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| Clinical data | |
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| Other names | PAL-632; PAL632 |
| Drug class | Norepinephrine–dopamine releasing agent;Psychostimulant |
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| CAS Number | |
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| ChemSpider | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C10H13NO |
| Molar mass | 163.220 g·mol−1 |
| 3D model (JSmol) | |
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2-Phenylmorpholine (code namePAL-632) is theparent compound of thesubstituted phenylmorpholine class ofcompounds.[1] Examples of 2-phenylmorpholinederivatives (i.e., substituted phenylmorpholines) includephenmetrazine (3-methyl-2-phenylmorpholine),phendimetrazine ((2S,3S)-3,4-dimethyl-2-phenylmorpholine), andpseudophenmetrazine ((2RS,3SR)-3-methyl-2-phenylmorpholine), which aremonoamine releasing agents (MRAs) andpsychostimulants.[1][2][3][4] 2-Phenylmorpholine itself is apotentnorepinephrine–dopamine releasing agent (NDRA) and hence may act as a stimulant similarly.[5]
| Compound | NETooltip Norepinephrine | DATooltip Dopamine | 5-HTTooltip Serotonin | Ref |
|---|---|---|---|---|
| Phenethylamine | 10.9 | 39.5 | >10,000 | [6][7][8] |
| Dextroamphetamine | 6.6–10.2 | 5.8–24.8 | 698–1,765 | [9][10][8][11] |
| Dextromethamphetamine | 12.3–14.3 | 8.5–40.4 | 736–1,292 | [9][12][8][11] |
| 2-Phenylmorpholine | 79 | 86 | 20,260 | [5] |
| Phenmetrazine | 29–50.4 | 70–131 | 7,765–>10,000 | [4][8][13][5] |
| Phendimetrazine | >10,000 | >10,000 | >100,000 | [4][8][11] |
| Pseudophenmetrazine | 514 | >10,000 (RI) | >10,000 | [4] |
| 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:[2][3] | ||||
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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