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Theanine, L-Theanine, N-Ethyl-L-glutamine, 3081-61-6

Theanine, L-Theanine, N-Ethyl-L-glutamine, 3081-61-6

L-THEANINE

1. PRODUCT IDENTIFICATION AND CHEMICAL IDENTITY

Parameter Information
Product Name L-Theanine
Chemical Name L-Glutamic acid γ-ethylamide, L-γ-Glutamylethylamide
CAS Number 3081-61-6
Molecular Formula C₇H₁₄N₂O₃
Molecular Weight 174.20 g/mol
Chemical Class Amino acid / Glutamine analog
Appearance White to off-white crystalline powder
Odor Slight characteristic odor
Physical State (20°C) Solid (crystalline powder)

2. CHEMICAL STRUCTURE

2.1. Molecular Structure

L-Theanine is a unique amino acid found almost exclusively in tea plants (Camellia sinensis). It is an analog of glutamine and glutamic acid, with an ethylamide group replacing the amine group. The molecule consists of a glutamic acid backbone with an ethylamine side chain, forming a γ-glutamyl linkage.

Structural Formula:

        COOH
         |
    H₂N — C — H
         |
        CH₂
         |
        CH₂
         |
         C = O
         |
        NH
         |
        CH₂
         |
        CH₃

Molecular Structure Properties:

Property Description
Functional Groups Carboxyl group (-COOH), amino group (-NH₂), amide group (-CONH-)
Chirality L-isomer (naturally occurring)
Amino Acid Type Non-proteinogenic amino acid
Glutamate Analog Structural analog of L-glutamic acid

2.2. Physicochemical Properties

Property Description
pKa (COOH) ~2.1
pKa (NH₂) ~9.2
Isoelectric Point (pI) ~5.6
Optical Rotation [α]D20 = -8.0° to -10.0°
Molecular Weight 174.20 g/mol
Chemical Formula C₇H₁₄N₂O₃

3. PHYSICAL AND CHEMICAL PROPERTIES

Property Value / Description
Appearance White to off-white crystalline powder
Odor Slight characteristic odor
Molecular Formula C₇H₁₄N₂O₃
Molecular Weight 174.20 g/mol
Purity ≥ 98.0% (typical)
Melting Point 195 – 205 °C
Density ~1.2 g/cm³
Solubility (Water, 25°C) ~13 g/L (freely soluble)
Solubility (Ethanol) Slightly soluble
Solubility (Chloroform) Insoluble
Solubility (Ether) Insoluble
pH (1% aqueous solution) 5.0 – 6.0
Hygroscopicity Moderate (low hygroscopicity)
Optical Rotation [α]D20 = -8.0° to -10.0°
Heavy Metals (as Pb) ≤ 10 ppm
Loss on Drying ≤ 1.0%
Residue on Ignition ≤ 0.1%
Chloride (Cl⁻) ≤ 0.1%
Sulfate (SO₄²⁻) ≤ 0.1%
Arsenic (As) ≤ 3 ppm
Lead (Pb) ≤ 2 ppm
Mercury (Hg) ≤ 1 ppm

4. STABILITY AND REACTIVITY

Parameter Information
Chemical Stability Stable under normal conditions; sensitive to light and moisture
Conditions to Avoid Light, high temperature, moisture, strong acids, strong bases
Incompatible Materials Strong oxidizing agents, strong acids, strong bases
Hazardous Decomposition Products Carbon monoxide, carbon dioxide, nitrogen oxides
Hazardous Polymerization Will not occur
Light Sensitivity Moderate; protect from direct sunlight
Moisture Sensitivity Moderate; caking may occur in high humidity
Thermal Stability Decomposes above 205°C

5. BIOLOGICAL AND FUNCTIONAL PROPERTIES

5.1. Mechanism of Action

L-Theanine exerts its effects through multiple mechanisms. It crosses the blood-brain barrier via the large neutral amino acid transporter (LAT1) and influences various neurotransmitter systems in the brain.

