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-QMMMGPOBSA-N
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://blackpoppymag.wordpress.com/substances/dexedrine-dexamphetamine/
Curator's Comment: description was created based on several sources, including
https://blackpoppymag.wordpress.com/substances/dexedrine-dexamphetamine/
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. Dextroamphetamine is useful for those with ADHD and Narcolepsy. It improves self-control for people who have a hard time naturally controlling themselves. Dextroamphetamine aids a person learning and memory of words, and perhaps makes the brain stronger. When a person given dextroamphetamine is tested, their brain is extremely active in the brain parts required for the test and radically less active in other parts. Short practice sessions with dextroamphetamine have a greater effect on learning than sessions without dextroamphetamine. Dextroamphetamine raises decision-making scores, improves choices, and changes beliefs about rewards; at the same time, dextroamphetamine barely—if at all—affects guesses of time. Those who feel lower amounts of joy from dextroamphetamine have greater impulsivity improvements compared to those who feel extreme happiness. The drug should be avoided for those who have hypersensitivity to amphetamines, a history of drug abuse, cardiovascular diseases, hypertensive disease, hyperthyroidism, or in those with glaucoma. In 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dextroamphetamine, and in 1937 Smith, Kline, and French introduced Dexedrine tablets, under the tradename Dexedrine. In the United States, Dexedrine tablets were approved to treat narcolepsy, attention disorders, depression, and obesity. Dexedrine, along with other sympathomimetic, was eventually classified as schedule II, the most restrictive category possible for a drug with recognized medical uses. The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). Modulation of serotonergic pathways may contribute to the calming effect.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17239355 |
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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/19244097 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DEXEDRINE Approved UseNarcolepsy. Attention Deficit Disorder with Hyperactivity. As an integral part of a total treatment program that typically includes other measures (psychological, educational, social) for patients (ages 6 years to 16 years) with this syndrome. A diagnosis of Attention Deficit Hyperactivity Disorder (ADHD; DSM-IV) implies the presence of the 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 2 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 6 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 6 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. Launch Date3.15532804E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
24.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXTROAMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
36.6 ng/mL |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXTROAMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
431 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXTROAMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXTROAMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
12 h |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXTROAMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 4.0 |
likely | likely (co-administration study) Comment: Amphetamines and amphetamine derivatives are known to be metabolized, to some degree, by cytochrome P450 2D6 (CYP2D6) and display minor inhibition of CYP2D6 metabolism; concomitant use of DEXEDRINE and CYP2D6 inhibitors may increase the exposure of DEXEDRINE; Page: 4.0 |
PubMed
Title | Date | PubMed |
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Lithium prevention of amphetamine-induced 'manic' excitement and of reserpine-induced 'depression' in mice: possible role of 2-phenylethylamine. | 1978 Dec 8 |
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Does guanfacine cause hallucinations in children? | 1999 |
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Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons. | 1999 Jun |
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Seizures caused by concomitant use of lindane and dextroamphetamine in a child with attention deficit hyperactivity disorder. | 2000 Aug |
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Effect of amphetamine on the expression of the metabotropic glutamate receptor 5 mRNA in developing rat brain. | 2000 Dec |
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Dexamphetamine substitution in the treatment of amphetamine abuse: an initial investigation. | 2000 Feb |
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Effect of the 5-HT3 receptor antagonist ondansetron on amphetamine-induced hyperactivity and stereotypy in rats. | 2000 Jul |
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Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. | 2000 Jun |
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Dopaminergic mRNA expression in the intact substantia nigra of unilaterally 6-OHDA-lesioned and grafted rats: an in situ hybridization study. | 2001 |
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Stimulation of metabotropic but not ionotropic glutamatergic receptors in the nucleus accumbens is required for the D-amphetamine-induced release of functional dopamine. | 2001 |
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Effects of systemic injections of dopaminergic agents on the habituation of rats submitted to an open field test. | 2001 |
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Periodic maternal separation of neonatal rats produces region- and gender-specific effects on biogenic amine content in postmortem adult brain. | 2001 Apr |
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Nicotine sensitization increases dendritic length and spine density in the nucleus accumbens and cingulate cortex. | 2001 Apr 27 |
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Tyrosine improves behavioral and neurochemical deficits caused by cold exposure. | 2001 Feb |
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The D3R partial agonist, BP 897, attenuates the discriminative stimulus effects of cocaine and D-amphetamine and is not self-administered. | 2001 Feb |
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Conditioned activity to amphetamine in transgenic mice expressing an antisense RNA against the glucocorticoid receptor. | 2001 Feb |
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Neurotensin gene expression and behavioral responses following administration of psychostimulants and antipsychotic drugs in dopamine D(3) receptor deficient mice. | 2001 Feb |
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Long term modulation of the HPA axis by the hippocampus. Behavioral, biochemical and immunological endpoints in rats exposed to chronic mild stress. | 2001 Feb |
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Selective inhibition of amine oxidases differently potentiate the hypophagic effect of benzylamine in mice. | 2001 Feb 9 |
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[Analysis of the striato-pallidal interactions in regulation of avoidance behavior]. | 2001 Jan |
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Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. | 2001 Jan |
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Synthesis of 4-methyl-5-arylpyrimidines and 4-arylpyrimidines: route specific markers for the Leuckardt preparation of amphetamine, 4-methoxyamphetamine, and 4-methylthioamphetamine. | 2001 Jan 1 |
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Significance of glutamate and dopamine neurons in the ventral pallidum in the expression of behavioral sensitization to amphetamine. | 2001 Jan 19 |
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Differential sensitivities to the lethal, but not the neurotoxic, effects of p-chloroamphetamine in inbred rat strains. | 2001 Jan 5 |
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Neonatal dexamethasone on day 7 in rats causes behavioral alterations reflective of hippocampal, but not cerebellar, deficits. | 2001 Jan-Feb |
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Developmental exposure to methylmercury alters behavioral sensitivity to D-amphetamine and pentobarbital in adult rats. | 2001 Jan-Feb |
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Entopeduncular lesions facilitate and thalamic lesions depress spontaneous and drug-evoked motor behavior in the hemiparkinsonian rat. | 2001 Jun 1 |
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Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis. | 2001 Mar |
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Adrenergic hyperactivity and metanephrine excess in the nucleus accumbens after prefrontocortical dopamine depletion. | 2001 Mar |
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Amphetamine selectively blocks inhibitory glutamate transmission in dopamine neurons. | 2001 Mar |
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Lobeline inhibits the neurochemical and behavioral effects of amphetamine. | 2001 Mar |
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Locomotor effects of acute and repeated threshold doses of amphetamine and methylphenidate: relative roles of dopamine and norepinephrine. | 2001 Mar |
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Previous exposure to amphetamine enhances the subsequent locomotor response to a D1 dopamine receptor agonist when glutamate reuptake is inhibited. | 2001 Mar 1 |
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Differential effects of endomorphin-1 and -2 on amphetamine sensitization: neurochemical and behavioral aspects. | 2001 Mar 1 |
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Sexual behavior induction of c-Fos in the nucleus accumbens and amphetamine-stimulated locomotor activity are sensitized by previous sexual experience in female Syrian hamsters. | 2001 Mar 15 |
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Determination of residues in the norepinephrine transporter that are critical for tricyclic antidepressant affinity. | 2001 Mar 16 |
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Glial cell line-derived neurotrophic factor (GDNF) gene delivery protects dopaminergic terminals from degeneration. | 2001 May |
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The variable number of tandem repeats polymorphism of the dopamine transporter gene is not associated with significant change in dopamine transporter phenotype in humans. | 2001 May |
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Changes in dopamine efflux associated with extinction, CS-induced and d-amphetamine-induced reinstatement of drug-seeking behavior by rats. | 2001 May |
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Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene. | 2001 May 1 |
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Genes in drug abuse. | 2001 May 1 |
Sample Use Guides
Usual dose is 5 to 60 mg per day in divided doses, depending on the individual patient response. Narcolepsy seldom occurs in children under 12 years of age; however, when it does, DEXEDRINE may be used. The suggested initial dose for patients aged 6 to 12 is 5 mg daily; daily dose may be raised in increments of 5 mg at weekly intervals until an optimal response is obtained. In patients 12 years of age and older, start with 10 mg daily; daily dosage may be raised in increments of 10 mg at weekly intervals until an optimal response is obtained. If bothersome adverse reactions appear (e.g., insomnia or anorexia), dosage should be reduced. SPANSULE capsules may be used for once-a-day dosage wherever appropriate.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6428136
Curator's Comment: The action of several concentrations of d-amphetamine on the NADH-tetrazolium reductase histochemical reaction has been studied in several nervous regions of rats. The facts observed have demonstrated that d-amphetamine increases the intensity of the histochemical reaction by its action on NADH-oxido-reductase activity in all nervous regions studied.
Unknown
Substance Class |
Chemical
Created
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admin
on
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Fri Dec 16 16:29:00 UTC 2022
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on
Fri Dec 16 16:29:00 UTC 2022
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Record UNII |
TZ47U051FI
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN06BA02
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CFR |
21 CFR 310.502
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WHO-ATC |
N06BA02
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NDF-RT |
N0000175739
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NCI_THESAURUS |
C47795
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EPA PESTICIDE CODE |
600005
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LIVERTOX |
293
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NDF-RT |
N0000175729
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3288
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DTXSID8022907
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TZ47U051FI
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51-64-9
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73713
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4469
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1430
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841
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CHEMBL612
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TZ47U051FI
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Dextroamphetamine
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SUB07019MIG
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DB01576
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DEXTROAMPHETAMINE
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5826
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200-112-1
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M4226
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2147
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D003913
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C28981
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3055
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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METABOLITE -> PARENT | |||
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Adult PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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