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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
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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.3 µM [EC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Efficacy of atomoxetine in adult attention-deficit/hyperactivity disorder: a drug-placebo response curve analysis.
2005 Oct 3
Modulation of a (+)amphetamine discriminative stimulus in rats by 8-hydroxy-2-(N,N-di-n-propylamino)tetralin (8-OH DPAT).
2006 Apr
Atomoxetine: a novel treatment for child and adult ADHD.
2006 Dec
Misuse of "study drugs:" prevalence, consequences, and implications for policy.
2006 Jun 9
Relationship between temperature, dopaminergic neurotoxicity, and plasma drug concentrations in methamphetamine-treated squirrel monkeys.
2006 Mar
alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats.
2006 Oct
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
Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine.
2007 Apr
Analysis of pharmaceuticals in wastewater and removal using a membrane bioreactor.
2007 Feb
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
Differential effects of the D- and L- isomers of amphetamine on pharmacological MRI BOLD contrast in the rat.
2007 Jul
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 Jul 1
A triazolam/amphetamine dose-effect interaction study: dissociation of effects on memory versus arousal.
2007 Jun
The 5-HT3 receptor partial agonist MD-354 (meta-chlorophenylguanidine) enhances the discriminative stimulus actions of (+)amphetamine in rats.
2007 Jun-Jul
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
Treatment of adults with attention-deficit/hyperactivity disorder.
2008 Apr
Ultrasonic vocalizations induced by sex and amphetamine in M2, M4, M5 muscarinic and D2 dopamine receptor knockout mice.
2008 Apr 2
The Collaborative Lithium Trials (CoLT): specific aims, methods, and implementation.
2008 Aug 12
Treatment of adults with attention-deficit/hyperactivity disorder.
2008 Feb
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 Jan
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 Jan 23
Growing pains: contemporary knowledge and recommended practice.
2008 Jul 28
Effects of l-amphetamine sulfate on cognitive function in multiple sclerosis patients.
2008 Jun
Persistent downregulation of hippocampal CREB mRNA parallels a Y-maze deficit in adolescent rats following semi-chronic amphetamine administration.
2008 May
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 Nov 20
Pharmacological characterization of membrane-expressed human trace amine-associated receptor 1 (TAAR1) by a bioluminescence resonance energy transfer cAMP biosensor.
2008 Sep
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
2-Isobutyl-2-phosphabicyclo-[3.3.1]nonane 2-selenide.
2009 Feb 21
(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
The effects of L-amphetamine sulfate on cognition in MS patients: results of a randomized controlled trial.
2009 Jul
Assessing susceptibility to age-related macular degeneration with proteomic and genomic biomarkers.
2009 Jun
Cellular immune response to intrastriatally implanted allogeneic bone marrow stromal cells in a rat model of Parkinson's disease.
2009 Jun 5
Neonatal amphetamine exposure and hippocampus-mediated behaviors.
2009 Mar
Bis[tris-(4-fluoro-phen-yl)phosphine-κP](tropolonato-κO,O')copper(I).
2009 Mar 28
Peripheral vasculopathy associated with psychostimulant treatment in children with attention-deficit/hyperactivity disorder.
2010 Apr
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 Jun
Prenatal inflammation-induced hypoferremia alters dopamine function in the adult offspring in rat: relevance for schizophrenia.
2010 Jun 4
Amphetamine treatment during early postnatal development transiently restricts somatic growth.
2010 Mar 27
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
Reasons for illicit drug use in people with schizophrenia: Qualitative study.
2010 Nov 22
New approaches in the management of multiple sclerosis.
2010 Nov 24
Bis[2-(methyl-amino)-troponato]copper(II).
2010 Nov 6
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 Sep
Impurity profiling of dexamphetamine sulfate by cyclodextrin-modified microemulsion electrokinetic chromatography.
2010 Sep
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 Vivo Use Guide
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
In Vitro Use Guide
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 Tue Oct 22 19:51:01 UTC 2019
Edited
by admin
on Tue Oct 22 19:51:01 UTC 2019
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
CAS
5634-40-2
Created by admin on Tue Oct 22 19:51:01 UTC 2019 , Edited by admin on Tue Oct 22 19:51:01 UTC 2019
PRIMARY
PUBCHEM
68638
Created by admin on Tue Oct 22 19:51:01 UTC 2019 , Edited by admin on Tue Oct 22 19:51:01 UTC 2019
PRIMARY
ChEMBL
CHEMBL19393
Created by admin on Tue Oct 22 19:51:01 UTC 2019 , Edited by admin on Tue Oct 22 19:51:01 UTC 2019
PRIMARY
Related Record Type Details
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY