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| Other names | N-Propylamphetamine; NPA; PAL-424 |
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| Pharmacokinetic data | |
| Metabolism | Hepatic |
| Excretion | Renal |
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| ECHA InfoCard | 100.215.934 |
| Chemical and physical data | |
| Formula | C12H19N |
| Molar mass | 177.291 g·mol−1 |
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Propylamphetamine (code namePAL-424; also known asN-propylamphetamine orNPA) is apsychostimulant of theamphetamine family which was never marketed. It was firstdeveloped in the 1970s, mainly forresearch into themetabolism of,[1] and as a comparison tool to, other amphetamines.[2]
Propylamphetamine is inactive as adopamine releasing agentin vitro and instead acts as a low-potencydopamine reuptake inhibitor with anIC50Tooltip half-maximal inhibitory concentration of 1,013 nM.[3] The drug can beN-dealkylated to formamphetamine (10–20%excreted inurine after 24 hours).[4][5] A study in rats found propylamphetamine to be approximately 4-fold lesspotent thanamphetamine.[6][7]
| Compound | NETooltip Norepinephrine | DATooltip Dopamine | 5-HTTooltip Serotonin | Ref | ||
|---|---|---|---|---|---|---|
| Phenethylamine | 10.9 | 39.5 | >10,000 | [3][8][9] | ||
| d-Amphetamine | 6.6–10.2 | 5.8–24.8 | 698–1,765 | [10][11][9][12] | ||
| d-Methamphetamine | 12.3–14.3 | 8.5–40.4 | 736–1,292 | [10][13][9][12] | ||
| Ethylamphetamine | ND | 88.5 | ND | [3] | ||
| d-Ethylamphetamine | 28.8 | 44.1 | 333.0 | [6][14] | ||
| Propylamphetamine | ND | RI (1,013) | ND | [3] | ||
| Butylamphetamine | ND | IA (>10,000) | ND | [3] | ||
| 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:[15][16] | ||||||
Although the number of amphetamine analogues with different amine substituents is relatively low in recreational drug markets (Cho and Segal, 1994), N-methyl and N-ethyl substitutions are sometimes found. Pharmacological activity of amphetamine-type drugs is decreased substantially if the N-alkyl chain is lengthened beyond ethyl, as previous studies show that N-propylamphetamine and N-butylamphetamine are ~4-fold and ~6-fold less potent than amphetamine in rats (Woolverton et al., 1980).
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). [...]
FIGURE 2-6: Release: Effects of the specified test drug on monoamine release by DAT (red circles), NET (blue squares), and SERT (black traingles) in rat brain tissue. [...] EC50 values determined for the drug indicated within the panel. [...]