File:Methamphetamine_structure.svg · Wikimedia Commons · See Wikimedia Commons
D-methamphetamine
Sign in to saveAlso 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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AI-generated from the Wikipedia summary — may 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- Effects of methamphetamine isomers on d-methamphetamine self-administration and food-maintained responding in male rats.Psychopharmacology · 2019Bardo MT, Denehy ED, Hammerslag LR et al.DOI: 10.1007/s00213-019-05327-8
- Further pharmacological comparison of D-methamphetamine and L-methamphetamine in rats: abuse-related behavioral and physiological indices.Behavioural pharmacology · 2019Xue Z, Siemian JN, Zhu Q et al.DOI: 10.1097/FBP.0000000000000453
- Ventilatory Effects of Fentanyl, Heroin, and d-Methamphetamine, Alone and in Mixtures in Male Rats Breathing Normal Air .The Journal of pharmacology and experimental therapeutics · 2024Hiranita T, Ho NP, France CPDOI: 10.1124/jpet.123.001653
- PET studies of d-methamphetamine pharmacokinetics in primates: comparison with l-methamphetamine and ( --)-cocaine.Journal of nuclear medicine : official publication, Society of Nuclear Medicine · 2007Fowler JS, Kroll C, Ferrieri R et al.DOI: 10.2967/jnumed.107.040279
- The acute effects of d-amphetamine and methamphetamine on attention and psychomotor performance.Psychopharmacology · 2006Silber BY, Croft RJ, Papafotiou K et al.DOI: 10.1007/s00213-006-0410-7
- Role of d-amphetamine and d-methamphetamine as active metabolites of benzphetamine: Evidence from drug discrimination and pharmacokinetic studies in male rhesus monkeys.Pharmacology, biochemistry, and behavior · 2017Banks ML, Snyder RW, Fennell TR et al.DOI: 10.1016/j.pbb.2017.03.008
- Lobeline attenuates d-methamphetamine self-administration in rats.The Journal of pharmacology and experimental therapeutics · 2001Harrod SB, Dwoskin LP, Crooks PA et al.
- The effect of d-methamphetamine on simulated driving performance.Human psychopharmacology · 2012Silber BY, Croft RJ, Downey LA et al.DOI: 10.1002/hup.1238
via PubMed
Wikidata facts
- Mass
- 149.12
- Image
- Crystal Meth.jpg
Show 8 more facts
- Commons category
- Dextromethamphetamine
- chemical formula
- C₁₀H₁₅N
- canonical SMILES
- CC(CC1=CC=CC=C1)NC
- isomeric SMILES
- C[C@@H](CC1=CC=CC=C1)NC
- World Health Organisation international non-proprietary name
- metamfetamine
- defined daily dose
- 15
- nickname
- polboron
- NCI Thesaurus ID
- C61840
Sources (10)
via Wikidata · CC0
~45 min read
Article
39 sectionsContents
- 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.
Gallery (21)
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