LISDEXAMFETAMINE

First marketed in 1937

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H25N3O
Molecular Weight	263.3785
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VOBHXZCDAVEXEY-JSGCOSHPSA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H25N3O
Molecular Weight	263.3785
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017078s048lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021977lbl.pdf | https://www.drugs.com/ppa/lisdexamfetamine.html | https://www.ncbi.nlm.nih.gov/pubmed/27125257

Lisdexamfetamine (LDX) is a d-amphetamine (d-AMPH) pro-drug used to treat Attention Deficit and Hyperactivity Disorder (ADHD) and Binge Eating Disorder (BED). After oral administration, lisdexamfetamine dimesylate is rapidly absorbed from the gastrointestinal tract and converted to dextroamphetamine, which is responsible for the drug’s activity. Amphetamines are thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron and increase the release of these monoamines into the extraneuronal space. Most common adverse reactions in children, adolescents and/or adults with ADHD were anorexia, anxiety, decreased appetite, decreased weight, diarrhea, dizziness, dry mouth, irritability, insomnia, nausea, upper abdominal pain, and vomiting. Agents that alter urinary pH can alter blood levels of amphetamine. Acidifying agents decrease amphetamine blood levels, while alkalinizing agents increase amphetamine blood levels. Needs to adjust Lisdexamfetamine dosage accordingly.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
catecholamine secretion 14 Target ID: GO:0050432 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021977lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/28376679	Modulator 822
Norepinephrine transporter 190 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17239355	Modulator 822
Synaptic vesicular amine transporter 56 Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7751968	Inhibitor 8228
Dopamine transporter 179 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19244097	Modulator 822

Conditions

Condition	Modality	Highest Phase	Product
Attention deficit hyperactivity disorder 68 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf	Primary	Approved 8360	VYVANSE Approved Use VYVANSE® is indicated for the treatment of: Attention Deficit Hyperactivity Disorder (ADHD) [see Clinical Studies (14.1) Launch Date 1.17218882E12
Moderate to severe binge eating disorder 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf	Primary	Approved 8360	VYVANSE Approved Use VYVANSE® is indicated for the treatment of: Attention Deficit Hyperactivity Disorder (ADHD) [see Clinical Studies (14.1) Launch Date 1.17218882E12
Attention deficit hyperactivity disorder 68 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017078s048lbl.pdf	Primary	Approved 8360	DEXEDRINE Approved Use Narcolepsy. Attention Deficit Disorder with Hyperactivity. As an integral part of a total treatment program that typically includes other measures (psychological, educational, social) for patients (ages 6 years to 16 years) with this syndrome. A diagnosis of Attention Deficit Hyperactivity Disorder (ADHD; DSM-IV) implies the presence of the hyperactive-impulsive or inattentive symptoms that caused impairment and were present before age 7 years. The symptoms must cause clinically significant impairment, e.g., in social, academic, or occupational functioning, and be present in 2 or more settings, e.g., school (or work) and at home. The symptoms must not be better accounted for by another mental disorder. For the Inattentive Type, at least 6 of the following symptoms must have persisted for at least 6 months: lack of attention to details/careless mistakes; lack of sustained attention; poor listener; failure to follow through on tasks; poor organization; avoids tasks requiring sustained mental effort; loses things; easily distracted; forgetful. For the Hyperactive-Impulsive Type, at least 6 of the following symptoms must have persisted for at least 6 months: fidgeting/squirming; leaving seat; inappropriate running/climbing; difficulty with quiet activities; “on the go”; excessive talking; blurting answers; can't wait turn; intrusive. The Combined Type requires both inattentive and hyperactive-impulsive criteria to be met. Launch Date 3.15532804E11

