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
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
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 |
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 Date-1.4688E10 |
|||
Primary | PAREDRINE Approved UseADDERALL® is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) and
Narcolepsy. Launch Date-1.4688E10 |
|||
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 |
---|---|---|
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 |
|
Discriminative stimulus properties of alpha-ethyltryptamine optical isomers. | 2001 Oct-Nov |
|
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 |
|
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 |
|
Non-linearity in combined effects of ELF magnetic field and amphetamine on motor activity in rats. | 2004 Apr 2 |
|
Modulation of the stimulus effects of (+)amphetamine by the 5-HT6 antagonist MS-245. | 2004 Jun |
|
Safety, efficacy and extended duration of action of mixed amphetamine salts extended-release capsules for the treatment of ADHD. | 2005 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 |
|
Atomoxetine: a novel treatment for child and adult ADHD. | 2006 Dec |
|
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 |
|
The 5-HT3 receptor partial agonist MD-354 (meta-chlorophenylguanidine) enhances the discriminative stimulus actions of (+)amphetamine in rats. | 2007 Jun-Jul |
|
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 |
|
The Collaborative Lithium Trials (CoLT): specific aims, methods, and implementation. | 2008 Aug 12 |
|
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 |
|
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 |
|
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 |
|
CE assay for simultaneous determination of charged and neutral impurities in dexamphetamine sulfate using a dual CD system. | 2010 May |
|
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 |
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
Wed Jul 05 22:42:56 UTC 2023
by
admin
on
Wed Jul 05 22:42:56 UTC 2023
|
Record UNII |
STC9O9MD79
|
Record Status |
Validated (UNII)
|
Record Version |
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-
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Official Name | English | ||
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STC9O9MD79
Created by
admin on Wed Jul 05 22:42:56 UTC 2023 , Edited by admin on Wed Jul 05 22:42:56 UTC 2023
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5634-40-2
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admin on Wed Jul 05 22:42:56 UTC 2023 , Edited by admin on Wed Jul 05 22:42:56 UTC 2023
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DTXSID50971771
Created by
admin on Wed Jul 05 22:42:56 UTC 2023 , Edited by admin on Wed Jul 05 22:42:56 UTC 2023
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C170115
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68638
Created by
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CHEMBL19393
Created by
admin on Wed Jul 05 22:42:56 UTC 2023 , Edited by admin on Wed Jul 05 22:42:56 UTC 2023
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |