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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N.C4H6O4
Molecular Weight 253.2943
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVAMFETAMINE SUCCINATE

SMILES

OC(=O)CCC(O)=O.C[C@@H](N)CC1=CC=CC=C1

InChI

InChIKey=HVANWDSTOFDWRV-DDWIOCJRSA-N
InChI=1S/C9H13N.C4H6O4/c1-8(10)7-9-5-3-2-4-6-9;5-3(6)1-2-4(7)8/h2-6,8H,7,10H2,1H3;1-2H2,(H,5,6)(H,7,8)/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

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
82%
LEVAMFETAMINE plasma
Homo sapiens
PubMed

PubMed

TitleDatePubMed
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.
2001 Dec
Acute doses of d-amphetamine and bupropion increase cigarette smoking.
2001 Sep
Amphetamine salt compound treatment for adults with attention deficit hyperactivity disorder.
2002 Apr
Central stimulants as discriminative stimuli. Asymmetric generalization between (-)ephedrine and S(+)methamphetamine.
2002 Dec
Effect of repeated treatment with high doses of selegiline on behaviour, striatal dopaminergic transmission and tyrosine hydroxylase mRNA levels.
2002 Jan
The stimulus effect of 5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline is similar to that of cocaine but different from that of amphetamine.
2002 Jan-Feb
Effect of amphetamine and phencyclidine on DNA-binding activities of serum response and dyad symmetry elements.
2003 Apr
PF 9601N [N-(2-propynyl)-2-(5-benzyloxy-indolyl) methylamine], a new MAO-B inhibitor, attenuates MPTP-induced depletion of striatal dopamine levels in C57/BL6 mice.
2003 Feb
Modulation of the stimulus effects of (+)amphetamine by the 5-HT6 antagonist MS-245.
2004 Jun
Modulation of a (+)amphetamine discriminative stimulus in rats by 8-hydroxy-2-(N,N-di-n-propylamino)tetralin (8-OH DPAT).
2006 Apr
Relationship between temperature, dopaminergic neurotoxicity, and plasma drug concentrations in methamphetamine-treated squirrel monkeys.
2006 Mar
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 Oct 2
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 Feb
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 Mar
The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia.
2007 Oct
The Collaborative Lithium Trials (CoLT): specific aims, methods, and implementation.
2008 Aug 12
Growing pains: contemporary knowledge and recommended practice.
2008 Jul 28
Effects of l-amphetamine sulfate on cognitive function in multiple sclerosis patients.
2008 Jun
National outbreak of Acanthamoeba keratitis associated with use of a contact lens solution, United States.
2009 Aug
Profiling of levoamphetamine and related substances in dexamphetamine sulfate by capillary electrophoresis.
2009 Dec 5
Nitratotris(triphenyl-phosphine)copper(I) methanol solvate.
2009 Feb 13
(3,5,7-Tribromo-tropolonato-κO,O')tris-(triphenyl-phosphine-κP)silver(I).
2009 Jan 14
Bis(triphenyl-phosphine-κP)(tropolonato-κO,O')silver(I) dichloro-methane solvate.
2009 Jan 28
Bis[tris-(4-fluoro-phen-yl)phosphine-κP](tropolonato-κO,O')copper(I).
2009 Mar 28
Prenatal inflammation-induced hypoferremia alters dopamine function in the adult offspring in rat: relevance for schizophrenia.
2010 Jun 4
CE assay for simultaneous determination of charged and neutral impurities in dexamphetamine sulfate using a dual CD system.
2010 May
New and extended-action treatments in the management of ADHD: a critical appraisal of lisdexamfetamine in adults and children.
2010 May 25
Bis[2-(methyl-amino)-troponato]copper(II).
2010 Nov 6
Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.
2011 Dec 1
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 Fri Dec 15 15:11:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:11:24 GMT 2023
Record UNII
STC9O9MD79
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVAMFETAMINE SUCCINATE
USAN  
USAN  
Official Name English
(-)-(R)-.ALPHA.-METHYLPHENETHYLAMINE SUCCINATE (1:1)
Systematic Name English
LEVAMPHETAMINE SUCCINATE
Common Name English
BUTANEDIOIC ACID, COMPD. WITH (-)-(R)-.ALPHA.-METHYLBENZENEETHANAMINE (1:1)
Common Name English
LEVAMFETAMINE SUCCINATE [USAN]
Common Name English
Code System Code Type Description
FDA UNII
STC9O9MD79
Created by admin on Fri Dec 15 15:11:24 GMT 2023 , Edited by admin on Fri Dec 15 15:11:24 GMT 2023
PRIMARY
CAS
5634-40-2
Created by admin on Fri Dec 15 15:11:24 GMT 2023 , Edited by admin on Fri Dec 15 15:11:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID50971771
Created by admin on Fri Dec 15 15:11:24 GMT 2023 , Edited by admin on Fri Dec 15 15:11:24 GMT 2023
PRIMARY
NCI_THESAURUS
C170115
Created by admin on Fri Dec 15 15:11:24 GMT 2023 , Edited by admin on Fri Dec 15 15:11:24 GMT 2023
PRIMARY
PUBCHEM
68638
Created by admin on Fri Dec 15 15:11:24 GMT 2023 , Edited by admin on Fri Dec 15 15:11:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL19393
Created by admin on Fri Dec 15 15:11:24 GMT 2023 , Edited by admin on Fri Dec 15 15:11:24 GMT 2023
PRIMARY
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