C_max

Value	Dose	Analyte	Population
47.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18021493/	70 mg 1 times / day multiple, oral dose: 70 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LISDEXAMFETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
24.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
36.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/040361Orig1s017lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
60.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18021493/	70 mg 1 times / day multiple, oral dose: 70 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LISDEXAMFETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
431 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18021493/	70 mg 1 times / day multiple, oral dose: 70 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LISDEXAMFETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/040361Orig1s017lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
70 mg 1 times / day multiple, oral (max) Recommended Dose: 70 mg, 1 times / day Route: oral Route: multiple Dose: 70 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	unhealthy, 13 - 17 n = 233 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorder Age Group: 13 - 17 Sex: M+F Population Size: 233 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	Disc. AE: Irritability, Decreased appetite... AEs leading to discontinuation/dose reduction: Irritability (1.3%) Decreased appetite (0.86%) Insomnia (0.86%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8
1200 mg single, oral Overdose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/30730334 Page: e771	healthy, 17 n = 1 Health Status: healthy Age Group: 17 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30730334 Page: e771	Disc. AE: Delirium, Tachycardia... AEs leading to discontinuation/dose reduction: Delirium (acute) Tachycardia Hypertension Tachypnea Creatine kinase increased (mild) Sources: https://pubmed.ncbi.nlm.nih.gov/30730334 Page: e771
70 mg 1 times / day multiple, oral (max) Recommended Dose: 70 mg, 1 times / day Route: oral Route: multiple Dose: 70 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	unhealthy, 18 - 55 n = 358 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorder Age Group: 18 - 55 Sex: M+F Population Size: 358 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	Disc. AE: Insomnia, Tachycardia... AEs leading to discontinuation/dose reduction: Insomnia (2%) Tachycardia (1%) Irritability (1%) Hypertension (1%) Headache (1%) Anxiety (1%) Dyspnea (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8
70 mg 1 times / day multiple, oral (max) Recommended Dose: 70 mg, 1 times / day Route: oral Route: multiple Dose: 70 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	unhealthy, 6 - 12 n = 218 Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorder Age Group: 6 - 12 Sex: M+F Population Size: 218 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8	Disc. AE: Ventricular hypertrophy, Tic... AEs leading to discontinuation/dose reduction: Ventricular hypertrophy (1%) Tic (1%) Vomiting (1%) Psychomotor hyperactivity (1%) Insomnia (1%) Rash (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.8
30 mg 1 times / day steady, oral Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00735371	unhealthy, adolescents n = 78 Health Status: unhealthy Condition: Attention-Deficit/Hyperactivity Disorder Age Group: adolescents Population Size: 78 Sources: https://clinicaltrials.gov/ct2/show/NCT00735371	Other AEs: Decreased appetite, Insomnia... Other AEs: Decreased appetite (below serious, 29 patients) Insomnia (below serious, 7 patients) Weight decreased (below serious, 3 patients) Irritability (below serious, 6 patients) Fatigue (below serious, 4 patients) Nasopharyngitis (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00735371
20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	healthy, adult n = 27 Health Status: healthy Condition: Acute Sleep Loss Age Group: adult Sex: M Population Size: 27 Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	Other AEs: Nausea... Other AEs: Nausea (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT01096680
50 mg single, oral Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	healthy, adult n = 27 Health Status: healthy Condition: Acute Sleep Loss Age Group: adult Sex: M Population Size: 27 Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	Other AEs: Headache, Nausea... Other AEs: Headache (below serious, 4 patients) Nausea (below serious, 1 patient) Vomiting (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01096680
70 mg single, oral Dose: 70 mg Route: oral Route: single Dose: 70 mg Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	healthy, adult n = 27 Health Status: healthy Condition: Acute Sleep Loss Age Group: adult Sex: M Population Size: 27 Sources: https://clinicaltrials.gov/ct2/show/NCT01096680	Other AEs: Headache, Nausea... Other AEs: Headache (below serious, 2 patients) Nausea (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01096680
70 mg 1 times / day steady, oral (max) Dose: 70 mg, 1 times / day Route: oral Route: steady Dose: 70 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01101022	unhealthy, adult n = 79 Health Status: unhealthy Condition: Attention-Deficit/Hyperactivity Disorder Age Group: adult Population Size: 79 Sources: https://clinicaltrials.gov/ct2/show/NCT01101022	Other AEs: Diarrhea, Dry mouth... Other AEs: Diarrhea (below serious, 6 patients) Dry mouth (below serious, 25 patients) Fatigue (below serious, 6 patients) Feeling jittery (below serious, 10 patients) Irritability (below serious, 8 patients) Upper respiratory tract infection (below serious, 5 patients) Heart rate increased (below serious, 4 patients) Weight decreased (below serious, 8 patients) Anorexia (below serious, 4 patients) Decreased appetite (below serious, 26 patients) Headache (below serious, 20 patients) Initial insomnia (below serious, 8 patients) Insomnia (below serious, 10 patients) Libido decreased (below serious, 4 patients) Hyperhidrosis (below serious, 5 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01101022
70 mg 1 times / day multiple, oral Recommended Dose: 70 mg, 1 times / day Route: oral Route: multiple Dose: 70 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Attention Deficit Hyperactivity Disorder\|Binge Eating Disorder Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.1	Disc. AE: Abuse, Dependence... AEs leading to discontinuation/dose reduction: Abuse Dependence Cardiovascular disorder (NOS) (grade 3-5) Stroke (serious) Myocardial infarction (serious) Blood pressure increased Heart rate increased Psychiatric symptom NOS Psychotic symptom Manic symptom Growth suppression Vascular disorders Raynaud's phenomenon Serotonin syndrome Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208510lbl.pdf Page: p.1
50 mg 1 times / day steady, oral (max) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01148979	unhealthy n = 28 Health Status: unhealthy Condition: Major Depressive Disorder Population Size: 28 Sources: https://clinicaltrials.gov/ct2/show/NCT01148979	Other AEs: Decreased appetite, Dry mouth... Other AEs: Decreased appetite (below serious, 8 patients) Dry mouth (below serious, 7 patients) Insomnia (below serious, 10 patients) Irritability (below serious, 3 patients) Diaphoresis (below serious, 2 patients) Libido decreased (below serious, 2 patients) Tinnitus (below serious, 2 patients) Muscle tension (below serious, 4 patients) Tachycardia (below serious, 3 patients) Paresthesia (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01148979

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1579	inhibitor 1752	substrate 1193 inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2A6 704 CYP2B6 799 CYP2C19 1463	CYP 266

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4	likely
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 87.3 uM]
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 89 uM]
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 90 uM]
CYP2B6 985	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 90.8 uM]
CYP3A4 1909	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 92.1 uM]
CYP2A6 736	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 92.5 uM]
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf Page: 7, 78	no [Inhibition 94.2 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1193	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4 Page: 4.0	likely		likely (co-administration study) Comment: Amphetamines and amphetamine derivatives are known to be metabolized, to some degree, by cytochrome P450 2D6 (CYP2D6) and display minor inhibition of CYP2D6 metabolism; concomitant use of DEXEDRINE and CYP2D6 inhibitors may increase the exposure of DEXEDRINE; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4 Page: 4.0
CYP 266	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021977s034,208510s002lbl.pdf Page: 21.0	no

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00E9T8
AA Blocks	AA00DRV1	https://www.aablocks.com/goods/Goods/detail?id=AA00DRV1
Alfa Chemistry	ACM608137333
Angene	AGN-PC-0WH4QC
Aurora Fine Chemicals LLC	A17.876.402	http://online.aurorafinechemicals.com/info?ID=A17.876.402
Aurora Fine Chemicals LLC	K16.670.581	http://online.aurorafinechemicals.com/info?ID=K16.670.581
Avantor Inc	101096-690	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-690
Avantor Inc	75835-260	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
BioCrick	BCC5942	http://www.biocrick.com/D-Amphetamine-sulfate-BCC5942.html
Cayman Chemical	18050
ChemMol	44007218	http://www.chemmol.com/chemmol/44007218.html
Compound Cloud	11597697
Compound Cloud	11597698
LGC Standards	LGCFOR1359.00	https://www.lgcstandards.com/US/en/p/LGCFOR1359.00
LGC Standards	MM1359.00	https://www.lgcstandards.com/US/en/p/MM1359.00
MolPort	MolPort-046-693-343
Parchem	16880	http://www.parchem.com/chemical-supplier-distributor/DITAB-006880.aspx
Sigma Aldrich	L-026
Sigma Aldrich	L-026\|CERILLIAN
Sigma-Aldrich	A3278_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/a3278?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A5880_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a5880?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1180004_USP	https://www.sigmaaldrich.com/catalog/product/usp/1180004?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S525797	http://www.smolecule.com/products/s525797
THE BioTek	bt-267390	https://www.thebiotek.com/product/inhibitors/bt-267390
THE BioTek	bt-386638	https://www.thebiotek.com/product/others/bt-386638
Tocris	2813	https://www.tocris.com/products/d-amphetamine-sulfate_2813
Toronto Research Chemicals	KIT2550
Toronto Research Chemicals	L468880
Toronto Research Chemicals	L468885
ZINC	ZINC000011680943	http://zinc15.docking.org/substances/ZINC000011680943
iChemical	EBD10545	http://www.ichemical.com/chemicals/cas-608137-33-3
iChemical	EBD2638102	http://www.ichemical.com/products/51-63-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-1818516035
mcule	MCULE-7002483605

