N,N-Dimethylglycine
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Product Description
N,N-Dimethylglycine is a water-soluble, naturally occurring derivative of glycine—essentially the amino acid “upgraded” with two extra methyl groups—that shuttles between plant, animal and human metabolism as a non-essential intermediary. Sold as a white crystalline “vitamin-like” supplement (formerly B16), it is promoted to enhance human stamina, immunity, cardiovascular and neurological health by feeding the universal methyl cycle, buffering oxidative stress and supporting mitochondrial oxygen use, though large-scale clinical proof remains sparse and FDA has approved no therapeutic claims. The same low-toxicity (50–200 mg/day) molecule is routinely added to pet and livestock diets to improve growth, liver function and stress resistance, while industry exploits its amphoteric structure as a surfactant precursor and versatile chemical intermediate.
Other Information
Research Highlights
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NMDA Receptor Modulation: Acts as a partial agonist; potential therapeutic interest in schizophrenia, depression, and autism.
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Antioxidant in Embryo Development: Enhances bovine blastocyst formation under oxidative stress in vitro.
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Environmental Benefit: Reduces nitrogen excretion in poultry manure when used as feed additive.
Regulatory & Commercial Notes
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Formerly called “Vitamin B16” or pangamic acid, but not a true vitamin.
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Marketed mainly as a dietary supplement and animal feed additive.
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Production methods evolving toward greener processes (e.g., BMED).
Synthesis and Production
Chemical Synthesis Methods
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Primary Route: Reaction of chloroacetic acid with dimethylamine yields dimethylglycine hydrochloride, which is further processed to obtain DMG.
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Other Methods:
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Ion exchange resin method (generates saline wastewater).
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Extraction crystallization using organic solvents (e.g., ethanol), which is costly and generates waste.
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Advanced Recovery Method
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Bipolar Membrane Electrodialysis (BMED):
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Used to recover DMG from dimethylglycine hydrochloride.
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Configuration: Two-compartment cell (BP-A) to prevent macromolecular migration and membrane fouling.
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Optimal conditions: Current density 50 A/m², feed concentration 0.3 M, flow rate 15 L/h.
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Results: 98% recovery, energy consumption 0.45 kWh/kg, current efficiency 65%, minimal membrane fouling.
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Advantages: High purity, no by-products, environmentally friendly, suitable for industrial scale-up.
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Uses and Applications
Human Health & Dietary Supplements
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Reported Benefits (note: many lack robust clinical validation):
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Energy and endurance enhancement (oxygen utilization).
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Immune system modulation.
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Cardiovascular support (homocysteine reduction, antioxidant).
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Neurological and cognitive support (involvement in choline/neurotransmitter metabolism).
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Autism spectrum support (anecdotal improvements in behavior/language).
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Regulatory Status: Not approved by FDA for disease treatment; considered a dietary supplement.
Animal Nutrition & Health
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Pet Supplements: Used for immune function, liver health, and anti-aging in dogs.
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Livestock Feed Additive: Improves growth performance, stress resistance, and digestibility.
Industrial & Research Applications
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Chemical Intermediate: Synthesis of more complex compounds.
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Surfactant Raw Material: Used in personal care products due to its amphoteric structure.
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Research Tool: Model compound in studies of amino acid metabolism, enzyme mechanisms, and oxidative stress.
Chemical and Physical Properties
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Molecular Formula: C₄H₉NO₂
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Molecular Weight: 103.12 g/mol
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Appearance: White crystalline powder.
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Melting Point: 185.5 °C
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Boiling Point: 63.9 °C
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Solubility: Highly soluble in water.
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LogP: -2.91 (hydrophilic)
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pKa: ~2.04 (acidic)
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Hydrogen Bond Donors/Acceptors: 1 donor, 3 acceptors.
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Polar Surface Area: 40.5 Ų
Structural & Crystallographic Features
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Crystal Structures:
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Anhydrous DMG: Forms R₄⁴(20) ring motifs; no “head-to-tail” hydrogen-bonded chains.
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Hemihydrate (DMG·0.5H₂O): Infinite C₂²(10) head-to-tail chains linked via N–H···O bonds; water molecules bridge carboxylate groups.
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Reactivity: Undergoes oxidative stress with H₂O₂, forming perhydrate crystals and hydroxylamine derivatives.
Biological & Metabolic Properties
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Metabolic Role: Intermediate in choline → betaine → DMG → sarcosine → glycine pathway.
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Natural Occurrence: Found in beans, grains, animal liver, and human metabolism.
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Mechanisms of Action:
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Methyl group donor (precursor to betaine).
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Antioxidant (protects against oxidative stress, supports glutathione synthesis).
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Enhances nutrient digestibility (emulsifying action).
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NMDA receptor modulation (partial agonist at glycine binding site).
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Safety and Handling
Toxicological Profile
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General Safety: Low toxicity; well-tolerated in humans at typical doses (50–200 mg/day).
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Animal Studies (broilers):
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No adverse effects at 1 g/kg feed.
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No bioaccumulation in meat/liver at 1 g/kg; mild accumulation at 10 g/kg (still within safe limits comparable to common foods).
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No pathological changes in hematology, biochemistry, or histopathology.
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Human Studies: No toxicity reported at 300–600 mg/day for 28 days.
Potential Side Effects
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Minor gastrointestinal discomfort, headache, or insomnia (especially if taken at night).
Precautions & Interactions
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Drug Interactions: Possible interactions with anticoagulants, antihypertensives, and immunosuppressants.
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Special Populations: Insufficient safety data for pregnant or breastfeeding women; use not recommended.
Handling & Storage
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Stable solid under normal conditions.
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No specific hazardous handling requirements noted (irritant symbol may apply per GHS).