Substance

ID:1364

Dextroamphetamine

Names and Identifiers
Brand Name
DephadrenDexacapsDexedrine SpansuleDexidrineSympaminDextrostatDesoxynDexedrineAmsustainDexadrine
Synonyms
S(+)-amphetamineDexamfetaminum [inn-latin]Dexamfetamina [inn-spanish]DesamfetaminaD-amphetamine(s)-(+)-beta-phenylisopropylamine(+)-alpha-methylphenylethylamine(+)-alpha-methylphenethylamineDextroamphetamine1-Methyl-2-phenylethylamine(s)-alpha-methylphenethylamine(S)-1-Phenyl-2-propanamineDextroamphetamineDextroamphetamine sulfate(+)-(s)-amphetamine(S)-1-phenyl-2-aminopropane(2S)-1-phenylpropan-2-amineDexamphetamineD-(s)-amphetamine(S)-1-phenyl-2-propylamine(s)-(+)-amphetamine(2S)-(+)-Amphetamine(+)-phenaminum(+)-amphetamineDexamfetamineD-alpha-methylphenethylamineD-2-Amino-1-phenylpropaneD-1-Phenyl-2-aminopropanDexanfetamina [inn-spanish]Dexamphetaminum [inn-latin]D-amD-1-Phenyl-2-aminopropane(s)-amphetamine(s)-alpha-phenylethylamined-1-Phenyl-2-aminopropan [German]D-(+)-amphetamine(s)-alpha-methylbenzeneethanamine
IUPAC Traditional name
dextroamphetamine
IUPAC name
(2S)-1-phenylpropan-2-amine
Registration numbers
PubChem CID
CAS Number
PubChem SID
Properties
Physical Property
Hydrophobicity(logP)
1.76 [SANGSTER (1994); similar isomer]
Molecule Details
Drug Groups
illicit; approved
Description
Dextroamphetamine is the dextrorotary stereoisomer of the amphetamine molecule, which can take two different forms. It is a slightly polar, weak base and is lipophilic.
Indication
Used to treat attention deficit hyperactivity disorder (ADHD).
Pharmacology
Amphetamines such as dextroamphetamine are noncatecholamine, sympathomimetic amines with CNS stimulant activity. Peripheral actions include elevations of systolic and diastolic blood pressures and weak bronchodilator and respiratory stimulant action. There is neither specific evidence that clearly establishes the mechanism whereby amphetamines produce mental and behavioral effects in children, nor conclusive evidence regarding how these effects relate to the condition of the central nervous system.
Toxicity
In rats, the oral LD50 of dextroamphetamine sulfate is 96.8 mg/kg. Manifestations of acute overdosage with amphetamines include restlessness, tremor, hyperreflexia, rhabdomyolysis, rapid respiration, hyperpyrexia, confusion, assaultiveness, hallucinations, panic states. Fatigue and depression usually follow the central stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension, and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Fatal poisoning is usually preceded by convulsions and coma.
Affected Organisms
Humans and other mammals
Biotransformation
Hepatic.
Absorption
Oral bioavailability is over 75%.
Half Life
10-28 hours (average is approximately 12 hours)
References
• Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H: Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems. Xenobiotica. 1984 Nov;14(11):861-6. [Pubmed]
• Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. [Pubmed]
• Wagner GJ, Rabkin R: Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry. 2000 Jun;61(6):436-40. [Pubmed]
• Martinsson L, Yang X, Beck O, Wahlgren NG, Eksborg S: Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol. 2003 Sep-Oct;26(5):270-6. [Pubmed]
• Butefisch CM, Davis BC, Sawaki L, Waldvogel D, Classen J, Kopylev L, Cohen LG: Modulation of use-dependent plasticity by d-amphetamine. Ann Neurol. 2002 Jan;51(1):59-68. [Pubmed]
External Links
Molecular Spectra
No Data Available
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References
• Wagner GJ, Rabkin R: Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry. 2000 Jun;61(6):436-40. Pubmed
• Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H: Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems. Xenobiotica. 1984 Nov;14(11):861-6. Pubmed
• Martinsson L, Yang X, Beck O, Wahlgren NG, Eksborg S: Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol. 2003 Sep-Oct;26(5):270-6. Pubmed
• Butefisch CM, Davis BC, Sawaki L, Waldvogel D, Classen J, Kopylev L, Cohen LG: Modulation of use-dependent plasticity by d-amphetamine. Ann Neurol. 2002 Jan;51(1):59-68. Pubmed
• Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. Pubmed