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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N
Molecular Weight 135.2066
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXTROAMPHETAMINE

SMILES

C[C@@]([H])(Cc1ccccc1)N

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

HIDE SMILES / InChI

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

Description
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.

Originator

Curator's Comment:: 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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DEXEDRINE

Approved Use

Narcolepsy. 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 Date

3.15532804E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
24.7 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
431 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
12.1 h
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Dopaminergic mRNA expression in the intact substantia nigra of unilaterally 6-OHDA-lesioned and grafted rats: an in situ hybridization study.
2001
Stimulation of metabotropic but not ionotropic glutamatergic receptors in the nucleus accumbens is required for the D-amphetamine-induced release of functional dopamine.
2001
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
Anorectic drugs and pulmonary hypertension from the bedside to the bench.
2001 Apr
Resolution of stroke deficits following contralateral grafts of conditionally immortal neuroepithelial stem cells.
2001 Apr
Determination of amphetamine in dog plasma by gas chromatography with mass selective detection.
2001 Apr
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
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
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
Role of mitochondrial dysfunction and dopamine-dependent oxidative stress in amphetamine-induced toxicity.
2001 Jan
What is a "low dose" of d-amphetamine for inducing behavioral effects in laboratory rats?
2001 Jan 1
Significance of glutamate and dopamine neurons in the ventral pallidum in the expression of behavioral sensitization to amphetamine.
2001 Jan 19
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
Computer-aided screening for hallucinogenic and stimulant amphetamines with gas chromatography-Fourier transform infrared spectroscopy (GC-FTIR).
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
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
Seizure activity and hyperthermia potentiate the increases in dopamine and serotonin extracellular levels in the amygdala during exposure to d-amphetamine.
2001 Mar
Previous exposure to amphetamine enhances the subsequent locomotor response to a D1 dopamine receptor agonist when glutamate reuptake is inhibited.
2001 Mar 1
Dopaminergic role in stimulant-induced wakefulness.
2001 Mar 1
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
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
Genes in drug abuse.
2001 May 1
Patents

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
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 Sat Jun 26 09:16:39 UTC 2021
Edited
by admin
on Sat Jun 26 09:16:39 UTC 2021
Record UNII
TZ47U051FI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXTROAMPHETAMINE
HSDB   MI   USAN   VANDF  
USAN  
Official Name English
AMPHETAMINE, D-
Common Name English
DEXAMFETAMINE [INN]
Common Name English
DEXAMFETAMINE
INN   WHO-DD  
INN  
Official Name English
DEXAMFETAMINE [WHO-DD]
Common Name English
AMFETAMINE, (S)-
Common Name English
DEXIDRINE
Common Name English
DEXTROAMPHETAMINE [USAN]
Common Name English
NSC-73713
Code English
DEXTROAMPHETAMINE [HSDB]
Common Name English
(S)-1-PHENYL-2-AMINOPROPANE
Systematic Name English
(+)-.ALPHA.-METHYLPHENETHYLAMINE
Systematic Name English
DEXAMPHETAMINE
Common Name English
(+)-(S)-AMPHETAMINE
Systematic Name English
BENZENEETHANAMINE, .ALPHA.-METHYL-, (S)-
Systematic Name English
DEXTROAMPHETAMINE [MI]
Common Name English
D-AMPHETAMINE
Common Name English
DEXTROAMPHETAMINE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QN06BA02
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
CFR 21 CFR 310.502
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
WHO-ATC N06BA02
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
NDF-RT N0000175739
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
NCI_THESAURUS C47795
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
EPA PESTICIDE CODE 600005
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
LIVERTOX 293
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
NDF-RT N0000175729
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
Code System Code Type Description
RXCUI
3288
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY RxNorm
EPA CompTox
51-64-9
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
CAS
51-64-9
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
INN
1430
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
DRUG CENTRAL
841
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL612
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
FDA UNII
TZ47U051FI
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
LACTMED
Dextroamphetamine
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
EVMPD
SUB07019MIG
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
DRUG BANK
DB01576
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
WIKIPEDIA
DEXTROAMPHETAMINE
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
PUBCHEM
5826
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-112-1
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
MERCK INDEX
M4226
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY Merck Index
IUPHAR
2147
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
MESH
D003913
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
NCI_THESAURUS
C28981
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
HSDB
3055
Created by admin on Sat Jun 26 09:16:40 UTC 2021 , Edited by admin on Sat Jun 26 09:16:40 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
METABOLITE -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC Adult
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION