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Benzedrine

Amphetamine
INN: Amfetamine
An image of the amphetamine compound
A 3d image of the D-amphetamine compound
Clinical data
Pronunciation Listeni/æmˈfɛtəmn/
Trade names Adderall, Dyanavel XR, Evekeo, others
AHFS/Drugs.com amphetamine
License data
Pregnancy
category
  • US: C (Risk not ruled out)
Dependence
liability
Physical: none
Psychological: moderate
Addiction
liability
Moderate
Routes of
administration
Medical: oral, intravenous
Recreational: oral, insufflation, rectal, intravenous, intramuscular
Drug class CNS stimulant
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability Oral 75–100%
Protein binding 15–40%
Metabolism CYP2D6,DBH,FMO3
Metabolites 4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, benzoic acid, hippuric acid, norephedrine, phenylacetone
Onset of action IR dosing: 30–60 minutes
XR dosing: 1.5–2 hours
Biological half-life D-amph: 9–11 hours
L-amph: 11–14 hours
pH-dependent: 8–31 hours
Duration of action IR dosing: 3–7 hours
XR dosing: 12 hours
Excretion Primarily renal;
pH-dependent range: 1–75%
Identifiers
Synonyms α-methylphenethylamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
ECHA InfoCard 100.005.543
Chemical and physical data
Formula C9H13N
Molar mass 135.20622 g/mol
3D model (Jmol)
Chirality Racemic mixture
Density .913 g/cm3 at 25 °C
Melting point 11.3 °C (52.3 °F) (predicted)
Boiling point 203 °C (397 °F) at 760 mmHg
  

Amphetamine (contracted from alphamethylphenethylamine) is a potent central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers:levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers, levoamphetamine and dextroamphetamine, in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.

The first pharmaceutical amphetamine was Benzedrine, a brand which was used to treat a variety of conditions. Currently, pharmaceutical amphetamine is prescribed as racemic amphetamine, Adderall,dextroamphetamine, or the inactive prodrug lisdexamfetamine. Amphetamine, through activation of a trace amine receptor, increases monoamine and excitatory neurotransmitter activity in the brain, with its most pronounced effects targeting the catecholamine neurotransmitters norepinephrine and dopamine.


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