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DL-amphetamine

File:Amphetamine_structure.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ179452· pop 69· linked from 4,261 articles

DL-amphetamine

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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

OverviewAI-generated

DL-amphetamine is a chemical compound with the formula C₉H₁₃N. Its IUPAC name is 1-phenylpropan-2-amine. The substance has a molecular mass of 135.104799 and a density of 0.936. It melts at 11.3 degrees and boils at 203 degrees. The defined daily dose is 15.

Chemical properties include a charge of 0, one hydrogen bond donor, and one hydrogen bond acceptor. The xlogp value is 1.8, and the topological polar surface area is 26. The canonical SMILES notation for the molecule is CC(CC1=CC=CC=C1)N.

Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still 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 Ų
H-bond donors
1
H-bond acceptors
1
Formal charge
0

via PubChem

Research

34,964 papers

via PubMed

Wikidata facts

Mass
135.104799
Has use
medication
Show 16 more facts
significant drug interaction
tranylcypromine
Commons category
Amphetamine
topic's main category
Category:Amphetamine
World Health Organisation international non-proprietary name
苯丙胺
physically interacts with
solute carrier family 6 member 3
chemical formula
C₉H₁₃N
medical condition treated
obesity
canonical SMILES
CC(CC1=CC=CC=C1)N
melting point
11.3
boiling point
203
density
0.936
subject has role
nootropic
different from
D-methamphetamine
found in taxon
Senegalia berlandieri
defined daily dose
15
legal status (medicine)
boxed warning
Sources (11)

via Wikidata · CC0

~74 min read

Encyclopedic overview

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 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 health risks associated with recreational use.

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.

Excerpted from Wikipedia’s “DL-amphetamine” article, available under the CC BY-SA 4.0 licence.

Gallery (13)

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via Wikidata sitelinks · CC0