Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H13N |
Molecular Weight | 135.2062 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(N)CC1=CC=CC=C1
InChI
InChIKey=KWTSXDURSIMDCE-UHFFFAOYSA-N
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
Molecular Formula | C9H13N |
Molecular Weight | 135.2062 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.caremark.com/portal/asset/FEP_Rationale_Amphetamine.pdf
https://www.ncbi.nlm.nih.gov/pubmed/23539642
http://www.cesar.umd.edu/cesar/drugs/amphetamines.asp
Curator's Comment: description was created based on several sources, including
https://www.caremark.com/portal/asset/FEP_Rationale_Amphetamine.pdf
https://www.ncbi.nlm.nih.gov/pubmed/23539642
http://www.cesar.umd.edu/cesar/drugs/amphetamines.asp
Amphetamine is a potent central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers: levoamphetamine and dextroamphetamine. The mode of therapeutic action in ADHD is not known. Amphetamines are thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron and increase the release of these monoamines into the extraneuronal space. At higher dosages, they cause release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems. Amphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect. The drug interacts with VMAT enzymes to enhance release of DA and 5-HT from vesicles. It may also directly cause the reversal of DAT and SERT. Several currently prescribed amphetamine formulations contain both enantiomers, including Adderall, Dyanavel XR, and Evekeo, the last of which is racemic amphetamine sulfate. Amphetamine is also prescribed in enantiopure and prodrug form as dextroamphetamine and lisdexamfetamine respectively. Lisdexamfetamine is structurally different from amphetamine, and is inactive until it metabolizes into dextroamphetamine.
CNS Activity
Sources: https://nootropicscity.com/comprehensive-write-amphetamines-adderall-ritalin-vyvanse-concerta/
Curator's Comment: Amphetamines readily cross the blood-brain barrier to reach their primary sites of action in the brain. The acute administration of amphetamine produces a wide range of dose-dependent behavioral changes, including increased arousal or wakefulness, anorexia, hyperactivity, perseverative movements, and, in particular, a state of pleasurable affect, elation, and euphoria, which can lead to the abuse of the drug.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7751968 |
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Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=15602501 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DYANAVEL XR Approved UseINDICATIONS Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) and Narcolepsy. Attention Deficit Hyperactivity Disorder (ADHD) A diagnosis of Attention Deficit Hyperactivity Disorder (ADHD; DSM-IV®) implies the presence of hyperactive-impulsive or inattentive symptoms that caused impairment and were present before age 7 years. The symptoms must cause clinically significant impairment, e.g., in social, academic, or occupational functioning, and be present in two or more settings, e.g., school (or work) and at home. The symptoms must not be better accounted for by another mental disorder. For the Inattentive Type, at least six of the following symptoms must have persisted for at least 6 months: lack of attention to details/careless mistakes; lack of sustained attention; poor listener; failure to follow through on tasks; poor organization; avoids tasks requiring sustained mental effort; loses things; easily distracted; forgetful. For the Hyperactive-Impulsive Type, at least six of the following symptoms must have persisted for at least 6 months: fidgeting/squirming; leaving seat; inappropriate running/climbing; difficulty with quiet activities; “on the go;” excessive talking; blurting answers; can't wait turn; intrusive. The Combined Type requires both inattentive and hyperactive-impulsive criteria to be met. Special Diagnostic Considerations: Specific etiology of this syndrome is unknown, and there is no single diagnostic test. Adequate diagnosis requires the use not only of medical but of special psychological, educational, and social resources. Learning may or may not be impaired. The diagnosis must be based upon a complete history and evaluation of the child and not solely on the presence of the required number of DSM-IV® characteristics. Need for Comprehensive Treatment Program: Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets is indicated as an integral part of a total treatment program for ADHD that may include other measures (psychological, educational, social) for patients with this syndrome. Drug treatment may not be indicated for all children with this syndrome. Stimulants are not intended for use in the child who exhibits symptoms secondary to environmental factors and/or other primary psychiatric disorders, including psychosis. Appropriate educational placement is essential and psychosocial intervention is often helpful. When remedial measures alone are insufficient, the decision to prescribe stimulant medication will depend upon the physician's assessment of the chronicity and severity of the child's symptoms. Long-Term Use: The effectiveness of Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets for long-term use has not been systematically evaluated in controlled trials. Therefore, the physician who elects to use Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets for extended periods should periodically re-evaluate the long-term usefulness of the drug for the individual patient. Launch Date1.44521285E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
120 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1727 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
Title | Date | PubMed |
---|---|---|
[Amphetamine-induced psychosis]. | 1998 |
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Event-related potential indices of auditory selective attention in dependent amphetamine users. | 1999 Jun 1 |
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Inhibition of amphetamine- and apomorphine-induced behavioural effects by neuropeptide Y Y(1) receptor antagonist BIBO 3304. | 2000 Apr 27 |
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A comparison of the patterns of striatal Fos-like immunoreactivity induced by various dopamine agonists in rats. | 2000 Aug 4 |
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Lack of effect of repeated treatment with a glycineB receptor partial agonist on the amphetamine-induced hyperactivity in rats. | 2000 May-Jun |
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Amphetamine-induced toxicity in dopamine terminals in CD-1 and C57BL/6J mice: complex roles for oxygen-based species and temperature regulation. | 2001 |
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Present and future pharmacotherapeutic options for adult attention deficit/hyperactivity disorder. | 2001 Apr |
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SB-243213; a selective 5-HT2C receptor inverse agonist with improved anxiolytic profile: lack of tolerance and withdrawal anxiety. | 2001 Aug |
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Adderall for obsessive-compulsive disorder. | 2001 May |
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Double-blind, placebo-controlled study of single-dose amphetamine formulations in ADHD. | 2001 Nov |
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Differentially altered mGluR1 and mGluR5 mRNA expression in rat caudate nucleus and nucleus accumbens in the development and expression of behavioral sensitization to repeated amphetamine administration. | 2001 Sep 1 |
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Effects of amphetamine on the plus-maze discriminative avoidance task in mice. | 2002 Feb |
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24-hour ambulatory blood pressure monitoring in male children receiving stimulant therapy. | 2002 Jul-Aug |
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Cocaine and amphetamine attenuate the discriminative stimulus effects of naltrexone in opioid-dependent rhesus monkeys. | 2002 Jun |
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CaMKII regulates amphetamine-induced ERK1/2 phosphorylation in striatal neurons. | 2002 Jun 12 |
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The ability of amphetamine to evoke arc (Arg 3.1) mRNA expression in the caudate, nucleus accumbens and neocortex is modulated by environmental context. | 2002 Mar 15 |
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Case series: Adderall augmentation of serotonin reuptake inhibitors in childhood-onset obsessive compulsive disorder. | 2002 Summer |
Sample Use Guides
DYANAVEL XR (R (amphetamine) extended-release oral suspension) should be orally administered once daily in the morning with or without food. The dose should be individualized according to the needs and responses of the patient. Before administering the dose, shake the bottle of DYANAVEL XR.
In children 6 years of age and older, start with 2.5 mg or 5 mg once daily in the morning. The dose may be increase
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24672014
Curator's Comment: Amph increases the effects induced by βPEA on the LGC-55, indicating that Amph potentiates the effects generated by the biogenic amine βPEA
β-Phenylethylamine (βPEA) activates the amine-gated chloride channel LGC-55 more efficiently than amphetamine (Amph) (Km = 9 and 152 μm, respectively)
Substance Class |
Chemical
Created
by
admin
on
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Wed Jul 05 22:35:25 UTC 2023
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on
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Record UNII |
CK833KGX7E
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 250.101
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LIVERTOX |
50
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NDF-RT |
N0000175729
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WHO-VATC |
QN06BA01
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NCI_THESAURUS |
C47795
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DEA NO. |
1100
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WHO-ATC |
N06BA01
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CFR |
21 CFR 862.3100
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FDA ORPHAN DRUG |
405313
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DEA NO. |
7401
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NDF-RT |
N0000175739
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CFR |
21 CFR 310.502
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C62006
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27159
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195
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300-62-9
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DTXSID4022600
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D000661
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2679
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3287
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AMPHETAMINE
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M1849
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DB00182
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4804
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3007
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Amphetamine
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377
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CK833KGX7E
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SUB05418MIG
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206-096-2
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CK833KGX7E
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PA 003
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100000087217
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CHEMBL405
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725
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE |
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PRECURSOR->PARENT |
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METABOLIC ENZYME -> INHIBITOR |
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PRECURSOR->PARENT |
Immediate precursor
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PRECURSOR->PARENT |
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SALT/SOLVATE -> PARENT |
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PRECURSOR->PARENT |
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT |
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REAGENT->PARENT |
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SALT/SOLVATE -> PARENT |
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PRECURSOR->PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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PRECURSOR->PARENT |
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REAGENT->PARENT |
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PRECURSOR->PARENT |
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PRECURSOR->PARENT |
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
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DERIVATIVE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
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TARGET -> AGONIST |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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PARENT -> METABOLITE |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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PARENT -> METABOLITE ACTIVE |
MAJOR
URINE
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
UNSPECIFIED
EP
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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