Misplaced Pages

4-Methylamphetamine: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editNext edit →Content deleted Content addedVisualWikitext
Revision as of 22:08, 7 November 2016 editThe Voidwalker (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers6,865 editsm rv, requested by bot owner at WP:AN← Previous edit Revision as of 22:31, 7 November 2016 edit undoHeadbomb (talk | contribs)Edit filter managers, Autopatrolled, Extended confirmed users, Page movers, File movers, New page reviewers, Pending changes reviewers, Rollbackers, Template editors453,832 editsm →top: clean up, url redundant with pmc, add pmc, and/or remove accessdate if no url using AWBNext edit →
Line 102: Line 102:
More than a dozen deaths have been reported throughout Europe in 2012-2013 after consumption of amphetamine ('speed') contaminated with 4-methylamphetamine. More than a dozen deaths have been reported throughout Europe in 2012-2013 after consumption of amphetamine ('speed') contaminated with 4-methylamphetamine.


Since 4-MA has little, if any, desirable psychoactive properties, researchers doubt the substance was sold as amphetamine on purpose. A contaminated precursor, after synthesis yielding a mixture of amphetamine and 4-MA, seems the logical culprit.<ref>{{Cite journal|title = 4-Methyl-amphetamine: a health threat for recreational amphetamine users|url = http://www.ncbi.nlm.nih.gov/pubmed/23784740|journal = Journal of Psychopharmacology (Oxford, England)|date = 2013-09-01|issn = 1461-7285|pmid = 23784740|pages = 817–822|volume = 27|issue = 9|doi = 10.1177/0269881113487950|first = P.|last = Blanckaert|first2 = Jgc|last2 = van Amsterdam|first3 = Tm|last3 = Brunt|first4 = Jdj|last4 = van den Berg|first5 = F.|last5 = Van Durme|first6 = K.|last6 = Maudens|first7 = Jch|last7 = van Bussel}}</ref> Since 4-MA has little, if any, desirable psychoactive properties, researchers doubt the substance was sold as amphetamine on purpose. A contaminated precursor, after synthesis yielding a mixture of amphetamine and 4-MA, seems the logical culprit.<ref>{{Cite journal|title = 4-Methyl-amphetamine: a health threat for recreational amphetamine users|journal = Journal of Psychopharmacology (Oxford, England)|date = 2013-09-01|issn = 1461-7285|pmid = 23784740|pages = 817–822|volume = 27|issue = 9|doi = 10.1177/0269881113487950|first = P.|last = Blanckaert|first2 = Jgc|last2 = van Amsterdam|first3 = Tm|last3 = Brunt|first4 = Jdj|last4 = van den Berg|first5 = F.|last5 = Van Durme|first6 = K.|last6 = Maudens|first7 = Jch|last7 = van Bussel}}</ref>
* ] * ]
* ] * ]

Revision as of 22:31, 7 November 2016

Pharmaceutical compound
4-Methylamphetamine
Ball-and-stick model of the 4-methylamphetamine molecule
Clinical data
Routes of
administration		Oral, intranasal, injection
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Elimination half-life6-12 hours
ExcretionUrine
Identifiers
IUPAC name
  • 1-(4-methylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H15N
Molar mass149.23 g/mol g·mol
3D model (JSmol)
SMILES
  • NC(Cc1ccc(cc1)C)C
InChI
  • InChI=1S/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3
  • Key:ZDHZDWSHLNBTEB-UHFFFAOYSA-N
  (what is this?)  (verify)

4-Methylamphetamine (4-MA; PAL-313; Aptrol; p-TAP) is a stimulant and anorectic drug of the phenethylamine and amphetamine chemical classes.

