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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N
Molecular Weight 135.2062
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVAMFETAMINE

SMILES

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

InChI

InChIKey=KWTSXDURSIMDCE-MRVPVSSYSA-N
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H13N
Molecular Weight 135.2062
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/levamfetamine.html | https://www.ncbi.nlm.nih.gov/pubmed/769722 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011522s040lbl.pdf | https://clinicaltrials.gov/ct2/show/NCT00468143 | https://clinicaltrials.gov/ct2/show/NCT00553319 | https://www.ncbi.nlm.nih.gov/pubmed/769722

LEVAMFETAMINE the levorotatory form of amphetamine. L-amphetamine, is a central nervous system (CNS) stimulant known to increase wakefulness and concentration in association with decreased appetite and fatigue. Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries. L-Amphetamine succinate was sold in Hungary between 1952 and 1955 under the brand name Cydril.

Originator

Sources: Helvetica Chimica Acta, Volume 34, Pages 2202-10, 1951

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.3 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PAREDRINE

Approved Use

ADDERALL® is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) and Narcolepsy.

Launch Date

1969
Primary
PAREDRINE

Approved Use

ADDERALL® is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) and Narcolepsy.

Launch Date

1969
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
16.4 ng/mL
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: DEXTROAMPHETAMINE
LEVAMFETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
14.6 ng/mL
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: DEXTROAMPHETAMINE
LEVAMFETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: HIGH-FAT
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
370.9 ng × h/mL
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: DEXTROAMPHETAMINE
LEVAMFETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
357.4 ng × h/mL
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: DEXTROAMPHETAMINE
LEVAMFETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: HIGH-FAT
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14.47 h
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: DEXTROAMPHETAMINE
LEVAMFETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
14.84 h
7.5 mg single, oral
dose: 7.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: DEXTROAMPHETAMINE
LEVAMFETAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: HIGH-FAT
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
82%
LEVAMFETAMINE plasma
Homo sapiens
PubMed

PubMed

TitleDatePubMed
Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.
2011-12-01
New approaches in the management of multiple sclerosis.
2010-11-24
Reasons for illicit drug use in people with schizophrenia: Qualitative study.
2010-11-22
Bis[2-(methyl-amino)-troponato]copper(II).
2010-11-06
Improvements in executive function correlate with enhanced performance and functioning and health-related quality of life: evidence from 2 large, double-blind, randomized, placebo-controlled trials in ADHD.
2010-09
Impurity profiling of dexamphetamine sulfate by cyclodextrin-modified microemulsion electrokinetic chromatography.
2010-09
Prenatal inflammation-induced hypoferremia alters dopamine function in the adult offspring in rat: relevance for schizophrenia.
2010-06-04
The mixed amphetamine salt extended release (Adderall XR, Max-XR) as an adjunctive to SSRIS or SNRIS in the treatment of adult ADHD patients with comorbid partially responsive generalized anxiety: an open-label study.
2010-06
New and extended-action treatments in the management of ADHD: a critical appraisal of lisdexamfetamine in adults and children.
2010-05-25
CE assay for simultaneous determination of charged and neutral impurities in dexamphetamine sulfate using a dual CD system.
2010-05
Peripheral vasculopathy associated with psychostimulant treatment in children with attention-deficit/hyperactivity disorder.
2010-04
Amphetamine treatment during early postnatal development transiently restricts somatic growth.
2010-03-27
Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis.
2009-12-05
National outbreak of Acanthamoeba keratitis associated with use of a contact lens solution, United States.
2009-08
The effects of L-amphetamine sulfate on cognition in MS patients: results of a randomized controlled trial.
2009-07
Cellular immune response to intrastriatally implanted allogeneic bone marrow stromal cells in a rat model of Parkinson's disease.
2009-06-05
Assessing susceptibility to age-related macular degeneration with proteomic and genomic biomarkers.
2009-06
Bis[tris-(4-fluoro-phen-yl)phosphine-κP](tropolonato-κO,O')copper(I).
2009-03-28
Neonatal amphetamine exposure and hippocampus-mediated behaviors.
2009-03
2-Isobutyl-2-phosphabicyclo-[3.3.1]nonane 2-selenide.
2009-02-21
Nitratotris(triphenyl-phosphine)copper(I) methanol solvate.
2009-02-13
Bis(triphenyl-phosphine-κP)(tropolonato-κO,O')silver(I) dichloro-methane solvate.
2009-01-28
(3,5,7-Tribromo-tropolonato-κO,O')tris-(triphenyl-phosphine-κP)silver(I).
2009-01-14
Dicarbon-yl[2-hydr-oxy-3,5,7-tris-(mor-pho-linomethyl)cyclo-hepta-2,4,6-trien-onato(1-)-κO,O]rhodium(I).
2008-11-20
Pharmacological characterization of membrane-expressed human trace amine-associated receptor 1 (TAAR1) by a bioluminescence resonance energy transfer cAMP biosensor.
2008-09
The Collaborative Lithium Trials (CoLT): specific aims, methods, and implementation.
2008-08-12
Growing pains: contemporary knowledge and recommended practice.
2008-07-28
Effects of l-amphetamine sulfate on cognitive function in multiple sclerosis patients.
2008-06
Persistent downregulation of hippocampal CREB mRNA parallels a Y-maze deficit in adolescent rats following semi-chronic amphetamine administration.
2008-05
Ultrasonic vocalizations induced by sex and amphetamine in M2, M4, M5 muscarinic and D2 dopamine receptor knockout mice.
2008-04-02
Treatment of adults with attention-deficit/hyperactivity disorder.
2008-04
Treatment of adults with attention-deficit/hyperactivity disorder.
2008-02
l-Amphetamine improves poor sustained attention while d-amphetamine reduces overactivity and impulsiveness as well as improves sustained attention in an animal model of Attention-Deficit/Hyperactivity Disorder (ADHD).
2008-01-23
Comparison of the effects of deramciclane, ritanserin and buspirone on extracellular dopamine and its metabolites in striatum and nucleus accumbens of freely moving rats.
2008-01
The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia.
2007-10
Development and validation of a liquid chromatography/tandem mass spectrometry assay for the simultaneous determination of D-amphetamine and diphenhydramine in beagle dog plasma and its application to a pharmacokinetic study.
2007-07-01
Differential effects of the D- and L- isomers of amphetamine on pharmacological MRI BOLD contrast in the rat.
2007-07
A triazolam/amphetamine dose-effect interaction study: dissociation of effects on memory versus arousal.
2007-06
Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine.
2007-04
N-Methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) and N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) produce non-identical discriminative stimuli in rats.
2007-03
Analysis of pharmaceuticals in wastewater and removal using a membrane bioreactor.
2007-02
Effects of amphetamine isomers, methylphenidate and atomoxetine on synaptosomal and synaptic vesicle accumulation and release of dopamine and noradrenaline in vitro in the rat brain.
2007-02
Atomoxetine: a novel treatment for child and adult ADHD.
2006-12
The 5-HT3 receptor partial agonist MD-354 (meta-chlorophenylguanidine) enhances the discriminative stimulus actions of (+)amphetamine in rats.
2006-11-06
Chiral separation and quantification of R/S-amphetamine, R/S-methamphetamine, R/S-MDA, R/S-MDMA, and R/S-MDEA in whole blood by GC-EI-MS.
2006-10-02
alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats.
2006-10
Misuse of "study drugs:" prevalence, consequences, and implications for policy.
2006-06-09
Modulation of a (+)amphetamine discriminative stimulus in rats by 8-hydroxy-2-(N,N-di-n-propylamino)tetralin (8-OH DPAT).
2006-04
Relationship between temperature, dopaminergic neurotoxicity, and plasma drug concentrations in methamphetamine-treated squirrel monkeys.
2006-03
Efficacy of atomoxetine in adult attention-deficit/hyperactivity disorder: a drug-placebo response curve analysis.
2005-10-03
Patents

