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Clinical data | |
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Other names | 3',4'-Methylenedioxy-4-methylaminorex |
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Formula | C11H12N2O3 |
Molar mass | 220.228 g·mol−1 |
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3',4'-Methylenedioxy-4-methylaminorex (MDMAR) is arecreationaldesigner drug from thesubstituted aminorex family, withmonoamine-releasing effects.[1][2][3] It is apotentserotonin–norepinephrine–dopamine releasing agent (SNDRA).[1]
Compound | NETooltip Norepinephrine | DATooltip Dopamine | 5-HTTooltip Serotonin | Ref |
---|---|---|---|---|
Phenethylamine | 10.9 | 39.5 | >10,000 | [4][5][6] |
Dextroamphetamine | 6.6–10.2 | 5.8–24.8 | 698–1,765 | [7][8][6][9] |
Dextromethamphetamine | 12.3–14.3 | 8.5–40.4 | 736–1,292 | [7][10][6][9] |
Aminorex | 15.1–26.4 | 9.1–49.4 | 193–414 | [7][11][6][3][9] |
cis-4-MAR | 4.8 | 1.7 | 53.2 | [3][11] |
cis-4,4'-DMAR | 11.8–31.6 | 8.6–24.4 | 17.7–59.9 | [11][1][3] |
trans-4,4'-DMAR | 31.6 | 24.4 | 59.9 | [1][3] |
cis-MDMAR | 14.8 | 10.2 | 43.9 | [1] |
trans-MDMAR | 38.9 | 36.2 | 73.4 | [1] |
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. Theassays were done in rat brainsynaptosomes and humanpotencies may be different. See alsoMonoamine releasing agent § Activity profiles for a larger table with more compounds.Refs:[12][13] |
RESULTS. Methamphetamine and amphetamine potently released NE (IC50s = 14.3 and 7.0 nM) and DA (IC50s = 40.4 nM and 24.8 nM), and were much less potent releasers of 5-HT (IC50s = 740 nM and 1765 nM). Phentermine released all three biogenic amines with an order of potency NE (IC50 = 28.8 nM)> DA (IC50 = 262 nM)> 5-HT (IC50 = 2575 nM). Aminorex released NE (IC50 = 26.4 nM), DA (IC50 = 44.8 nM) and 5-HT (IC50 = 193 nM). Chlorphentermine was a very potent 5-HT releaser (IC50 = 18.2 nM), a weaker DA releaser (IC50 = 935 nM) and inactive in the NE release assay. Chlorphentermine was a moderate potency inhibitor of [3H]NE uptake (Ki = 451 nM). Diethylpropion, which is self-administered, was a weak DA uptake inhibitor (Ki = 15 µM) and NE uptake inhibitor (Ki = 18.1 µM) and essentially inactive in the other assays. Phendimetrazine, which is self-administered, was a weak DA uptake inhibitor (IC50 = 19 µM), a weak NE uptake inhibitor (8.3 µM) and essentially inactive in the other assays.
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