen and seek medical attention.
• Skin Contact: Immediately wash with plenty of soap and water. Remove contaminated clothing. Seek medical advice if irritation or rash develops.
• Eye Contact: Flush immediately with copious lukewarm water for at least 15 minutes. Remove contact lenses if possible. Seek medical attention.
• Ingestion: Rinse mouth. Do NOT induce vomiting. Give water to drink if conscious. Seek medical advice.
• Fire-Fighting Measures:
• Suitable Extinguishing Media: Water spray, alcohol-resistant foam, dry chemical, or CO₂.
• Special Hazards: Combustion may produce irritating/acrid smoke (HCl, CO, NOₓ).
• Protective Equipment: Wear self-contained breathing apparatus (SCBA) and full protective clothing.
• Spill Response:
• Avoid dust generation. Sweep up and place in a suitable closed container for disposal. Do not allow entry to drains or waterways. Ventilate area after cleanup.
• Handling & Storage:
• Handle in fume hood. Keep container closed when not in use. Store at room temperature or 2–8 °C, protected from light and moisture. Keep away from strong oxidizers and strong bases.
• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use. Handle as a potentially bioactive compound.
