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 | C9H13N |
Molecular Weight | 135.2062 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
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 | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|---|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
82% |
LEVAMFETAMINE plasma | Homo sapiens |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Effect of amphetamine and phencyclidine on DNA-binding activities of serum response and dyad symmetry elements. | 2003 Apr |
|
The effect of amphetamine on Kamin blocking and overshadowing. | 2003 Jul |
|
Triazolam-amphetamine interaction: dissociation of effects on memory versus arousal. | 2003 Mar |
|
Age-related differences in MK-801- and amphetamine-induced locomotor and stereotypic activities of rats. | 2003 Sep |
|
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 |
|
Safety, efficacy and extended duration of action of mixed amphetamine salts extended-release capsules for the treatment of ADHD. | 2005 Jun |
|
Misuse of "study drugs:" prevalence, consequences, and implications for policy. | 2006 Jun 9 |
|
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 |
|
Analysis of pharmaceuticals in wastewater and removal using a membrane bioreactor. | 2007 Feb |
|
The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. | 2007 Oct |
|
Effects of l-amphetamine sulfate on cognitive function in multiple sclerosis patients. | 2008 Jun |
|
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 |
|
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 |
|
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 |
|
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
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
Mon Mar 31 17:49:31 GMT 2025
by
admin
on
Mon Mar 31 17:49:31 GMT 2025
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Record UNII |
STC9O9MD79
|
Record Status |
Validated (UNII)
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Record Version |
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-
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STC9O9MD79
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5634-40-2
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DTXSID50971771
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300000055199
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C170115
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68638
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CHEMBL19393
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ACTIVE MOIETY |