2-Phenylmorpholine

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]

2-Phenylmorpholine

Clinical data
Other names	PAL-632; PAL632
Drug class	Norepinephrine–dopamine releasing agent; Psychostimulant
Identifiers
IUPAC name 2-phenylmorpholine
CAS Number	23972-41-0 Y
PubChem CID	91101
ChemSpider	82261
ChEMBL	ChEMBL4069068
CompTox Dashboard (EPA)	DTXSID70946825
Chemical and physical data
Formula	C10H13NO
Molar mass	163.220 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1COC(CN1)C2=CC=CC=C2
InChI 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