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Methamphetamine information


Methamphetamine
A racemic image of the methamphetamine compound
A 3d image of the levo-methamphetamine compound A 3d image of the dextro-methamphetamine compound
Clinical data
Pronunciation/ˌmɛθæmˈfɛtəmn/
(METH-am-FET-ə-meen), /ˌmɛθəmˈfɛtəmn/
(METH-əm-FET-ə-meen), /ˌmɛθəmˈfɛtəmən/
(METH-əm-FET-ə-mən)[1]
Trade namesDesoxyn, Methedrine
Other namesN-methylamphetamine, N,α-dimethylphenethylamine, desoxyephedrine
AHFS/Drugs.comMonograph
License data
  • US FDA: Methamphetamine
Dependence
liability
Physical: None; Psychological: High
Addiction
liability
High
Routes of
administration
Medical: oral (ingestion)
Recreational: oral, intravenous, intramuscular, subcutaneous, vapour inhalation, insufflation, rectal, vaginal
ATC code
  • N06BA03 (WHO)
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • BR: Class A3 (Psychoactive drugs)
  • CA: Schedule I
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • NZ: Class A
  • UK: Class A
  • US: Schedule II
  • UN: Psychotropic Schedule II
Pharmacokinetic data
BioavailabilityOral: 67%[2][3][4][5]
Intranasal: 79%[2][3]
Inhalation: 67–90%[2][3][4]
Intravenous: 100%[2][5]
Protein bindingVaries widely[6]
MetabolismCYP2D6[7][8] and FMO3[9][10]
Onset of actionOral: 3 hours (peak)[2]
Intranasal: <15 minutes[2]
Inhalation: <18 minutes[2][3]
Intravenous: <15 minutes[2]
Elimination half-life9–12 hours (range 5–30 hours) (irrespective of route)[3][2]
Duration of action8–12 hours[4]
ExcretionPrimarily kidney
Identifiers
IUPAC name
  • (RS)-N-methyl-1-phenylpropan-2-amine
CAS Number
  • 537-46-2 checkY
  • (dl)-Methamphetamine hydrochloride: 300-42-5 checkY
PubChem CID
  • 1206
IUPHAR/BPS
  • 4803
DrugBank
  • DB01577 checkY
ChemSpider
  • 1169 checkY
UNII
  • 44RAL3456C
  • (dl)-Methamphetamine hydrochloride: 24GNZ56D62 checkY
KEGG
  • D08187 checkY
ChEBI
  • CHEBI:6809 checkY
ChEMBL
  • ChEMBL1201201 checkY
PDB ligand
  • B40 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID8037128 Edit this at Wikidata
ECHA InfoCard100.007.882 Edit this at Wikidata
Chemical and physical data
FormulaC10H15N
Molar mass149.237 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
Melting point170 °C (338 °F) [11]
Boiling point212 °C (414 °F) at 760 mmHg[11]
SMILES
  • CNC(C)Cc1ccccc1
InChI
  • InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3 checkY
  • Key:MYWUZJCMWCOHBA-UHFFFAOYSA-N checkY
  (verify)

Methamphetamine[note 1] (contracted from N-methylamphetamine) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity.[17] Methamphetamine was discovered in 1893 and exists as two enantiomers: levo-methamphetamine and dextro-methamphetamine.[note 2] 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. It is rarely prescribed over concerns involving human neurotoxicity and potential for recreational use as an aphrodisiac and euphoriant, among other concerns, as well as the availability of safer substitute drugs with comparable treatment efficacy such as Adderall and Vyvanse. 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. 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.[note 3] 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.

In low to moderate doses, methamphetamine can elevate mood, increase alertness, concentration and energy in fatigued individuals, reduce appetite, and promote weight loss. At very high doses, it can induce psychosis, breakdown of skeletal muscle, seizures and bleeding in the brain. Chronic high-dose use can precipitate unpredictable and rapid mood swings, stimulant psychosis (e.g., paranoia, hallucinations, delirium, and delusions) and violent behavior. Recreationally, methamphetamine's ability to increase energy has been reported to lift mood and increase sexual desire to such an extent that users are able to engage in sexual activity continuously for several days while binging the drug.[21] Methamphetamine is known to possess a high addiction liability (i.e., a high likelihood that long-term or high dose use will lead to compulsive drug use) and high dependence liability (i.e. a high likelihood that withdrawal symptoms will occur when methamphetamine use ceases). Withdrawal from methamphetamine after heavy use may lead to a post-acute-withdrawal syndrome, which can persist for months beyond the typical withdrawal period. Methamphetamine is neurotoxic to human midbrain dopaminergic neurons at high doses. Methamphetamine has been shown to have a higher affinity and, as a result, higher toxicity toward serotonergic neurons than amphetamine.[22][23] Methamphetamine neurotoxicity causes adverse changes in brain structure and function, such as reductions in grey matter volume in several brain regions, as well as adverse changes in markers of metabolic integrity.[23]

Methamphetamine belongs to the substituted phenethylamine and substituted amphetamine chemical classes. It is related to the other dimethylphenethylamines as a positional isomer of these compounds, which share the common chemical formula C10H15N.

