Structure via PubChem · Public domain (PubChem)
dextroamphetamine
Sign in to saveAlso known as Dexedrine, Dextrostat, (+)-alpha-Methylphenylethylamine, (S)-(+)-beta-Phenylisopropylamine, (S)-1-Phenyl-2-propylamine, dexamphetamine, (AlphaS)-alpha-methylbenzeneethanamine, (+)-(S)-amphetamine
Dextroamphetamine is a central nervous system (CNS) stimulant and enantiomer of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used illicitly to enhance cognitive and athletic performance, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.
Key facts
- Drug.chirality
- Dextrorotatory enantiomer
- Drug.SMILES
- C[C@@H](Cc1ccccc1)N
- Drug.StdInChI
- 1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
- Drug.StdInChIKey
- KWTSXDURSIMDCE-QMMMGPOBSA-N
- Drug.density
- 0.913
- Drug.boiling_point
- 201.5
- Drug.solubility
- 20
- Drug.sol_units
- mg per ml
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 596899008
- Drug.INN
- Dexamfetamine
- Drug.image
- Dextroamphetamine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.imageL
- D-Amphetamine-3D-balls.png
- Drug.image_classL
- bg-transparent
- Drug.widthL
- 125px
via Wikipedia infobox
Chemical data
- Formula
- C9H13N
- Molecular weight
- 135.21 g/mol
- IUPAC name
- (2S)-1-phenylpropan-2-amine
- SMILES
- C[C@@H](CC1=CC=CC=C1)N
- InChIKey
- KWTSXDURSIMDCE-QMMMGPOBSA-N
- XLogP
- 1.8
- Polar surface area
- 26 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
7,600 papers- Modafinil Versus Amphetamine-Dextroamphetamine For Idiopathic Hypersomnia and Narcolepsy Type 2: A Randomized, Blinded, Non-inferiority Trial.CNS drugs · 2024
- Dextroamphetamine-morphine analgesia.The New England journal of medicine · 1977
- Transdermal dextroamphetamine (Xelstrym) for ADHD.The Medical letter on drugs and therapeutics · 2023
- Amphetamine, Dextroamphetamine Mixed Salts-Associated Ischemic Colitis.American journal of therapeutics · 2022
- Dextroamphetamine-sulfate-induced dyskinesias.JAMA · 1968
via PubMed
Wikidata facts
- Subclass of
- DL-amphetamine
- Has part
- hydrogen
- Mass
- 135.104799
- Has use
- medication
Show 13 more facts
- found in taxon
- Vachellia rigidula
- chemical formula
- C₉H₁₃N
- significant drug interaction
- tranylcypromine
- World Health Organisation international non-proprietary name
- dexamfetamine
- medical condition treated
- attention deficit hyperactivity disorder
- canonical SMILES
- CC(CC1=CC=CC=C1)N
- isomeric SMILES
- C[C@@H](CC1=CC=CC=C1)N
- defined daily dose
- 15
- subject has role
- nootropic
- Commons category
- Dextroamphetamine
- physically interacts with
- Solute carrier family 18 member A2
- stereoisomer of
- (R)-amphetamine
- legal status (medicine)
- boxed warning
Sources (9)
via Wikidata · CC0
~17 min read
Encyclopedic overview
26 sectionsContents
- Uses
- Medical
- ADHD
- Narcolepsy
- Enhancing performance
- Recreational
- Contraindications
- Adverse effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Related endogenous compounds
- Pharmacokinetics
- History, society, and culture
- Formulations
- Transdermal dextroamphetamine patches
- Dextroamphetamine sulfate
- Lisdexamfetamine
- Adderall
- Research
- Schizophrenia
- Notes
- Reference notes
- References
- External links
Dextroamphetamine is a central nervous system (CNS) stimulant and enantiomer of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used illicitly to enhance cognitive and athletic performance, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.
The amphetamine molecule exists as two enantiomers, levoamphetamine and dextroamphetamine. Dextroamphetamine is the dextrorotatory, or 'right-handed', enantiomer and exhibits more pronounced effects on the central nervous system than levoamphetamine. Pharmaceutical dextroamphetamine sulfate is available as both a brand name and generic drug in a variety of dosage forms. Dextroamphetamine is sometimes prescribed as the inactive prodrug lisdexamfetamine.
Excerpted from Wikipedia’s “dextroamphetamine” article, available under the CC BY-SA 4.0 licence.