2-Phenylmorpholine

Pharmaceutical compound From Wikipedia, the free encyclopedia

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]

More information Compound, NETooltip Norepinephrine ...
Monoamine release of 2-phenylmorpholine and related agents (EC50Tooltip Half maximal effective concentration, nM)
CompoundNETooltip NorepinephrineDATooltip Dopamine5-HTTooltip SerotoninRef
Phenethylamine10.939.5>10,000[6][7][8]
Dextroamphetamine6.6–10.25.8–24.8698–1,765[9][10][8][11]
Dextromethamphetamine12.3–14.38.5–40.4736–1,292[9][12][8][11]
2-Phenylmorpholine798620,260[5]
Phenmetrazine29–50.470–1317,765–>10,000[4][8][13][5]
Phendimetrazine>10,000>10,000>100,000[4][8][11]
Pseudophenmetrazine514>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]
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Other namesPAL-632; PAL632
CAS Number
Quick facts Clinical data, Other names ...
2-Phenylmorpholine
Clinical data
Other namesPAL-632; PAL632
Drug classNorepinephrine–dopamine releasing agent; Psychostimulant
Identifiers
  • 2-phenylmorpholine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
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
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References

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