| Verifiedfields: | changed |
| Verifiedrevid: | 477222632 |
| Iupac Name: | 1-(4-methylphenyl)propan-2-amine |
| Alt2: | Ball-and-stick model of the 4-methylamphetamine molecule |
| Legal Ca: | Schedule I |
| Legal Uk: | Class A |
| Legal De: | Anlage II |
| Legal Us: | Schedule II (isomer of Methamphetamine) |
| Routes Of Administration: | Oral, intranasal, injection, |
| Elimination Half-Life: | 6-12 hours |
| Excretion: | Urine |
| Cas Number: | 64-11-9 |
| Unii: | 9E273KL7HS |
| Atc Prefix: | none |
| Pubchem: | 199116 |
| Chemspiderid: | 172349 |
| Chembl: | 166183 |
| C: | 10 |
| H: | 15 |
| N: | 1 |
| Smiles: | NC(Cc1ccc(cc1)C)C |
| Stdinchi: | 1S/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 |
| Stdinchikey: | ZDHZDWSHLNBTEB-UHFFFAOYSA-N |
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.[1] [4]
More than a dozen deaths were reported throughout Europe in 2012-2013 after consumption of amphetamine ('speed') contaminated with 4-methylamphetamine.[5] [6] [7]