DL-amphetamine

Also known as β-aminopropylbenzene, β-phenylisopropylamine, 1-phenyl-2-aminopropane, α-methylbenzeneethaneamine, α-methylphenethylamine, (±)-amphetamine, 1-phenylpropan-2-amin, alpha-methylbenzeneethaneamine

Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy; it is also used to treat binge eating disorder in the form of lisdexamfetamine. 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

AI overview

DL-amphetamine is a stimulant medication that affects the central nervous system and is prescribed to treat conditions like ADHD and narcolepsy, though it has also been used historically for nasal congestion and depression. It matters medically because it can be an effective treatment for these disorders, but it is tightly controlled as a prescription drug in many countries due to potential for misuse and because it can be used recreationally or as a performance enhancer.

AI-generated from the Wikipedia summary — may contain errors.

Key facts

Drug.Watchedfields: correct
Drug.synonyms: α-methylphenethylamine, β-phenylisopropylamine, thyramine
Drug.ChEBI: 2679
Drug.ChEMBL: 405
Drug.NIAID_ChemDB: 018564
Drug.C: 9
Drug.H: 13
Drug.N: 1
Drug.chirality: Racemic mixture
Drug.density: .936
Drug.density_notes: at 25 °C
Drug.SMILES: NC(C)Cc1ccccc1
Drug.Verifiedfields: correct
Drug.verifiedrevid: 851154960r
Drug.INN: Amfetamine
Drug.image: Amphetamine structure.svg
Drug.image_class: skin-invert-image
Drug.width: 215px

via Wikipedia infobox

Chemical data

Formula: C9H13N
Molecular weight: 135.21 g/mol
IUPAC name: 1-phenylpropan-2-amine
SMILES: CC(CC1=CC=CC=C1)N
InChIKey: KWTSXDURSIMDCE-UHFFFAOYSA-N
XLogP: 1.8
Polar surface area: 26 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

via PubChem

Research

34,964 papers

Amphetamine.Lancet (London, England) · 1947HOWARD CDOI: 10.1016/s0140-6736(47)91924-7
Amphetamine-related disorders.ReviewThe Journal of the Louisiana State Medical Society : official organ of the Louisiana State Medical Society · 1998Czerwinski WP
Amphetamine drugs.Public health reports (Washington, D.C. : 1896) · 1960FLEMMING AS
[Amphetamine abuse and drug interactions].ReviewUgeskrift for laeger · 2014Horwitz H, Skanning P, Askaa B et al.
Amphetamine in surgery.Lancet (London, England) · 1947FATTI LDOI: 10.1016/s0140-6736(47)90166-9
A comparison of the behavioral effects of l- and dl-cathinone and d-amphetamine.The Journal of pharmacology and experimental therapeutics · 1981Johanson CE, Schuster CR
Overdose of amphetamine.Lancet (London, England) · 1949FRANKEL EDOI: 10.1016/s0140-6736(49)91903-0
Discriminative stimulus properties of a low dl-amphetamine dose.Archives internationales de pharmacodynamie et de therapie · 1976Colpaert FC, Kuyps JJ, Niemegeers CJ et al.

via PubMed

Wikidata facts

Mass: 135.104799

Show 8 more facts

Commons category: Amphetamine
World Health Organisation international non-proprietary name: 苯丙胺
chemical formula: C₉H₁₃N
canonical SMILES: CC(CC1=CC=CC=C1)N
melting point: 11.3
boiling point: 203
density: 0.936
defined daily dose: 15

Sources (11)

via Wikidata · CC0

~74 min read

Article

44 sections

Contents

Uses
Medical
ADHD
Binge eating disorder
Narcolepsy
Enhancing performance
Cognitive performance
Physical performance
Recreational
Contraindications
Adverse effects
Physical
Psychological
Reinforcement disorders
Addiction
Biomolecular mechanisms
Pharmacological treatments
Behavioral treatments
Dependence and withdrawal
Overdose
Toxicity
Psychosis
Drug interactions{{anchor|Interactions}}
Pharmacology
Pharmacodynamics
Dopamine
Norepinephrine
Serotonin
Other neurotransmitters, peptides, hormones, and enzymes
Sex-dependent differences
Pharmacokinetics
Pharmacomicrobiomics
Related endogenous compounds
Chemistry
Substituted derivatives
Synthesis
Detection in body fluids
History, society, and culture
Legal status
Pharmaceutical products
Notes
Reference notes
References
External links

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. The first amphetamine pharmaceutical was Benzedrine. Pharmaceutical amphetamine is prescribed as racemic amphetamine, Adderall, dextroamphetamine, or lisdexamfetamine. Amphetamine increases monoamine and excitatory neurotransmission in the brain, with its most pronounced effects targeting the norepinephrine and dopamine neurotransmitter systems.