N,N-Dimethylglycine hydrochloride
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Product Description
N,N-dimethylglycine hydrochloride (DMG·HCl) is a white crystalline powder obtained by dimethylating glycine and then forming a salt with hydrochloric acid. It has good water solubility and high stability. Industrially, it is mainly produced via the "dimethylamine + chloroacetic acid" route (yield >90%, purity ≥99%). After entering the body, it rapidly releases DMG, which acts as a methyl donor in one-carbon metabolism. This can enhance mitochondrial ATP synthesis, provide anti-inflammatory and antioxidant effects, and support the methylation cycle. Therefore, it is used in sports nutrition, immune regulation, auxiliary research for depression/autism, and supportive cancer treatment. Due to its hygroscopic and osmotic properties, it is also used as an ingredient in moisturizing and anti-aging cosmetics. Furthermore, it promotes growth and reduces stress in animal feed and serves as a plating brightener and an intermediate in organic synthesis.
Other Information
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Related Compounds:
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Parent Compound: CID 673 (N,N-Dimethylglycine), which is the active moiety.
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Component Compounds: CID 673 and CID 313 (Hydrochloric Acid).
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Biologic Depiction: In the context of glycobiology, it has IUPAC condensed notations like "Me-Sar-OH.HCl".
Synthesis and Production
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Primary Synthetic Route (Industrial): The predominant industrial method involves the reaction of dimethylamine with chloroacetic acid, followed by acidification and crystallization to form the hydrochloride salt. This process is noted for mild reaction conditions and high yields (exceeding 90%).
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Alternative Route: Can also be synthesized via the methylation of glycine using formaldehyde and formic acid (Eschweiler-Clarke reaction), followed by salt formation.
Uses and Applications
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Nutritional Supplements & Health Products: Marketed for human consumption with claims related to enhancing energy metabolism, improving athletic performance and endurance, supporting immune function, and acting as an antioxidant and methyl donor. Its use in conditions like depression, epilepsy, and autism is noted as an area of research.
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Animal Nutrition: Widely used as a feed additive in livestock and aquaculture to improve growth performance, feed conversion efficiency, anti-stress capability, and overall metabolism.
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Cosmetics & Personal Care: Utilized in skincare formulations (e.g., moisturizers, anti-aging products) for its humectant properties and potential to promote skin penetration and support barrier repair.
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Pharmaceutical Intermediates: Serves as a building block or active moiety for synthesizing other compounds like betaine and surfactants.
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Industrial & Research Applications: Used as an additive in electroplating to improve coating quality and as a biochemical reagent or buffer component in scientific research.
Chemical and Physical Properties
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Physical Form: White to off-white crystalline powder.
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Molecular Formula: C₄H₉NO₂·HCl or C₄H₁₀ClNO₂
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Molecular Weight: 139.58 g/mol (PubChem).
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Solubility: Freely soluble in water.
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Chemical Identifiers:
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CAS Registry Number: 2491-06-7
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InChIKey: FKASAVXZZLJTNX-UHFFFAOYSA-N
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SMILES: CN(C)CC(=O)O.Cl
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UNII: YXK75EAE92
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Computed Properties (PubChem):
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Hydrogen Bond Donor Count: 2
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Hydrogen Bond Acceptor Count: 3
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Topological Polar Surface Area: 40.5 Ų
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Heavy Atom Count: 8
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Spectral Data: Experimental ¹H NMR, ¹³C NMR, IR (FTIR, ATR-IR), and Raman spectra are available in PubChem from sources like SpectraBase (Wiley).
Safety and Handling
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GHS Classification (ECHA): Based on notified classifications, it may carry the following hazard statements (with varying certainty among reports):
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H315: Causes skin irritation (54.5% of reports).
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H319: Causes serious eye irritation (54.5% of reports).
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H335: May cause respiratory irritation (54.5% of reports).
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Signal Word: Warning
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Pictogram: GHS07 (Exclamation mark)
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Precautionary Measures: Recommended precautions include using gloves, eye protection, and ensuring adequate ventilation to avoid dust inhalation. Relevant precautionary statement codes are listed (e.g., P261, P280, P305+P351+P338).
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Toxicity: Considered low in toxicity. An acute effects data link is provided from the ChemIDplus/RTECS database.
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Regulatory Status:
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EU REACH: Registered, with status reported as "Cease Manufacture" (as of 2017 update).
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U.S. TSCA: Listed as "INACTIVE".
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Australia (AICIS) and New Zealand (EPA): Listed in national inventories, with NZ noting it may be used as a component under a group standard.
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FDA: Has a Unique Ingredient Identifier (UNII) and appears in drug labeling information in DailyMed.
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