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
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
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 |
DescriptionSources: https://www.drugbank.ca/drugs/DB09571Curator'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
Sources: https://www.drugbank.ca/drugs/DB09571
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22037049 |
1.3 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PAREDRINE Approved UseADDERALL® is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) and
Narcolepsy. Launch Date1969 |
|||
Primary | PAREDRINE Approved UseADDERALL® is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) and
Narcolepsy. Launch Date1969 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29174216/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29174216/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
357.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29174216/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29174216/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29174216/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29174216/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
82% |
LEVAMFETAMINE plasma | Homo sapiens |
PubMed
Title | Date | PubMed |
---|---|---|
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
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22037049
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
Edited
Sat Dec 16 16:39:21 GMT 2023
by
admin
on
Sat Dec 16 16:39:21 GMT 2023
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Record UNII |
R87US8P740
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Record Status |
Validated (UNII)
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Record Version |
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-
Download
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CFR |
21 CFR 310.502
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1562
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SUB08453MIG
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Levoamphetamine
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42724
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100000082801
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CHEMBL19393
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1313
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C170114
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m1849
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32893
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R87US8P740
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156-34-3
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205-850-8
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DTXSID20166016
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