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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
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
Monoamine oxidase-inhibition and MPTP-induced neurotoxicity in the non-human primate: comparison of rasagiline (TVP 1012) with selegiline.
2001
Four-choice drug discrimination in pigeons.
2001 Dec
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.
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
Discriminative stimulus properties of alpha-ethyltryptamine optical isomers.
2001 Oct-Nov
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
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 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
Further characterization of the stimulus properties of 5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline.
2002 May
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
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
Triazolam-amphetamine interaction: dissociation of effects on memory versus arousal.
2003 Mar
Free operant and discrete trial performance of mice in the nine-hole box apparatus: validation using amphetamine and scopolamine.
2004 Jul
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
alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats.
2006 Oct
Analysis of pharmaceuticals in wastewater and removal using a membrane bioreactor.
2007 Feb
Differential effects of the D- and L- isomers of amphetamine on pharmacological MRI BOLD contrast in the rat.
2007 Jul
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
Ultrasonic vocalizations induced by sex and amphetamine in M2, M4, M5 muscarinic and D2 dopamine receptor knockout mice.
2008 Apr 2
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
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
National outbreak of Acanthamoeba keratitis associated with use of a contact lens solution, United States.
2009 Aug
2-Isobutyl-2-phosphabicyclo-[3.3.1]nonane 2-selenide.
2009 Feb 21
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
Bis[tris-(4-fluoro-phen-yl)phosphine-κP](tropolonato-κO,O')copper(I).
2009 Mar 28
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
Bis[2-(methyl-amino)-troponato]copper(II).
2010 Nov 6
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:39:21 GMT 2023
Edited
by admin
on Sat Dec 16 16:39:21 GMT 2023
Record UNII
R87US8P740
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
AMPHETAMINE L-FORM
MI  
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.502
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1562
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
EVMPD
SUB08453MIG
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
WIKIPEDIA
Levoamphetamine
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
CHEBI
42724
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
SMS_ID
100000082801
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL19393
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
INN
1313
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
NCI_THESAURUS
C170114
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
MERCK INDEX
m1849
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY Merck Index
PUBCHEM
32893
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
FDA UNII
R87US8P740
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
CAS
156-34-3
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-850-8
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID20166016
Created by admin on Sat Dec 16 16:39:22 GMT 2023 , Edited by admin on Sat Dec 16 16:39:22 GMT 2023
PRIMARY
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