Pharmaceutical Grade
Lisdexamfetamine
CAS Number
608137-32-2
Molecular Formula
C₁₅H₂₅N₃O
Molecular Weight
263.38 g/mol
Purity
≥99.0%
Appearance
White powdery solid
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Product Description
Lisdexamfetamine, commonly known by its brand name Vyvanse, is a prodrug of dextroamphetamine. It is composed of d-amphetamine covalently linked to the amino acid L-lysine via an amide bond. This unique structure ensures that the drug remains inactive until it is metabolized in the body. Upon oral administration, lisdexamfetamine is enzymatically cleaved, primarily in red blood cells, to release the active component d-amphetamine, which acts as a central nervous system stimulant. This mechanism provides a smoother onset and offset, a longer duration of effect (typically 10-14 hours), and reduced potential for abuse compared to other stimulants like Adderall. Lisdexamfetamine is approved for the treatment of attention-deficit/hyperactivity disorder (ADHD) in children and adults and binge eating disorder (BED) in adults. Recent studies have also explored its potential for improving cognitive functions such as visual discrimination and cognitive flexibility in rats, as well as its efficacy in managing fatigue in patients with multiple sclerosis, although results in the latter area have been mixed.
Note: The Lisdexamfetamine raw materials produced by our company are only used for scientific research and cannot be taken directly or used as a substitute for medicine.
Uses
- Approved Uses: Treatment of Attention-Deficit/Hyperactivity Disorder (ADHD) in children and adults (FDA approved 2007; Health Canada 2009); moderate to severe Binge Eating Disorder (BED) in adults (FDA approved 2015). First chemically formulated prodrug stimulant (PubChem JSON, DrugBank).
- Off-Label/Reported Uses: Resolution of urge urinary incontinence in ADHD patients (case report: complete resolution in a 50-year-old woman with ADHD, ASD, and cPTSD after 40 mg dose). Adjunct to psychological interventions for BED. Potential neuroregulatory effect on central bladder control (urinary incontinence case report PDF).
- Other Contexts: Laboratory and industrial use only (not for household use); for ADHD in neurodiverse populations (e.g., with ASD or cPTSD) (SDS PDF, case reports).
Chemical Properties
- Chemical Name/Formula: (2S)-2,6-Diamino-N-[(1S)-1-methyl-2-phenylethyl]hexanamide; also known as (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide. Molecular formula: C₁₅H₂₅N₃O.
- CAS Number: 608137-32-2 (SDS PDF).
- EC Number: Not specified.
- Record Type/ID: PubChem CID 11597698; Record Title: Lisdexamfetamine.
- Purity/Composition: ≈99% (as an API standard); primary ingredient is Lisdexamfetamine.
- Structure:
- 2D Structure: Computationally generated two-dimensional depiction, standardized for consistency (PubChem).
- 3D Structure: Computed conformer model (not experimentally determined), aimed at protein-bound structures.
- Synonyms/Other Names: Lisdexamfetamine (INN); H645GUL8KJ; (2S)-2,6-DIAMINO-N-[(1S)-1-METHYL-2-PHENYLETHYL]HEXANAMIDE DIMETHANESULFONATE; Lisdexamphetamine.
Physical Properties
- Appearance/Form: Solid or powder.
- Stability: Store tightly closed in a dry, cool, well-ventilated place; avoid incompatible materials or foodstuff containers.
Pharmacological Properties
- Classification: Amino acid amide (ChEBI); Central Nervous System (CNS) Stimulant (DrugBank, FDA Pharm Classes, MeSH); Dopamine Uptake Inhibitor (MeSH); Anatomical Therapeutic Chemical (ATC) classification: N06BA12 (WHO ATC); Target-based: Dopamine and norepinephrine reuptake inhibitor (KEGG).
- Mechanism of Action: Prodrug of dextroamphetamine (d-amphetamine), covalently attached to L-lysine. Hydrolyzed in blood to active d-amphetamine, which crosses the blood-brain barrier. Blocks dopamine and norepinephrine reuptake, increasing their levels in extraneuronal space. Enhances synaptic dopamine, noradrenaline, and serotonin transmission. Modulates central bladder control via noradrenergic and dopaminergic circuits (e.g., pontine micturition center). Physiologic effect: CNS stimulation.
- Pharmacokinetics: Converted to dextroamphetamine via cleavage of lysine group; facilitates release of catecholamines (noradrenaline, dopamine) from nerve terminals; inhibits uptake in mesocorticolimbic system.
- Therapeutic Effects: Reduces binge eating episodes; improves executive function, attention, focus/concentration, affect regulation, and emotional dysregulation. May resolve urge urinary incontinence (case report). Associated with weight loss in some patients.
- Side Effects/Adverse Events: Insomnia/sleep disturbances; tolerance to effects; "crashing" (loss of energy in afternoon/evening); return of binge eating in evening; weight gain (in some cases); dry mouth; jitteriness; upper respiratory tract infections; emotional blunting; short duration of efficacy at lower doses. Higher doses (50-70 mg/day) linked to more side effects like sleep disorders. Abuse potential at non-approved high doses.
- Overdose Effects: Can cause Takotsubo Syndrome (TTS), cardiogenic shock, acute decompensated heart failure, hypoxemic respiratory failure, pulseless electrical activity cardiac arrest, severe LV/RV dysfunction, QT prolongation, and multiorgan failure (e.g., liver injury). May require VA-ECMO, intra-aortic balloon pump, and mechanical ventilation. Exacerbated by genetic factors like FLNC truncating variants.
- Interactions/Contraindications: Not recommended for patients with genetic susceptibilities (e.g., FLNC haploinsufficiency, which may predispose to dilated cardiomyopathy or TTS). Risk of abuse similar to d-amphetamine.
- Dosing: Typically 30-70 mg/day for ADHD/BED; titrated based on response (e.g., started at 30 mg, increased to 40-50 mg in case reports). Overdose example: 600 mg.
Safety and Hazards
- Primary Hazards: Flammable; Acute Toxic; Health Hazard.
- Exposure Risks: No occupational exposure limits; avoid inhalation, ingestion, skin contact. May cause irritation if inhaled/ingested/contacted with skin/eyes.
- First-Aid Measures: Inhalation: Move to fresh air, give oxygen/artificial respiration if needed. Skin: Wash with soap/water. Eyes: Rinse with water for 15 minutes. Ingestion: Rinse mouth, do not induce vomiting.
- Fire-Fighting Measures: Use dry chemical, CO2, or alcohol-resistant foam. No specific hazards from the chemical.
- Handling and Storage: Handle in well-ventilated area; wear protective equipment (gloves, goggles); avoid sparks/ignition sources; store away from incompatibles.
- Personal Protection: Eye/face: Safety goggles (EN 166/NIOSH). Skin: Impervious clothing/gloves (EN 374). Respiratory: Avoid breathing dust/vapors.
- Environmental Precautions: Prevent spillage/leakage into drains; collect for disposal.
- Other: Schedule I controlled substance (risk of abuse); monitor for tolerance and side effects. Genetic testing recommended in overdose/TTS cases (e.g., FLNC variants).
Biological and Toxicological Information
- Toxicity: No data on acute/chronic toxicity, biological limits, or carcinogenicity. Potential for TTS and cardiogenic shock in overdose, especially with genetic predispositions (e.g., FLNC truncating variant leading to haploinsufficiency and dilated cardiomyopathy).
- Biological Effects: Modulates CNS; impacts urinary continence via noradrenergic/dopaminergic pathways (e.g., pontine micturition center, locus coeruleus). May influence bladder storage/voiding.
Patient Perceptions and Clinical Outcomes
- Efficacy Ratings: On Drugs.com (BED patients): Median rating 9/10 (high efficacy linked to reduced binge eating, improved focus, weight loss; low efficacy linked to tolerance, insomnia, evening binge return, crashing, weight gain). 85% report at least one adverse event.
- Thematic Insights from Reviews: Positive: Improved binge outcomes, focus, weight loss. Negative: Insomnia, tolerance, evening symptom return. No prior data on LDX modulating continence.
- Case-Specific Outcomes: Resolved urge incontinence in ADHD/ASD/cPTSD patient. TTS with VA-ECMO need in overdose with FLNC variant; genetic implications for diagnosis/prognosis.