Amphetamine

Amphetamine
INN: Amfetamine

Clinical data
Pronunciation	i/æmˈfɛtəmiːn/
Trade names	Adderall, Dyanavel XR, Evekeo, others
AHFS/Drugs.com	amphetamine
License data	US FDA: Amphetamine
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	N06BA01 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Prescription only) NZ: Class B UK: Class B US: Schedule II UN: Psychotropic Schedule II
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
IUPAC name (RS)-1-phenylpropan-2-amine
Synonyms	α-methylphenethylamine
CAS Number	300-62-9 Y
PubChem CID	3007
IUPHAR/BPS	4804
DrugBank	DB00182 Y
ChemSpider	13852819 Y
UNII	CK833KGX7E
KEGG	D07445 Y
ChEBI	CHEBI:2679 Y
ChEMBL	CHEMBL405 Y
NIAID ChemDB	018564
PDB ligand	FRD (PDBe, RCSB PDB)
ECHA InfoCard	100.005.543
Chemical and physical data
Formula	C9H13N
Molar mass	135.20622 g/mol
3D model (Jmol)	Interactive image
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
SMILES NC(CC1=CC=CC=C1)C
InChI InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 Y Key:KWTSXDURSIMDCE-UHFFFAOYSA-N Y

Amphetamine (contracted from alpha‑methylphenethylamine) 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.