Amphetamine

Amphetamine
INN: Amfetamine
Clinical data
Pronunciation	/æmˈfɛtəmiːn/ ⓘ
Trade names	Evekeo, Adderall, others
Other names	α-methylphenethylamine
AHFS/Drugs.com	Monograph
MedlinePlus	a616004
License data	US DailyMed: Amphetamine;
Dependence; liability	Physical: Low Psychological: Moderate
Addiction; liability	High
Routes of; administration	Medical: oral, intravenous; Recreational: oral, insufflation, rectal, intravenous, intramuscular
Drug class	CNS stimulant, anorectic
ATC code	N06BA01 (WHO) N06BA02 (WHO) N06BA12 (WHO);
Physiological data
Receptors	TAAR1, VMAT2, 5HT1A
Metabolism	CYP2D6, DBH, FMO3
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A3 (Psychoactive drugs); CA: Schedule I; DE: Anlage III (Special prescription form required); NZ: Class B; UK: Class B; US: WARNINGSchedule II; UN: Psychotropic Schedule II;
Pharmacokinetic data
Bioavailability	Oral: 75–100%
Protein binding	20%
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
Elimination half-life	D-amph: 9–11 hours; L-amph: 11–14 hours; pH-dependent: 7–34 hours
Duration of action	IR dosing: 3–6 hours; XR dosing: 8–12 hours
Excretion	Primarily renal;; pH-dependent range: 1–75%
Identifiers
	IUPAC name (RS)-1-phenylpropan-2-amine;
CAS Number	300-62-9 ;
PubChem CID	3007;
IUPHAR/BPS	4804;
DrugBank	DB00182 ;
ChemSpider	13852819 ;
UNII	CK833KGX7E;
KEGG	D07445 ;
ChEBI	CHEBI:2679 ;
ChEMBL	ChEMBL405 ;
NIAID ChemDB	018564;
CompTox Dashboard (EPA)	DTXSID4022600 ;
ECHA InfoCard	100.005.543
Chemical and physical data
Formula	C9H13N
Molar mass	135.210 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Density	.936 g/cm3 at 25 °C
Melting point	146 °C (295 °F)
Boiling point	203 °C (397 °F) at 760 mmHg
	SMILES NC(C)Cc1ccccc1;
	InChI InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 ; Key:KWTSXDURSIMDCE-UHFFFAOYSA-N ;
	(verify)

Amphetamine (contracted from alpha-methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It 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 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 amphetamine pharmaceutical 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 increases monoamine and excitatory neurotransmission in the brain, with its most pronounced effects targeting the norepinephrine and dopamine neurotransmitter systems.

At therapeutic doses, amphetamine causes emotional and cognitive effects such as euphoria, change in desire for sex, increased wakefulness, and improved cognitive control. It induces physical effects such as improved reaction time, fatigue resistance, and increased muscle strength. Larger doses of amphetamine may impair cognitive function and induce rapid muscle breakdown. Addiction is a serious risk with heavy recreational amphetamine use, but is unlikely to occur from long-term medical use at therapeutic doses. Very high doses can result in psychosis (e.g., delusions and paranoia) which rarely occurs at therapeutic doses even during long-term use. Recreational doses are generally much larger than prescribed therapeutic doses and carry a far greater risk of serious side effects.

Amphetamine belongs to the phenethylamine class. It is also the parent compound of its own structural class, the substituted amphetamines, which includes prominent substances such as bupropion, cathinone, MDMA, and methamphetamine. As a member of the phenethylamine class, amphetamine is also chemically related to the naturally occurring trace amine neuromodulators, specifically phenethylamine and N-methylphenethylamine, both of which are produced within the human body. Phenethylamine is the parent compound of amphetamine, while N-methylphenethylamine is a positional isomer of amphetamine that differs only in the placement of the methyl group.

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