In vitro, it acts as a potent and balanced serotonin, norepinephrine, and dopamine releasing agent with Ki affinity values of 53.4nM, 22.2nM, and 44.1nM at the serotonin, norepinephrine, and dopamine transporters, respectively. However, more recent in vivo studies that involved performing microdialysis on rats showed a different trend. These studies showed that 4-methylamphetamine is much more potent at elevating serotonin (~18 x baseline) relative to dopamine (~5 x baseline). The authors speculated that this is because 5-HT release dampens DA release through some mechanism. For example, it was suggested that a possible cause for this could be activation of 5HT2C receptors since this is known to inhibit DA release. In addition there are alternative explanations such as 5-HT release then going on to encourage GABA release, which has an inhibitory effect on DA neurons.

4-MA was investigated as an appetite suppressant in 1952 and was even given a trade name, Aptrol, but development was apparently never completed. More recently it has been reported as a novel designer drug.

In animal studies, 4-MA was shown to have the lowest rate of self-administration out of a range of similar drugs tested (the others being 3-methylamphetamine, 4-fluoroamphetamine, and 3-fluoroamphetamine), likely as a result of having the highest potency for releasing serotonin relative to dopamine.

More than a dozen deaths have been reported throughout Europe in 2012-2013 after consumption of amphetamine ('speed') contaminated with 4-methylamphetamine.

Since 4-MA has little, if any, desirable psychoactive properties, researchers doubt the substance was sold as amphetamine on purpose. A contaminated precursor, after synthesis yielding a mixture of amphetamine and 4-MA, seems the logical culprit.

References

  1. Wee, S.; Anderson, KG; Baumann, MH; Rothman, RB; Blough, BE; Woolverton, WL (2004). "Relationship between the Serotonergic Activity and Reinforcing Effects of a Series of Amphetamine Analogs". Journal of Pharmacology and Experimental Therapeutics. 313 (2): 848–854. doi:10.1124/jpet.104.080101. PMID 15677348.
  2. Di Giovanni, Giuseppe; Esposito, Ennio; Di Matteo, Vincenzo (2010). "Role of Serotonin in Central Dopamine Dysfunction". CNS Neuroscience & Therapeutics. 16 (3): 179–194. doi:10.1111/j.1755-5949.2010.00135.x. PMID 20557570.
  3. Gelvin, EP; McGavack, TH (1952). "2-Amino-1-(p-methylphenyl)-propane (aptrol) as an anorexigenic agent in weight reduction". New York state journal of medicine. 52 (2): 223–6. PMID 14890975.
  4. Wee, S; Anderson, KG; Baumann, MH; Rothman, RB; Blough, BE; Woolverton, WL (2005). "Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs". The Journal of Pharmacology and Experimental Therapeutics. 313 (2): 848–54. doi:10.1124/jpet.104.080101. PMID 15677348.
  5. Baumann, MH; Clark, RD; Woolverton, WL; Wee, S; Blough, BE; Rothman, RB. (Apr 2011). "In vivo effects of amphetamine analogs reveal evidence for serotonergic inhibition of mesolimbic dopamine transmission in the rat". Journal of Pharmacology and Experimental Therapeutics. 337 (1): 218–25. doi:10.1124/jpet.110.176271. PMC 3063744. PMID 21228061.
  6. Blanckaert, P.; van Amsterdam, Jgc; Brunt, Tm; van den Berg, Jdj; Van Durme, F.; Maudens, K.; van Bussel, Jch (2013-09-01). "4-Methyl-amphetamine: a health threat for recreational amphetamine users". Journal of Psychopharmacology (Oxford, England). 27 (9): 817–822. doi:10.1177/0269881113487950. ISSN 1461-7285. PMID 23784740.
Stimulants
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
ATC code: N06B
Antiobesity agents/Anorectics (A08)
Stimulants
Amphetamines and
phenethylamines
Adrenergic agonists
Other
Cannabinoid
antagonists
GLP-1, GIP, and / or
glucagon agonists
DACRAs
5-HT2C
receptor agonists
Absorption inhibitors
Uncouplers
Others
Adrenergic receptor modulators
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
Phenethylamines
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous
Categories: