Lisdexamfetamine (CED0005852)

Record Information

Version

1.0

Creation Date

2016-05-25 18:26:19 UTC

Update Date

2026-08-19 12:44:32 UTC

SynCED ID

CED0005852

Secondary Accession Numbers

CHEM022269

Identification

Common Name

Lisdexamfetamine

Class

Small Molecule

Description

Lisdexamfetamine is an organic compound with the formula C15H25N3O and an average molecular weight of 263.38 g/mol. Lisdexamfetamine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. It is used in healthcare, pharmaceuticals, and veterinary products as a psychostimulant, a nootropic, and an agent used for ADHD, with oral administration being the recorded route of exposure. Regarding its mechanism of action, the compound acts as an agonist of the protein target Trace amine-associated receptor 1 (TAAR1).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Lisdexamfetamine dimesylate	HMDB
NRP104	HMDB
Vyvanse	HMDB
Lis dexamfetamine dimesylate	HMDB
NRP 104	HMDB
Elvanse	HMDB
Lis-dexamfetamine dimesylate	HMDB
Dimesylate, lis-dexamfetamine	HMDB
Dimesylate, lisdexamfetamine	HMDB
NRP-104	HMDB

Chemical Formula

C₁₅H₂₅N₃O

Average Molecular Mass

263.379 g/mol

Monoisotopic Mass

263.200 g/mol

CAS Registry Number

608137-32-2

IUPAC Name

(2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide

Traditional Name

vyvanse

SMILES

C[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CCCCN

InChI Identifier

InChI=1S/C15H25N3O/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19)/t12-,14-/m0/s1

InChI Key

VOBHXZCDAVEXEY-JSGCOSHPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Amphetamine or derivatives
Phenylpropane
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

prodrug (PMC13471788 )?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.14	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	15.89	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.14 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	78.31 m³·mol⁻¹	ChemAxon
Polarizability	31.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0udi-7910000000-cf67fb00e86045c2e167	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01qa-1980000000-d55cfea0090eb8a203ec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-3910000000-6c0e093306cb1a142d27	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lr-9600000000-0319b363d14e7fb37bdb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0290000000-3d4c25de9940b1f84b65	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01sl-1940000000-934e79a23f532e705cd7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lu-4900000000-c557594a41309e8f3655	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0090000000-378898bcf4a9421cb8d5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ql-9780000000-45bb7d0848ffcb464b5b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9100000000-4e7bbad339ecdb03e6c4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0090000000-45f7796828e5f04a3c2f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01t9-6920000000-8183a8d18b1b49ca7221	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9100000000-7d80f02475e4b0ca64f3	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
1145.0 Log mg/kg [640:2000]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
hypertension	Associated With?	Not Available	A disorder characterized by a pathological increase in blood pressure; a repeatedly elevation in the blood pressure exceeding 140 over 90 mm Hg. (NCI CTCAE)	PMC8328933
insomnia	Associated With?	Not Available	A disorder characterized by difficulty in falling asleep and/or remaining asleep. (NCI CTCAE)	PMC8328933
attention deficit hyperactivity disorder	Not Available	Not Available	Not Available	PMC8884459
anorexia	Associated With?	Not Available	Not Available	PMC8328933
binge eating disorder	Not Available	Not Available	Not Available	PMC11742761

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000378	Psychostimulants, agents used for adhd and nootropics?Psychostimulants, including agents commonly prescribed for Attention Deficit Hyperactivity Disorder (ADHD) and nootropics, are synthetic chemicals that enhance cognitive function, attention, and alertness.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
CEDs000537	Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Lisdexamfetamine Dopamine Reuptake Inhibitor Action Pathway

