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Dexamfetamine
Dexamfetamine
Synonyms Generic names:
Dexamphetamine (AAN),
dextroamphetamine (USAN).
Street names: dex, dexies, dexy, oranges, panama or peaches.
Brand names Dexedrine, Dextrostat, ProCentra, Zenzedi
IUPAC name

IUPAC name
(2S)-1-phenylpropan-2-amine
ChemSpider

5621

DrugBank

DB01576

PubChem

5826

PDB fields

N/A

Formula

C9H13N

InChI
InChI
1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
InChIKey
InChIKey
KWTSXDURSIMDCE-QMMMGPOBSA-N
SMILES
SMILES
C[C@H](N)CC1=CC=CC=C1
(Jmol 3D structure)
Mol. mass

135.2062 g/mol

Dexamfetamine (INN and BAN) is a stimulant of the amfetamine class,[note 1] that is both a popular drug of abuse and a medically-utilized drug that is used to treat attention-deficit/hyperactivity disorder and narcolepsy.[1]

Medical usesEdit

Medically it is primarily used to treat narcolepsy and ADHD, although lesser-utilized (and no longer recommended due to safer and more effective modern alternatives exist) uses include: obesity, depression, fatigue in Parkinson's disease and multiple sclerosis, etc.[1] It is a treatment for metamfetamine addiction that seems to be slightly more effective than the other treatments; it is basically used as a replacement therapy, sort of like methadone for heroin addicts.[2]

Side effectsEdit

In the short-termEdit

Note: Preliminary information on side effect frequency may be found here. These side effects are when given in the usual therapeutic doses.

Common side effects include: digestive changes/complaints such as nausea, stomach cramps, diarrhoea, dry mouth, loss of appetite and weight loss; psychiatric/neurological changes including anxiety, irritability, insomnia, aggression, headache, euphoria, nightmares, dizziness and cardiovascular changes including high heart rate, heart palpitations and changes in blood pressure.[1][3] Other side effects that are likely frequent (but data on its exact frequency is unavailable) include sexual side effects like impotence and libido changes.[1]

Less common, yet serious side effects include: vascular complications or heart-related complications, including heart attacks and strokes and sudden heart arrest (leading to unexplained death); kidney-related complications like rhabdomyolysis and kidney failure; brain-related complications, including mania, psychosis and seizures.[1]

In the long-termEdit

These side effects are mostly rare ones and can include growth stunting (in children) and cardiomyopathy.[1]

Mechanism of actionEdit

It, like other amfetamines, works via activating TAAR1, which inhibits the reuptake of the monoamine neurotransmitters, while simultaneously inhibiting VMAT2, leading to the release of the monoamines from the storage vesicles.[4][5]

PropertiesEdit

Its physical appearance, as its sulfate salt, is a white or almost white, odourless or almost odourless and crystalline powder.[1]

The elimination half-life of oral dexamfetamine is 7-24 hours, depending on urinary pH.[1] It is chiefly excreted in the urine. It usually comes medically as the sulfate salt.[1]

See alsoEdit

External linksEdit

NotesEdit

  1. More specifically it is the dextrorotatory (d-, or S-) enantiomer of the amfetamine molecule

Reference listEdit

  1. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 Brayfield, A, ed. (12 December 2013). "Dexamfetamine Sulfate". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 5 June 2014.
  2. Pérez-Mañá, C; Castells, X; Vidal, X; Casas, M; Capellà, D (March 2011). "Efficacy of indirect dopamine agonists for psychostimulant dependence: a systematic review and meta-analysis of randomized controlled trials.". Journal of Substance Abuse Treatment 40 (2): 109–22. PMID 21036508. doi:10.1016/j.jsat.2010.08.012. 
  3. Rossi, S, ed. (July 2014). "Dexamphetamine". Australian Medicines Handbook. Adelaide, Australia: Australian Medicines Handbook Pty Ltd. Retrieved 12 September 2014. 
  4. Zucchi, R; Chiellini, G; Scanlan, TS; Grandy, DK (December 2006). "Trace amine-associated receptors and their ligands.". British Journal of Pharmacology 149 (8): 967–78. doi:10.1038/sj.bjp.0706948. PMC 2014643. PMID 17088868.
  5. Sotnikova, TD; Caron, MG; Gainetdinov, RR; Grandy, DK (August 2009). "Trace amine-associated receptors as emerging therapeutic targets.". Molecular pharmacology 76 (2): 229–35. doi:10.1124/mol.109.055970. PMC 2713119. PMID 19389919.

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