PubMed

Title	Date	PubMed
Agonist and antagonist activity of low efficacy D2 dopamine receptor agonists in rats discriminating d-amphetamine from saline.	1992 Dec	11224162
Effect of amphetamine on the expression of the metabotropic glutamate receptor 5 mRNA in developing rat brain.	2000 Dec	11303782
Dopaminergic mRNA expression in the intact substantia nigra of unilaterally 6-OHDA-lesioned and grafted rats: an in situ hybridization study.	2001	11314769
Stimulation of metabotropic but not ionotropic glutamatergic receptors in the nucleus accumbens is required for the D-amphetamine-induced release of functional dopamine.	2001	11246154
No functional effects of embryonic neuronal grafts on motor deficits in a 3-nitropropionic acid rat model of advanced striatonigral degeneration (multiple system atrophy).	2001	11226695
Anorectic drugs and pulmonary hypertension from the bedside to the bench.	2001 Apr	11307870
Resolution of stroke deficits following contralateral grafts of conditionally immortal neuroepithelial stem cells.	2001 Apr	11283405
Determination of amphetamine in dog plasma by gas chromatography with mass selective detection.	2001 Apr	11268050
A nitric oxide-dopamine link pathway in organum vasculosum laminae terminalis of rat brain exerts control over blood pressure.	2001 Apr	11264246
Effect of 6-hydroxydopamine or repeated amphetamine treatment on mesencephalic mRNA levels for AMPA glutamate receptor subunits in the rat.	2001 Apr 20	11290405
Nicotine sensitization increases dendritic length and spine density in the nucleus accumbens and cingulate cortex.	2001 Apr 27	11311869
Interleukin-2 potentiates novelty- and GBR 12909-induced exploratory activity.	2001 Apr 27	11311862
Neural mechanisms of motion sickness.	2001 Feb	11286016
Differences in locomotor response to an inescapable novel environment predict sensitivity to aversive effects of amphetamine.	2001 Feb	11270513
Effects of acute D-amphetamine and ketamine on the performance of rats in a serial negative patterning procedure.	2001 Feb	11270512
The D3R partial agonist, BP 897, attenuates the discriminative stimulus effects of cocaine and D-amphetamine and is not self-administered.	2001 Feb	11270507
Chronic inositol increases striatal D(2) receptors but does not modify dexamphetamine-induced motor behavior. Relevance to obsessive-compulsive disorder.	2001 Feb	11267629
Transcranial magnetic stimulation in an amphetamine hyperactivity model of mania.	2001 Feb	11256461
Comparison of the effects of infant handling, isolation, and nonhandling on acoustic startle, prepulse inhibition, locomotion, and HPA activity in the adult rat.	2001 Feb	11256454
Conditioned activity to amphetamine in transgenic mice expressing an antisense RNA against the glucocorticoid receptor.	2001 Feb	11256444
Drugs used in the treatment of attention-deficit/hyperactivity disorder affect postsynaptic firing rate and oscillation without preferential dopamine autoreceptor action.	2001 Feb 15	11239905
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry.	2001 Feb 25	11236083
Schedule-dependent effects of haloperidol and amphetamine: multiple-schedule task shows within-subject effects.	2001 Jan	11274708
Acute hydrocortisone administration does not affect subjective responses to d-amphetamine in humans.	2001 Jan	11271411
Modification of d-amphetamine-induced responses by baclofen in rats.	2001 Jan	11271399
[Analysis of the striato-pallidal interactions in regulation of avoidance behavior].	2001 Jan	11227866
Neonatal dexamethasone on day 7 in rats causes behavioral alterations reflective of hippocampal, but not cerebellar, deficits.	2001 Jan-Feb	11274876
Developmental exposure to methylmercury alters behavioral sensitivity to D-amphetamine and pentobarbital in adult rats.	2001 Jan-Feb	11274875
Computer-aided screening for hallucinogenic and stimulant amphetamines with gas chromatography-Fourier transform infrared spectroscopy (GC-FTIR).	2001 Jan-Feb	11216000
The weaver mutant mouse: a model to study the ontogeny of dopamine transmission systems and their role in drug addiction.	2001 Jun	11240309
Entopeduncular lesions facilitate and thalamic lesions depress spontaneous and drug-evoked motor behavior in the hemiparkinsonian rat.	2001 Jun 1	11304759
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.	2001 Mar	11300514
Effects of d-amphetamine on the performance of rats in an animal analogue of the A-X continuous performance test.	2001 Mar	11277604
Differential sensitivity to NaCl for inhibitors and substrates that recognize mutually exclusive binding sites on the neuronal transporter of dopamine in rat striatal membranes.	2001 Mar	11248372
Adrenergic hyperactivity and metanephrine excess in the nucleus accumbens after prefrontocortical dopamine depletion.	2001 Mar	11247995
Acute myocardial infarction associated with amphetamine use.	2001 Mar	11243281
Amphetamine selectively blocks inhibitory glutamate transmission in dopamine neurons.	2001 Mar	11224544
Previous exposure to amphetamine enhances the subsequent locomotor response to a D1 dopamine receptor agonist when glutamate reuptake is inhibited.	2001 Mar 1	11222671
Dopaminergic role in stimulant-induced wakefulness.	2001 Mar 1	11222668
Sexual behavior induction of c-Fos in the nucleus accumbens and amphetamine-stimulated locomotor activity are sensitized by previous sexual experience in female Syrian hamsters.	2001 Mar 15	11245696
Dissociations between the effects of intra-accumbens administration of amphetamine and exposure to a novel environment on accumbens dopamine and cortical acetylcholine release.	2001 Mar 16	11251215
Serotonin transporter localization in the hamster suprachiasmatic nucleus.	2001 Mar 2	11222995
Amphetamine-stimulated cortical acetylcholine release: role of the basal forebrain.	2001 Mar 9	11245817
Glial cell line-derived neurotrophic factor (GDNF) gene delivery protects dopaminergic terminals from degeneration.	2001 May	11312561
Amphetamine normalizes the electrical activity of dopamine neurons in the ventral tegmental area following prenatal ethanol exposure.	2001 May	11303066
Chronic amphetamine exposure during the preweanling period does not affect avoidance learning or novelty-seeking of adult rats.	2001 May	11300739
The variable number of tandem repeats polymorphism of the dopamine transporter gene is not associated with significant change in dopamine transporter phenotype in humans.	2001 May	11282255
Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene.	2001 May 1	11312315
Genes in drug abuse.	2001 May 1	11295319
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Patents

