4-Methylamphetamine
Template:Short description Template:Cs1 config Template:Short description <templatestyles src="Infobox drug/styles.css"/> Script error: No such module "Infobox".Script error: No such module "TemplatePar".Template:Infobox drug/maintenance categories
4-Methylamphetamine (4-MA), also known by the former proposed brand name Aptrol, is a stimulant and anorectic drug of the amphetamine family. It is structurally related to mephedrone (4-methylmethcathinone).
Pharmacology
In vitro, 4-methylamphetamine acts as a potent and well-balanced serotonin, norepinephrine, and dopamine releasing agent (SNDRA) with EC50 values of 53.4Script error: No such module "String".nM, 22.2Script error: No such module "String".nM, and 44.1Script error: No such module "String".nM at the serotonin, norepinephrine, and dopamine transporters, respectively.[1] Receptor interaction data for 4-methylamphetamine have also been reported.[2]
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.[3]
| Compound | NE | DA | 5-HT | Ref |
|---|---|---|---|---|
| Dextroamphetamine | 6.6–10.2 | 5.8–24.8 | 698–1,765 | [4][5][6][7] |
| Dextromethamphetamine | 12.3–14.3 | 8.5–40.4 | 736–1,292 | [4][8][6][7] |
| 4-Methylamphetamine | 22.2 | 44.1 | 53.4 | [1][9][6] |
| 4-Methylmethamphetamine (mephedrine) | 66.9 | 41.3 | 67.4 | [10][11] |
| 4-Methylcathinone (normephedrone) | 100 | 220 | 210 | [12][13][14] |
| 4-Methylmethcathinone (mephedrone) | 58–62.7 | 49.1–51 | 118.3–122 | [8][5][15][16][17] |
| Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [18][19] | ||||
Research
4-MA was investigated as an appetite suppressant in 1952 and was even given a trade name, Aptrol, but development was apparently never completed.[20] 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][21]
Society and culture
More than a dozen deaths were reported throughout Europe in 2012-2013 after consumption of amphetamine ('speed') contaminated with 4-methylamphetamine.[22][23][24]
See also
- 1-(4-Methylphenyl)-2-aminobutane
- 2-Methylamphetamine
- 3-Methylamphetamine
- 4-Methyl-N-methylamphetamine
- 4-Methyl-N-methylcathinone
- 4-Methylphenmetrazine
- 3-Methoxy-4-methylamphetamine
- 3,4-Dimethylamphetamine
- 4-Ethylamphetamine
References
<templatestyles src="Reflist/styles.css" />
- ↑ a b c Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ a b Script error: No such module "Citation/CS1".
- ↑ a b Script error: No such module "Citation/CS1".
- ↑ a b c Script error: No such module "citation/CS1".
- ↑ a b Script error: No such module "citation/CS1".
- ↑ a b Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
Script error: No such module "Check for unknown parameters".
Script error: No such module "Navbox". Script error: No such module "Navbox". Template:Monoamine releasing agents Script error: No such module "navbox". Script error: No such module "Navbox".