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D-methamphetamine

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

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D-methamphetamine

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Also known as N-methylamphetamine pito-1342, (S)-N,α-dimethylbenzeneethanamine, pure, d-1-phenyl-2-methylaminopropane, base, ice, chalk, S-methamphetamine

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OverviewAI-generated

D-methamphetamine, also referred to as dextromethamphetamine, is a chemical compound with the formula C₁₀H₁₅N. Its IUPAC name is (2S)-N-methyl-1-phenylpropan-2-amine. The substance has a mass of 149.12 and a defined daily dose of 15.

Chemical properties include an xlogp of 2.1 and a topological polar surface area of 12. The molecule contains one hydrogen bond donor and one hydrogen bond acceptor, with a charge of 0. It is associated with 180 PubMed entries and is referenced by 4,349 other encyclopedia articles.

Synthesized by Vinony from 21 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.verifiedrevid
589084691
Drug.INN
Metamfetamine
Drug.image
Methamphetamine structure.svg
Drug.image_class
skin-invert
Drug.width
200px
Drug.caption
Skeletal formula of methamphetamine
Drug.imageL
D-Methamphetamine MV.png
Drug.image_classL
bg-transparent
Drug.widthL
125px
Drug.imageR
L-Methamphetamine MV.png
Drug.image_classR
bg-transparent
Drug.widthR
125px
Drug.captionLR
Ball-and-stick models of methamphetamine enantiomers
Drug.chirality
Racemic mixture
Drug.pronounce
(), (), ()
Drug.tradename
Desoxyn, others
Drug.pregnancy_AU
X
Drug.pregnancy_AU_comment
The system is developed for medicine that can be prescribed, but the equivalent is category X.

via Wikipedia infobox

Chemical data

Formula
C10H15N
Molecular weight
149.23 g/mol
IUPAC name
(2S)-N-methyl-1-phenylpropan-2-amine
SMILES
C[C@@H](CC1=CC=CC=C1)NC
InChIKey
MYWUZJCMWCOHBA-VIFPVBQESA-N
XLogP
2.1
Polar surface area
12 Ų
H-bond donors
1
H-bond acceptors
1
Formal charge
0

via PubChem

Research

180 papers

via PubMed

~45 min read

Encyclopedic overview

39 sections
Contents
  • Uses
  • Medical
  • Recreational
  • Contraindications
  • Adverse effects
  • Physical
  • Cardiovascular
  • Other physical effects
  • Dental and oral health ("meth mouth")
  • Sexually transmitted infection
  • Psychological
  • Neurotoxicity
  • Addiction
  • Epigenetic factors
  • Treatment and management
  • Dependence and withdrawal
  • Neonatal
  • Overdose
  • Psychosis
  • Death from overdose
  • Emergency treatment
  • Interactions
  • Pharmacology
  • Pharmacodynamics
  • Pharmacokinetics
  • Detection in biological fluids
  • Chemistry
  • Degradation
  • Synthesis
  • History, society, and culture
  • Trafficking
  • Legal status
  • Research
  • See also
  • Footnotes
  • Reference notes
  • References
  • Further reading
  • External links

Methamphetamine is a central nervous system (CNS) stimulant that is primarily used as a recreational or performance-enhancing drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder (ADHD). It has also been researched as a potential treatment for traumatic brain injury. Methamphetamine was discovered in 1893 and exists as two enantiomers: levo-methamphetamine and dextro-methamphetamine. Methamphetamine properly refers to a specific chemical substance, the racemic free base, which is an equal mixture of levomethamphetamine and dextromethamphetamine in their pure amine forms, but the hydrochloride salt, commonly called crystal meth, is widely used. Methamphetamine is rarely prescribed over concerns involving its potential for misuse as an aphrodisiac and euphoriant, among other concerns, as well as the availability of other drugs with comparable effects and treatment efficacy such as dextroamphetamine and lisdexamfetamine. While pharmaceutical formulations of methamphetamine in the United States are labeled as methamphetamine hydrochloride, they contain dextromethamphetamine as the active ingredient. Dextromethamphetamine is a stronger CNS stimulant than levomethamphetamine.

Both racemic methamphetamine and dextromethamphetamine are illicitly trafficked and sold owing to their potential for recreational use and ease of manufacture. The highest prevalence of illegal methamphetamine use occurs in parts of Asia and Oceania, and in the United States, where racemic methamphetamine and dextromethamphetamine are classified as Schedule II controlled substances. Levomethamphetamine is available as an over-the-counter (OTC) drug for use as an inhaled nasal decongestant in the United States and is seldom abused. Internationally, the production, distribution, sale, and possession of methamphetamine is restricted or banned in many countries, owing to its placement in schedule II of the United Nations Convention on Psychotropic Substances treaty. While dextromethamphetamine is a more potent drug, racemic methamphetamine is illicitly produced more often, owing to the relative ease of synthesis and regulatory limits of chemical precursor availability.

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

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