Patents

Sample Use Guides

In children from 3 to 5 years of age, start with 2.5 mg daily; daily dosage may be raised in increments of 2.5 mg at weekly intervals until optimal response is obtained. In children 6 years of age and older, start with 5 mg once or twice daily; daily dosage may be raised in increments of 5 mg at weekly intervals until optimal response is obtained. Only in rare cases will it be necessary to exceed a total of 40 mg per day. Give first dose on awakening; additional doses (1 or 2) at intervals of 4 to 6 hours.
Route of Administration: Oral
TAAR1 receptor activation was assayed in CHO cells stably expressing Gα16 and the hTAAR1 receptor. Cells were plated in HAM’s F-12 medium with 10% fetal bovine serum, 400 µg/ml hygromycin, and 400 µg/ml geneticin at 30,000 cells/well in 96-well, black, clear-bottom plates and incubated at 37 °C 5% CO2 overnight. Activation of hTAAR1 via LEVAMFETAMINE was assessed the next day using the Calcium 3 Assay Kit (Molecular Devices). On the day of assay, the culture medium was removed and the cells washed once in 100 µl HBSS buffer containing 0.78 mg/ml probenicid, followed by the addition of 100 µl HBSS buffer plus probenicid and 100 µl of Calcium 3 dye (one-third the suggested concentration). The cells were incubated with the dye at 37 °C for 1 h. LEVAMFETAMINE were evaluated using 10 different concentrations run in duplicate.
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:11:32 GMT 2025
Edited
by admin
on Wed Apr 02 08:11:32 GMT 2025
Record UNII
R87US8P740
Record Status Validated (UNII)
Record Version
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Name Type Language
AMPHETAMINE L-FORM
MI  
Preferred Name English
LEVAMFETAMINE
INN  
INN  
Official Name English
levamfetamine [INN]
Common Name English
AMPHETAMINE L-FORM [MI]
Common Name English
(-)-(R)-.ALPHA.-METHYLBENZENEETHANAMINE
Systematic Name English
AMFETAMINE, (R)-
Common Name English
LEVAMPHETAMINE
Common Name English
(-)-(R)-.ALPHA.-METHYLPHENETHYLAMINE
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 310.502
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
Code System Code Type Description
DRUG CENTRAL
1562
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
EVMPD
SUB08453MIG
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
WIKIPEDIA
Levoamphetamine
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
CHEBI
42724
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
SMS_ID
100000082801
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
ChEMBL
CHEMBL19393
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
INN
1313
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
NCI_THESAURUS
C170114
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
MERCK INDEX
m1849
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY Merck Index
PUBCHEM
32893
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
FDA UNII
R87US8P740
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
CAS
156-34-3
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-850-8
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID20166016
Created by admin on Wed Apr 02 08:11:32 GMT 2025 , Edited by admin on Wed Apr 02 08:11:32 GMT 2025
PRIMARY
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ACTIVE MOIETY