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| Formula | C11H15NO |
| Molar mass | 177.247 g·mol−1 |
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Pseudophenmetrazine is apsychostimulant of thephenylmorpholine group. It is theN-demethylated andcis-configuredanalogue ofphendimetrazine as well as thecis-configuredstereoisomer ofphenmetrazine.[1] In addition, along with phenmetrazine, it is believed to be one of theactive metabolites of phendimetrazine, which itself isinactive and behaves merely as aprodrug.[2]
Relative to phenmetrazine, pseudophenmetrazine is of fairly lowpotency, acting as a modestreleasing agent ofnorepinephrine (EC50 = 514 nM), while its (+)-enantiomer is a weak releaser ofdopamine (EC50 = 1,457 nM) whereas its (−)-enantiomer is a weakreuptake inhibitor of dopamine (Ki = 2,691 nM);[2][3] together as aracemic mixture with the two enantiomers combined, pseudophenmetrazine behaves overall more as adopamine reuptake inhibitor (Ki = 2,630 nM),[2][3] possibly due to the (+)-enantiomer blocking theuptake of the (−)-enantiomer intodopaminergicneurons and thus preventing it from inducing dopamine release. Neither enantiomer has any significant effect onserotonin reuptake or release (both Ki = >10,000 nM and EC50 = >10,000 nM, respectively).[2][3]
| 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] |
| 2-Phenylmorpholine | 79 | 86 | 20,260 | [11] |
| Phenmetrazine | 29–50.4 | 70–131 | 7,765–>10,000 | [12][6][13][11] |
| (+)-Phenmetrazine | 37.5 | 87.4 | 3246 | [12] |
| (–)-Phenmetrazine | 62.9 | 415 | >10,000 | [12] |
| Phendimetrazine | >10,000 | >10,000 | >100,000 | [12][6][9] |
| Pseudophenmetrazine | 514 | >10,000 (RI) | >10,000 | [12] |
| (+)-Pseudophenmetrazine | 349 | 1,457 | >10,000 | [12] |
| (–)-Pseudophenmetrazine | 2,511 | IA (RI) | >10,000 | [12] |
| 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:[14][15] | ||||
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.