Lisdexamfetamine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Solute carrier family 15 member 1	P46059	Humans	Predicted (SEA)	Prediction Confidence Score 0.483 Applicability Domain 0.545 Statistical Significance 1.20e-04 Supporting Reference Compounds 3 E-value 0.934191
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	Prediction Confidence Score 0.429 Applicability Domain 0.46 Statistical Significance 0.0165 Supporting Reference Compounds 532 E-value 128.373
Click to view 3D structure	Neprilysin	Q61391	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.426 Applicability Domain 0.545 Statistical Significance 4.50e-04 Supporting Reference Compounds 3 E-value 3.50322
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.426 Applicability Domain 0.46 Statistical Significance 0.0161 Supporting Reference Compounds 186 E-value 125.104
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.426 Applicability Domain 0.46 Statistical Significance 0.0151 Supporting Reference Compounds 166 E-value 117.241
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.425 Applicability Domain 0.46 Statistical Significance 0.0174 Supporting Reference Compounds 229 E-value 135.458
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.425 Applicability Domain 0.46 Statistical Significance 0.0129 Supporting Reference Compounds 164 E-value 100.659
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.418 Applicability Domain 0.46 Statistical Significance 0.015 Supporting Reference Compounds 199 E-value 116.696
Click to view 3D structure	Cytosol aminopeptidase	P00727	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.415 Applicability Domain 0.415 Statistical Significance 7.90e-04 Supporting Reference Compounds 1 E-value 6.15009
Click to view 3D structure	Aminopeptidase B	O09175	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.415 Applicability Domain 0.553 Statistical Significance 8.00e-05 Supporting Reference Compounds 8 E-value 0.622794
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	Prediction Confidence Score 0.402 Applicability Domain 0.46 Statistical Significance 0.0224 Supporting Reference Compounds 527 E-value 174.227
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	Prediction Confidence Score 0.397 Applicability Domain 0.435 Statistical Significance 0.0229 Supporting Reference Compounds 427 E-value 178.508
Click to view 3D structure	Proteasome component C5	P23724	Saccharomyces cerevisiae S288c	Predicted (SEA)	Prediction Confidence Score 0.394 Applicability Domain 0.394 Statistical Significance 0.001 Supporting Reference Compounds 1 E-value 8.17417
Click to view 3D structure	Mu-type opioid receptor	P42866	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.393 Applicability Domain 0.46 Statistical Significance 0.0097 Supporting Reference Compounds 107 E-value 75.6694
Click to view 3D structure	Aminopeptidase N	P15144	Humans	Predicted (SEA)	Prediction Confidence Score 0.389 Applicability Domain 0.469 Statistical Significance 0.0022 Supporting Reference Compounds 42 E-value 17.5161
Click to view 3D structure	Aminopeptidase N	P15145	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.388 Applicability Domain 0.415 Statistical Significance 0.0015 Supporting Reference Compounds 40 E-value 11.9109
Click to view 3D structure	Cytosol aminopeptidase	P28838	Humans	Predicted (SEA)	Prediction Confidence Score 0.387 Applicability Domain 0.431 Statistical Significance 6.70e-04 Supporting Reference Compounds 18 E-value 5.2159
Click to view 3D structure	Hyaluronan mediated motility receptor	O75330	Humans	Predicted (SEA)	Prediction Confidence Score 0.382 Applicability Domain 0.382 Statistical Significance 0.0036 Supporting Reference Compounds 1 E-value 27.87
Click to view 3D structure	Neprilysin	P08049	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.375 Applicability Domain 0.4 Statistical Significance 0.0028 Supporting Reference Compounds 34 E-value 21.8756
Click to view 3D structure	Angiotensin-converting enzyme	P12822	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.375 Applicability Domain 0.4 Statistical Significance 0.0015 Supporting Reference Compounds 26 E-value 11.7552
Click to view 3D structure	Neprilysin	P08473	Humans	Predicted (SEA)	Prediction Confidence Score 0.374 Applicability Domain 0.4 Statistical Significance 0.0023 Supporting Reference Compounds 51 E-value 17.5939
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	Prediction Confidence Score 0.373 Applicability Domain 0.459 Statistical Significance 0.0131 Supporting Reference Compounds 400 E-value 101.905
Click to view 3D structure	Procathepsin L	P07711	Humans	Predicted (SEA)	Prediction Confidence Score 0.373 Applicability Domain 0.433 Statistical Significance 0.0078 Supporting Reference Compounds 167 E-value 60.4888
Click to view 3D structure	Leukocyte surface antigen CD47	Q08722	Humans	Predicted (SEA)	Prediction Confidence Score 0.371 Applicability Domain 0.371 Statistical Significance 0.0079 Supporting Reference Compounds 1 E-value 61.5009
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	Prediction Confidence Score 0.37 Applicability Domain 0.459 Statistical Significance 0.0123 Supporting Reference Compounds 292 E-value 95.9102