  1. ^ "methamphetamine". Methamphetamine. Lexico. Archived from the original on 14 June 2021. Retrieved 22 April 2022.
  2. ^ a b c d e f g h i Cite error: The named reference pmid19426289 was invoked but never defined (see the help page).
  3. ^ a b c d e Cite error: The named reference Schep was invoked but never defined (see the help page).
  4. ^ a b c Courtney KE, Ray LA (October 2014). "Methamphetamine: an update on epidemiology, pharmacology, clinical phenomenology, and treatment literature". Drug Alcohol Depend. 143: 11–21. doi:10.1016/j.drugalcdep.2014.08.003. PMC 4164186. PMID 25176528.
  5. ^ a b Rau T, Ziemniak J, Poulsen D (2015). "The neuroprotective potential of low-dose methamphetamine in preclinical models of stroke and traumatic brain injury". Prog. Neuropsychopharmacol. Biol. Psychiatry. 64: 231–6. doi:10.1016/j.pnpbp.2015.02.013. PMID 25724762. In humans, the oral bioavailability of methamphetamine is approximately 70% but increases to 100% following intravenous (IV) delivery (Ares-Santos et al., 2013).
  6. ^ "Toxicity". Methamphetamine. PubChem Compound. National Center for Biotechnology Information.
  7. ^ Sellers EM, Tyndale RF (2000). "Mimicking gene defects to treat drug dependence". Ann. N. Y. Acad. Sci. 909 (1): 233–246. Bibcode:2000NYASA.909..233S. doi:10.1111/j.1749-6632.2000.tb06685.x. PMID 10911933. S2CID 27787938. Methamphetamine, a central nervous system stimulant drug, is p-hydroxylated by CYP2D6 to less active p-OH-methamphetamine.
  8. ^ Cite error: The named reference FDA Pharmacokinetics was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference FMO was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference FMO3-Primary was invoked but never defined (see the help page).
  11. ^ a b "Chemical and Physical Properties". Methamphetamine. PubChem Compound. National Center for Biotechnology Information.
  12. ^ a b "Methamphetamine". Drug profiles. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 8 January 2015. Archived from the original on 15 April 2016. Retrieved 27 November 2018. The term metamfetamine (the International Non-Proprietary Name: INN) strictly relates to the specific enantiomer (S)-N,α-dimethylbenzeneethanamine.
  13. ^ "Identification". Methamphetamine. DrugBank. University of Alberta. 8 February 2013.
  14. ^ "Methedrine (methamphetamine hydrochloride): Uses, Symptoms, Signs and Addiction Treatment". Addictionlibrary.org. Archived from the original on 4 March 2016. Retrieved 16 January 2016.
  15. ^ "Meth Slang Names". MethhelpOnline. Archived from the original on 7 December 2013. Retrieved 1 January 2014.
  16. ^ "Methamphetamine and the law". Archived from the original on 28 January 2015. Retrieved 30 December 2014.
  17. ^ Yu S, Zhu L, Shen Q, Bai X, Di X (March 2015). "Recent advances in methamphetamine neurotoxicity mechanisms and its molecular pathophysiology". Behav. Neurol. 2015: 103969. doi:10.1155/2015/103969. PMC 4377385. PMID 25861156. In 1971, METH was restricted by US law, although oral METH (Ovation Pharmaceuticals) continues to be used today in the USA as a second-line treatment for a number of medical conditions, including attention deficit hyperactivity disorder (ADHD) and refractory obesity [3].
  18. ^ "Levomethamphetamine". Pubchem Compound. National Center for Biotechnology Information. Archived from the original on 6 October 2014. Retrieved 27 November 2018.
  19. ^ "Part 341 – cold, cough, allergy, bronchodilator, and antiasthmatic drug products for over-the-counter human use". Code of Federal Regulations Title 21: Subchapter D – Drugs for human use. United States Food and Drug Administration. April 2015. Topical nasal decongestants --(i) For products containing levmetamfetamine identified in 341.20(b)(1) when used in an inhalant dosage form. The product delivers in every 800 milliliters of air 0.04 to 0.150 milligrams of levmetamfetamine.
  20. ^ "Identification". Levomethamphetamine. Pubchem Compound. National Center for Biotechnology Information.
  21. ^ "Meth's aphrodisiac effect adds to drug's allure". NBC News. Associated Press. 3 December 2004. Archived from the original on 12 August 2013. Retrieved 12 September 2019.
  22. ^ Yu S, Zhu L, Shen Q, Bai X, Di X (2015). "Recent advances in methamphetamine neurotoxicity mechanisms and its molecular pathophysiology". Behav Neurol. 2015: 1–11. doi:10.1155/2015/103969. PMC 4377385. PMID 25861156.
  23. ^ a b Cite error: The named reference pmid19328213 was invoked but never defined (see the help page).


Cite error: There are <ref group=note> tags on this page, but the references will not show without a {{reflist|group=note}} template (see the help page).

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