2-Phenylmorpholine

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 ;
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;

2-Phenylmorpholine (code name PAL-632) is the parent compound of the substituted phenylmorpholine class of compounds. 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. 2-Phenylmorpholine itself is a potent norepinephrine–dopamine releasing agent (NDRA) and hence may act as a stimulant similarly.

Monoamine release of 2-phenylmorpholine and related agents (EC₅₀Tooltip Half maximal effective concentration, nM)
Compound	NETooltip Norepinephrine	DATooltip Dopamine	5-HTTooltip Serotonin
Phenethylamine	10.9	39.5	>10,000
Dextroamphetamine	6.6–10.2	5.8–24.8	698–1,765
Dextromethamphetamine	12.3–14.3	8.5–40.4	736–1,292
2-Phenylmorpholine	79	86	20,260
Phenmetrazine	29–50.4	70–131	7,765–>10,000
Phendimetrazine	>10,000	>10,000	>100,000
Pseudophenmetrazine	514	>10,000 (RI)	>10,000
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: