2-Phenylmorpholine

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2-Phenylmorpholine
File:2-phenylmorpholine.svg
Clinical data
Other namesPAL-632; PAL632
Drug classNorepinephrine–dopamine releasing agent; Psychostimulant
Identifiers
  • 2-phenylmorpholine
CAS Number
PubChem CID
ChemSpider
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC10H13NO
Molar mass163.220 g·mol−1
3D model (JSmol)
  • C1COC(CN1)C2=CC=CC=C2
  • InChI=1S/C10H13NO/c1-2-4-9(5-3-1)10-8-11-6-7-12-10/h1-5,10-11H,6-8H2
  • Key:ZLNGFYDJXZZFJP-UHFFFAOYSA-N

2-Phenylmorpholine (code name PAL-632) is the parent compound of the substituted phenylmorpholine class of compounds.[1] Examples of 2-phenylmorpholine derivatives (i.e., substituted phenylmorpholines) include phenmetrazine (3-methyl-2-phenylmorpholine), phendimetrazine ((2S,3S)-3,4-dimethyl-2-phenylmorpholine), and pseudophenmetrazine ((2RS,3SR)-3-methyl-2-phenylmorpholine), which are monoamine releasing agents (MRAs) and psychostimulants.[1][2][3][4] 2-Phenylmorpholine itself is a potent norepinephrine–dopamine releasing agent (NDRA) and hence may act as a stimulant similarly.[5]

Monoamine release of 2-phenylmorpholine and related agents (EC50Tooltip Half maximal effective concentration, nM)
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. 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: [2][3]

References

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