Primary Mechanisms:

Mechanism Description
Glutamate Antagonism Competes with glutamate for binding sites at glutamate receptors
GABA Enhancement Increases GABA levels through glutamate conversion
α2δ-1 Subunit Binding Binds to voltage-gated calcium channels (α2δ-1 subunit)
NMDA Receptor Modulation Allosteric modulation of NMDA receptors
BDNF Increase Increases brain-derived neurotrophic factor (BDNF)

5.2. Biological Activities

Activity Description
Relaxation (Alpha Waves) Increases alpha brain wave activity; promotes relaxation without drowsiness
Focus and Cognition Enhances attention, focus, and cognitive performance
Stress Reduction Reduces subjective stress and anxiety; decreases cortisol levels
Sleep Quality Improves sleep quality and duration (synergistic with GABA)
Neuroprotection Protects against glutamate excitotoxicity and oxidative stress
Blood Pressure Regulation Modest reduction in blood pressure
Immune Function Supports immune function
Anti-inflammatory Reduces inflammatory markers
Caffeine Synergy Works synergistically with caffeine: improves focus while reducing jitteriness

5.3. Caffeine Synergy

Effect Caffeine Caffeine + L-Theanine
Alertness High High
Jitteriness High Reduced
Focus Moderate Enhanced
Heart Rate Increased Moderated
Alpha Waves Decreased Increased
Calmness Decreased Enhanced
Crash Effect Common Reduced

Optimal Ratio: 2:1 L-Theanine : Caffeine (e.g., 200 mg L-Theanine : 100 mg Caffeine)

6. APPLICATION AREAS

6.1. Dietary Supplements (Most Important Application)

Application Function Details
Stress Relief Supplement Relaxation and calm Promotes relaxation without causing drowsiness
Focus and Cognition Supplement Mental clarity Enhances attention, focus, and cognitive performance
Sleep Support Supplement Sleep quality Improves sleep quality; reduces time to fall asleep
Mood Support Emotional balance Supports positive mood and emotional well-being
Pre-workout Supplement Focus enhancement Combines with caffeine for pre-workout focus
Stress Management Cortisol reduction Reduces stress-induced cortisol spikes
Neuroprotection Brain health Protects against neurodegenerative conditions

6.2. Functional Beverages

Application Function Details
Energy Drinks Synergistic focus Combined with caffeine for enhanced focus and reduced jitteriness
Tea Beverages Natural component Naturally occurring in green and black tea
RTD Relaxation Drinks Calming effect Promotes relaxation in beverage format
Pre-workout Drinks Focus and energy Enhances mental focus during exercise
Sleep Drinks Sleep support Supports healthy sleep patterns

6.3. Food Products

Application Function Details
Functional Confectionery Relaxation support Gummies, chocolates, mints
Nutritional Bars Calming energy Energy bars, protein bars
Functional Dairy Relaxation Yogurts, protein shakes

6.4. Research and Development

Application Function Details
Neuroscience Research Neurotransmitter studies Mechanisms of action in neurological research
Psychopharmacology CNS effects Effects on cognitive function and mood
Clinical Studies Therapeutic potential New therapeutic applications discovery
Nutritional Research Dietary supplementation Health benefits research

7. DOSAGE AND USAGE RECOMMENDATIONS

Application Recommended Daily Dosage Note
Relaxation and Stress Relief 100 – 200 mg Single dose
Focus and Cognition 100 – 250 mg With or without caffeine
Sleep Support 200 – 400 mg Evening dose
Pre-workout 100 – 200 mg Combined with caffeine
General Supplementation 100 – 400 mg Divided doses

Synergy with Caffeine:

L-Theanine Caffeine Effect
100 mg 50 mg Mild focus enhancement
200 mg 100 mg Optimal focus with calm alertness
200 mg 150 mg Strong focus, minimal jitteriness
400 mg 200 mg Maximum synergistic effect

Note: Safe doses up to 1,000 mg/day have been studied. Medical conditions require physician consultation.