Sample Use Guides

In Vivo Use Guide

Usual dose is 5 to 60 mg per day in divided doses, depending on the individual patient response. Narcolepsy seldom occurs in children under 12 years of age; however, when it does, DEXEDRINE may be used. The suggested initial dose for patients aged 6 to 12 is 5 mg daily; daily dose may be raised in increments of 5 mg at weekly intervals until an optimal response is obtained. In patients 12 years of age and older, start with 10 mg daily; daily dosage may be raised in increments of 10 mg at weekly intervals until an optimal response is obtained. If bothersome adverse reactions appear (e.g., insomnia or anorexia), dosage should be reduced. SPANSULE capsules may be used for once-a-day dosage wherever appropriate.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:40:49 UTC 2023` Edited by `admin` on `Wed Jul 05 23:40:49 UTC 2023`
Record UNII	H645GUL8KJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LISDEXAMFETAMINE

Official Name

English

Lisdexamfetamine [WHO-DD]

Common Name

English

L-LYSINE-DEXTROAMPHETAMINE

Common Name

English

LISDEXAMPHETAMINE

Common Name

English

lisdexamfetamine [INN]

Common Name

English

N-((1S)-1-METHYL-2-PHENYLETHYL)-L-LYSINAMIDE

Systematic Name

English

HEXANAMIDE, 2,6-DIAMINO-N-((1S)-1-METHYL-2-PHENYLETHYL)-, (2S)-

Systematic Name

English

(2S, 2'S)-2,6-DIAMINO-N-(1-PHENYLPROPAN-2-YL)HEXANAMIDE

Systematic Name

English

(2S)-2,6-DIAMINO-N-((1S)-1-METHYL-2-PHENYLETHYL)HEXANAMIDE

Systematic Name

English

LISDEXAMFETAMINE [VANDF]

Common Name

English

LISDEXAMFETAMINE [MI]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175739