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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
Structure of DEXTROAMPHETAMINE

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

HIDE SMILES / InChI

Molecular Formula C9H13N
Molecular Weight 135.2062
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VYVANSE
Primary
VYVANSE
Primary
DEXEDRINE

Cmax

ValueDoseCo-administeredAnalytePopulation
47.9 ng/mL
70 mg 1 times / day multiple, oral
LISDEXAMFETAMINE plasma
Homo sapiens
24.7 ng/mL
10 mg single, oral
DEXTROAMPHETAMINE plasma
Homo sapiens
36.6 ng/mL
15 mg single, oral
DEXTROAMPHETAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
60.7 ng × h/mL
70 mg 1 times / day multiple, oral
LISDEXAMFETAMINE plasma
Homo sapiens
431 ng × h/mL
10 mg single, oral
DEXTROAMPHETAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
12 h
70 mg 1 times / day multiple, oral
LISDEXAMFETAMINE plasma
Homo sapiens
12.1 h
10 mg single, oral
DEXTROAMPHETAMINE plasma
Homo sapiens
12 h
15 mg single, oral
DEXTROAMPHETAMINE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Attention-deficit/hyperactivity disorder: Initial: 30 mg once daily in the morning; may increase in increments of 10 mg or 20 mg at weekly intervals until optimal response is obtained; maximum: 70 mg/day. Binge eating disorder: Initial: 30 mg once daily in the morning; may titrate in increments of 20 mg at weekly intervals to target dose of 50 to 70 mg once daily (maximum: 70 mg/day).
Route of Administration: Oral
In Vitro Use Guide
Incubation of lisdexamfetamine in microsomal suspensions at concentrations ranging from 0.01 to 100 M showed no concentration-dependent inhibition for any of the isoenzymes under investigation (CYP1A2, CYP2A6, CYP2B6, CYP2C9, CYP2C19, CYP2D6, CYP3A, CYP3A4).
Substance Class Chemical
Record UNII
TZ47U051FI
Record Status Validated (UNII)
Record Version