8. BIOAVAILABILITY AND METABOLISM

Parameter Information
Oral Bioavailability High (~90% absorption)
Blood-Brain Barrier Penetration Yes (via LAT1 transporter)
Plasma Peak Time (Tmax) ~1-2 hours
Half-Life (t½) ~1-1.5 hours
Elimination Route Renal excretion (urine)
Metabolism Liver metabolism, hydrolysis to glutamic acid and ethylamine
Metabolites L-Glutamic acid, ethylamine, L-glutamine
Receptor Binding AMPA, NMDA, GABA-A, GABA-B receptors

9. SAFETY AND TOXICOLOGY

Parameter Value
Acute Oral Toxicity (LD50, Rat) > 5,000 mg/kg (very low toxicity)
Acute Dermal Toxicity > 2,000 mg/kg
Skin Irritation Not an irritant
Eye Irritation Mild irritant
Inhalation Dust may cause respiratory irritation
Carcinogenicity Not classified as a carcinogen
Mutagenicity Not mutagenic
Reproductive Toxicity No significant toxicity observed
Genotoxicity Negative
GRAS Status Generally Recognized as Safe
Acceptable Daily Intake No specified limit; safe at typical intake levels

Tolerability:

  • Well tolerated at doses up to 1,000 mg/day

  • No known serious side effects

  • Mild effects: occasional headache, gastrointestinal discomfort (high doses)

  • No sedative effects at normal doses

  • Safe for long-term use

10. GHS CLASSIFICATION

Hazard Class Category H-Statement
No significant hazard classification

Signal Word: None

Hazard Pictograms: None

Hazard Statements: No H-codes

11. PRECAUTIONARY STATEMENTS (P-CODES)

Code Statement
P261 Avoid breathing dust
P264 Wash hands thoroughly after handling
P271 Use only in well-ventilated areas
P280 Wear protective gloves/eye protection/face protection
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
P337+P313 If eye irritation persists: Get medical advice/attention
P501 Dispose of contents/container in accordance with local regulations

12. FIRST AID MEASURES

Route of Exposure Action to Be Taken
Inhalation Move to fresh air. If symptoms persist, seek medical attention
Skin Contact Wash with plenty of soap and water
Eye Contact Rinse thoroughly with plenty of water for at least 15 minutes. Remove contact lenses. If irritation persists, seek medical attention
Ingestion Rinse mouth. Drink plenty of water. If large amount is swallowed, seek medical attention

13. STORAGE AND SHELF LIFE

Parameter Condition
Storage Conditions Store in a cool, dry, light-protected environment
Container Requirements Keep in original packaging, protected from moisture
Light Protection Light-proof packaging recommended
Moisture Protection Keep away from high humidity; silica gel recommended
Temperature Room temperature (15-25°C)
Shelf Life 24 months in unopened original packaging under proper storage conditions
After Opening Reseal tightly; use within 6 months

14. PACKAGING OPTIONS

Packaging Type Quantity Material
Aluminum Foil Bag 1 kg, 5 kg, 10 kg Light-proof, moisture-proof
Fiber Drum 25 kg PE-lined, moisture-proof
Small HDPE Containers 10 g, 50 g, 100 g, 500 g Moisture-proof, light-proof
Vacuum Packaging Custom sizes Moisture and oxygen barrier

15. TRANSPORT INFORMATION

Parameter Information
UN Number Not applicable (not dangerous goods)
Hazard Class Not applicable
Packing Group Not applicable
ADR/RID Not regulated
IMDG Not regulated
IATA Not regulated
Transport Temperature Ambient; protect from moisture and heat

16. REGULATORY STATUS

Region / Authority Status
USA (FDA) GRAS (Generally Recognized as Safe)
European Union (EFSA) Novel food approved; EU 2022/2443
Turkey Can be used as dietary supplement raw material
Japan Approved as food ingredient
Canada Approved as health ingredient
China Approved as food ingredient
Australia/New Zealand Approved as food ingredient
Korea Approved as food ingredient

17. NATURAL SOURCES

Source L-Theanine Content
Green Tea (Camellia sinensis) 1-3% dry weight
Black Tea 0.5-1.5% dry weight
White Tea 1-2% dry weight
Oolong Tea 0.5-1.5% dry weight
Matcha 1-3% dry weight
Gyokuro Tea 1-3% dry weight

18. ENVIRONMENTAL INFORMATION

Parameter Information
Biodegradability Readily biodegradable
Aquatic Toxicity Low toxicity
Bioaccumulation Not expected
Environmental Precautions Avoid large releases into water bodies

19. OTHER NAMES AND SYNONYMS

  • L-Theanine

  • L-Glutamic acid γ-ethylamide

  • L-γ-Glutamylethylamide

  • N-Ethyl-L-glutamine

  • Theanine

  • Tea Amino Acid

  • L-Theanine (INCI)

  • Suntheanine® (Trademark)

20. QUICK REFERENCE TABLE

Property Value
CAS Number 3081-61-6
Molecular Formula C₇H₁₄N₂O₃
Molecular Weight 174.20 g/mol
Appearance White to off-white crystalline powder
Purity ≥ 98.0%
Melting Point 195 – 205 °C
Solubility (Water) ~13 g/L (25°C)
pH (1% solution) 5.0 – 6.0
Optical Rotation [α]D20 = -8.0° to -10.0°
Bioavailability ~90%
Plasma Half-Life ~1-1.5 hours
Shelf Life 24 months
FDA Status GRAS
GHS Signal Word None
UN Number Not applicable

21. CRITICAL NOTICES AND BEST PRACTICES

CRITICAL NOTICES:

  1. Moisture Sensitivity: L-Theanine has moderate moisture sensitivity; high humidity may cause caking. Keep in moisture-proof packaging.

  2. Light Sensitivity: Moderate light sensitivity; protect from direct sunlight and UV light.

  3. Temperature Stability: Stable at room temperature; decompose above 205°C.

  4. Caffeine Synergy: L-Theanine works synergistically with caffeine. The 2:1 ratio (L-Theanine:Caffeine) is optimal for focus and reduced jitteriness.

  5. Dosage Considerations: Well tolerated at doses up to 1,000 mg/day. Mild gastrointestinal discomfort may occur at very high doses.

  6. Non-Sedative: L-Theanine promotes relaxation without causing drowsiness at standard doses.

  7. Drug Interactions: Caution with blood pressure medications due to mild blood pressure-lowering effects.

BEST PRACTICE RECOMMENDATIONS:

Storage:

  • Store in a cool, dry, light-protected environment

  • Use light-proof, moisture-proof packaging

  • Store at room temperature (15-25°C)

  • Reseal immediately after opening

Formulation:

  • Can be used in capsules, tablets, powders, or liquid formulations

  • Freely soluble in water; suitable for beverages

  • Stable in acidic environments

  • Compatible with most food ingredients

  • Synergistic with caffeine and GABA

Handling:

  • Use dust mask, protective goggles, and gloves

  • Avoid dust formation

  • Use in well-ventilated areas

  • Wash hands after handling

Waste Management:

  • Dispose in accordance with local regulations

  • Avoid release into the environment

Dosage:

  • Daily dose: 100-400 mg (general supplementation)

  • Relaxation: 100-200 mg

  • Sleep support: 200-400 mg

  • Focus: 100-250 mg with caffeine

  • Medical conditions require physician consultation

LEGAL DISCLAIMER

This Technical Data Sheet (TDS) is for informational purposes only and is prepared based on available technical data. The user is solely responsible for determining the suitability of the product for their specific application and for complying with all local, national, and international regulations. For complete safety, storage, handling, transport, waste, and regulatory compliance information, the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier must be consulted. This document does not substitute professional advice. Dosage and application conditions should be optimized through product-specific trials. Regulatory status of L-Theanine may vary by country; verify compliance before use. Medical conditions require consultation with a healthcare professional.

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