4-Methylamphetamine

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4-Methylamphetamine
4-Methylamphetamine.svg
Ball-and-stick model of the 4-methylamphetamine molecule
Systematic (IUPAC) name
1-(4-methylphenyl)propan-2-amine
Clinical data
Routes of
administration
Oral, intranasal, injection
Legal status
Legal status
Pharmacokinetic data
Biological half-life 6-12 hours
Excretion Urine
Identifiers
CAS Number 22683-78-9 N
ATC code none
PubChem CID 199116
ChemSpider 172349 YesY
ChEMBL CHEMBL166183 YesY
Chemical data
Formula C10H15N
Molar mass 149.23 g/mol
 NYesY (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.[1] 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.[2]

4-MA was investigated as an appetite suppressant in 1952 and was even given a trade name, Aptrol, but development was apparently never completed.[3] 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.[4][5]

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.[6]

References[edit]

  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 3063744free to read. 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.