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
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
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 |
---|---|---|
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
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.
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ACTIVE MOIETY
SUBSTANCE RECORD