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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N.ClH
Molecular Weight 171.667
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVAMFETAMINE HYDROCHLORIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

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
Four-choice drug discrimination in pigeons.
2001 Dec
A force-plate actometer for quantitating rodent behaviors: illustrative data on locomotion, rotation, spatial patterning, stereotypies, and tremor.
2001 May 30
Hydrogen peroxide production in mouse tissues after acute d-amphetamine administration. Influence of monoamine oxidase inhibition.
2001 Oct
Dopamine receptor blockade in the rat medial prefrontal cortex reduces spontaneous and amphetamine-induced activity and does not affect prepulse inhibition.
2002 Dec
Central stimulants as discriminative stimuli. Asymmetric generalization between (-)ephedrine and S(+)methamphetamine.
2002 Dec
Effect of PMA optical isomers and 4-MTA in PMMA-trained rats.
2002 May
Intravenous self-administration of amphetamine is increased in a rat model of depression.
2002 Oct
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
Amphetamine enhances Ca2+ entry and catecholamine release via nicotinic receptor activation in bovine adrenal chromaffin cells.
2003 Jan 26
The effect of amphetamine on Kamin blocking and overshadowing.
2003 Jul
Behavioral sensitization to amphetamine in rats: changes in the rhythm of head movements during focused stereotypies.
2003 Nov
Amphetamine salt compound treatment for adults with attention deficit hyperactivity disorder.
2004 Feb
Modulation of the stimulus effects of (+)amphetamine by the 5-HT6 antagonist MS-245.
2004 Jun
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
Impaired response to amphetamine and neuronal degeneration in the nucleus accumbens of autoimmune MRL-lpr mice.
2006 Jan 6
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
Differential effects of the D- and L- isomers of amphetamine on pharmacological MRI BOLD contrast in the rat.
2007 Jul
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 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
Growing pains: contemporary knowledge and recommended practice.
2008 Jul 28
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
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
The effects of L-amphetamine sulfate on cognition in MS patients: results of a randomized controlled trial.
2009 Jul
Neonatal amphetamine exposure and hippocampus-mediated behaviors.
2009 Mar
Peripheral vasculopathy associated with psychostimulant treatment in children with attention-deficit/hyperactivity disorder.
2010 Apr
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
Reasons for illicit drug use in people with schizophrenia: Qualitative study.
2010 Nov 22
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 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.
Name Type Language
LEVAMFETAMINE HYDROCHLORIDE
Common Name English
BENZENEETHANAMINE, .ALPHA.-METHYL-, HYDROCHLORIDE, (.ALPHA.R)-
Common Name English
LEVAMPHETAMINE HYDROCHLORIDE
Common Name English
LEVAMFETAMINE HCL
Common Name English
BENZENEETHANAMINE, .ALPHA.-METHYL-, HYDROCHLORIDE (1:1), (.ALPHA.R)-
Common Name English
NSC-126789
Code English
BENZENEETHANAMINE, .ALPHA.-METHYL-, HYDROCHLORIDE, (R)-
Systematic Name English
Code System Code Type Description
FDA UNII
164AR976VT
Created by admin on Fri Dec 15 15:23:56 GMT 2023 , Edited by admin on Fri Dec 15 15:23:56 GMT 2023
PRIMARY
PUBCHEM
12215104
Created by admin on Fri Dec 15 15:23:56 GMT 2023 , Edited by admin on Fri Dec 15 15:23:56 GMT 2023
PRIMARY
NSC
126789
Created by admin on Fri Dec 15 15:23:56 GMT 2023 , Edited by admin on Fri Dec 15 15:23:56 GMT 2023
PRIMARY
CAS
41820-21-7
Created by admin on Fri Dec 15 15:23:56 GMT 2023 , Edited by admin on Fri Dec 15 15:23:56 GMT 2023
PRIMARY