Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13N.C6H10O4 |
Molecular Weight | 281.348 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]([H])(Cc1ccccc1)N.C(CCC(=O)O)CC(=O)O
InChI
InChIKey=OFCJKOOVFDGTLY-QRPNPIFTSA-N
InChI=1S/C9H13N.C6H10O4/c1-8(10)7-9-5-3-2-4-6-9;7-5(8)3-1-2-4-6(9)10/h2-6,8H,7,10H2,1H3;1-4H2,(H,7,8)(H,9,10)/t8-;/m0./s1
Molecular Formula | C6H10O4 |
Molecular Weight | 146.1414 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C9H13N |
Molecular Weight | 135.2066 |
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 |
|||
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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
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 |
---|---|---|
Agonist and antagonist activity of low efficacy D2 dopamine receptor agonists in rats discriminating d-amphetamine from saline. | 1992 Dec |
|
Effect of amphetamine on the expression of the metabotropic glutamate receptor 5 mRNA in developing rat brain. | 2000 Dec |
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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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No functional effects of embryonic neuronal grafts on motor deficits in a 3-nitropropionic acid rat model of advanced striatonigral degeneration (multiple system atrophy). | 2001 |
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Anorectic drugs and pulmonary hypertension from the bedside to the bench. | 2001 Apr |
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Resolution of stroke deficits following contralateral grafts of conditionally immortal neuroepithelial stem cells. | 2001 Apr |
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Determination of amphetamine in dog plasma by gas chromatography with mass selective detection. | 2001 Apr |
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A nitric oxide-dopamine link pathway in organum vasculosum laminae terminalis of rat brain exerts control over blood pressure. | 2001 Apr |
|
Effect of 6-hydroxydopamine or repeated amphetamine treatment on mesencephalic mRNA levels for AMPA glutamate receptor subunits in the rat. | 2001 Apr 20 |
|
Nicotine sensitization increases dendritic length and spine density in the nucleus accumbens and cingulate cortex. | 2001 Apr 27 |
|
Interleukin-2 potentiates novelty- and GBR 12909-induced exploratory activity. | 2001 Apr 27 |
|
Neural mechanisms of motion sickness. | 2001 Feb |
|
Tyrosine improves behavioral and neurochemical deficits caused by cold exposure. | 2001 Feb |
|
Differences in locomotor response to an inescapable novel environment predict sensitivity to aversive effects of amphetamine. | 2001 Feb |
|
Effects of acute D-amphetamine and ketamine on the performance of rats in a serial negative patterning procedure. | 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 |
|
Chronic inositol increases striatal D(2) receptors but does not modify dexamphetamine-induced motor behavior. Relevance to obsessive-compulsive disorder. | 2001 Feb |
|
Transcranial magnetic stimulation in an amphetamine hyperactivity model of mania. | 2001 Feb |
|
Comparison of the effects of infant handling, isolation, and nonhandling on acoustic startle, prepulse inhibition, locomotion, and HPA activity in the adult rat. | 2001 Feb |
|
Conditioned activity to amphetamine in transgenic mice expressing an antisense RNA against the glucocorticoid receptor. | 2001 Feb |
|
Drugs used in the treatment of attention-deficit/hyperactivity disorder affect postsynaptic firing rate and oscillation without preferential dopamine autoreceptor action. | 2001 Feb 15 |
|
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry. | 2001 Feb 25 |
|
Striatal dopamine sensitization to D-amphetamine in periadolescent but not in adult rats. | 2001 Jan |
|
Schedule-dependent effects of haloperidol and amphetamine: multiple-schedule task shows within-subject effects. | 2001 Jan |
|
Acute hydrocortisone administration does not affect subjective responses to d-amphetamine in humans. | 2001 Jan |
|
Distinct contributions of glutamate and dopamine receptors to temporal aspects of rodent working memory using a clinically relevant task. | 2001 Jan |
|
Modification of d-amphetamine-induced responses by baclofen in rats. | 2001 Jan |
|
[Analysis of the striato-pallidal interactions in regulation of avoidance behavior]. | 2001 Jan |
|
Neonatal dexamethasone on day 7 in rats causes behavioral alterations reflective of hippocampal, but not cerebellar, deficits. | 2001 Jan-Feb |
|
Developmental exposure to methylmercury alters behavioral sensitivity to D-amphetamine and pentobarbital in adult rats. | 2001 Jan-Feb |
|
The weaver mutant mouse: a model to study the ontogeny of dopamine transmission systems and their role in drug addiction. | 2001 Jun |
|
Entopeduncular lesions facilitate and thalamic lesions depress spontaneous and drug-evoked motor behavior in the hemiparkinsonian rat. | 2001 Jun 1 |
|
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis. | 2001 Mar |
|
Effects of d-amphetamine on the performance of rats in an animal analogue of the A-X continuous performance test. | 2001 Mar |
|
Differential sensitivity to NaCl for inhibitors and substrates that recognize mutually exclusive binding sites on the neuronal transporter of dopamine in rat striatal membranes. | 2001 Mar |
|
Adrenergic hyperactivity and metanephrine excess in the nucleus accumbens after prefrontocortical dopamine depletion. | 2001 Mar |
|
Acute myocardial infarction associated with amphetamine use. | 2001 Mar |
|
Amphetamine selectively blocks inhibitory glutamate transmission in dopamine neurons. | 2001 Mar |
|
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 |
|
Dissociations between the effects of intra-accumbens administration of amphetamine and exposure to a novel environment on accumbens dopamine and cortical acetylcholine release. | 2001 Mar 16 |
|
Serotonin transporter localization in the hamster suprachiasmatic nucleus. | 2001 Mar 2 |
|
Amphetamine-stimulated cortical acetylcholine release: role of the basal forebrain. | 2001 Mar 9 |
|
Glial cell line-derived neurotrophic factor (GDNF) gene delivery protects dopaminergic terminals from degeneration. | 2001 May |
|
Amphetamine normalizes the electrical activity of dopamine neurons in the ventral tegmental area following prenatal ethanol exposure. | 2001 May |
|
Chronic amphetamine exposure during the preweanling period does not affect avoidance learning or novelty-seeking of adult rats. | 2001 May |
|
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 |
|
Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene. | 2001 May 1 |
|
Genes in drug abuse. | 2001 May 1 |
|
Post-training injections of catecholaminergic drugs do not modulate fear conditioning in rats and mice. | 2001 May 4 |
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
by
admin
on
Edited
Sat Jun 26 06:47:56 UTC 2021
by
admin
on
Sat Jun 26 06:47:56 UTC 2021
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Record UNII |
YYI1A8W4TQ
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Record Status |
Validated (UNII)
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Record Version |
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-
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49800024
Created by
admin on Sat Jun 26 06:47:56 UTC 2021 , Edited by admin on Sat Jun 26 06:47:56 UTC 2021
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64770-52-1
Created by
admin on Sat Jun 26 06:47:56 UTC 2021 , Edited by admin on Sat Jun 26 06:47:56 UTC 2021
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YYI1A8W4TQ
Created by
admin on Sat Jun 26 06:47:56 UTC 2021 , Edited by admin on Sat Jun 26 06:47:56 UTC 2021
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CHEMBL612
Created by
admin on Sat Jun 26 06:47:56 UTC 2021 , Edited by admin on Sat Jun 26 06:47:56 UTC 2021
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64770-52-1
Created by
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DBSALT001324
Created by
admin on Sat Jun 26 06:47:56 UTC 2021 , Edited by admin on Sat Jun 26 06:47:56 UTC 2021
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