4-Methylamphetamine

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4-methylamphetamine
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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
  • 1-(4-methylphenyl)propan-2-amine
JSmol)
  • NC(Cc1ccc(cc1)C)C
  • InChI=1S/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 checkY
  • Key:ZDHZDWSHLNBTEB-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

4-Methylamphetamine (4-MA; PAL-313; Aptrol; p-TAP) is a

chemical classes
.

In vitro, it acts as a

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-fluoroamphetamine), likely as a result of having the highest potency for releasing serotonin relative to dopamine.[4][5]

More than a dozen deaths were reported throughout Europe in 2012-2013 after consumption of amphetamine ('speed') contaminated with 4-methylamphetamine.[6]

See also

References

  1. S2CID 12135483
    .
  2. PMID 20557570
    .
  3. PMID 14890975
    .
  4. S2CID 12135483
    .
  5. PMID 21228061
    .
  6. S2CID 35436194
    .
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