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Dextroamphetamine

Catalog No. DB01576 Name DrugBank
CAS Number 51-64-9 Website http://www.ualberta.ca/
M. F. C9H13N Telephone (780) 492-3111
M. W. 135.20622 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 67

SYNONYMS

IUPAC name
(2S)-1-phenylpropan-2-amine
IUPAC Traditional name
dextroamphetamine
Brand Name
Dexedrine Spansule
Sympamin
Dextrostat
Dexacaps
Desoxyn
Dexedrine
Amsustain
Dephadren
Dexadrine
Dexidrine
Synonyms
D-1-Phenyl-2-aminopropane
Dexanfetamina [inn-spanish]
D-2-Amino-1-phenylpropane
1-Methyl-2-phenylethylamine
Dextroamphetamine
D-amphetamine
d-1-Phenyl-2-aminopropan [German]
D-(s)-amphetamine
D-(+)-amphetamine
(s)-alpha-methylbenzeneethanamine
(2S)-(+)-Amphetamine
(+)-alpha-methylphenylethylamine
Dexamphetaminum [inn-latin]
Dexamfetamine
Desamfetamina
D-am
D-alpha-methylphenethylamine
D-1-Phenyl-2-aminopropan
(s)-amphetamine
(s)-alpha-methylphenethylamine
(S)-1-phenyl-2-propylamine
(S)-1-Phenyl-2-propanamine
(S)-1-phenyl-2-aminopropane
(s)-(+)-beta-phenylisopropylamine
(s)-(+)-amphetamine
(+)-phenaminum
(+)-amphetamine
(+)-alpha-methylphenethylamine
Dextroamphetamine sulfate
S(+)-amphetamine
Dexamfetaminum [inn-latin]
Dexamfetamina [inn-spanish]
(s)-alpha-phenylethylamine
(2S)-1-phenylpropan-2-amine
(+)-(s)-amphetamine
Dexamphetamine

DATABASE IDS

CAS Number 51-64-9
PubChem CID 5826
PubChem SID 46506252

PROPERTIES

Hydrophobicity(logP) 1.76 [SANGSTER (1994); similar isomer]

DETAILS

Description (English)
Item Information
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
Wikipedia
RxList
Drugs.com

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
  • 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
  • Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. Pubmed