Naphthylmorpholine

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Naphthylmorpholine
File:Naphthylmorpholine.svg
Clinical data
Other namesPAL-678; PAL678; 2-(2′-Naphthyl)morpholine; 2-(Naphthalen-2-yl)morpholine
Drug classMonoamine releasing agent
Identifiers
  • 2-naphthalen-2-ylmorpholine
CAS Number
PubChem CID
ChemSpider
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC14H15NO
Molar mass213.280 g·mol−1
3D model (JSmol)
  • C1COC(CN1)C2=CC3=CC=CC=C3C=C2
  • InChI=1S/C14H15NO/c1-2-4-12-9-13(6-5-11(12)3-1)14-10-15-7-8-16-14/h1-6,9,14-15H,7-8,10H2
  • Key:AQOVYDDILDIECZ-UHFFFAOYSA-N

Naphthylmorpholine (code name PAL-678), also known as 2-(2′-naphthyl)morpholine, is a monoamine releasing agent of the arylmorpholine and naphthylethylamine families.[1][2] It is the derivative of 2-phenylmorpholine with a 2-naphthalene ring instead of a phenyl ring.[1][2] Naphthylmorpholine is a close analogue of naphthylmetrazine (PAL-704; a naphthalene analogue of phenmetrazine), but lacks naphthylmetrazine's methyl group at the 3 position of the morpholine ring.[1][2]

The drug is a potent monoamine releasing agent.[1] Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release have not been reported, but it released 92% of serotonin, 88% of norepinephrine, and 79% of dopamine at a concentration of 10,000 nM in rat brain synaptosomes.[1] Hence, it appears to act preferentially as a releaser of serotonin and norepinephrine and to a lesser extent of dopamine.[1]

Monoamine release of naphthylmorpholine and related agents (EC50Tooltip Half maximal effective concentration, nM)
Compound NETooltip Norepinephrine DATooltip Dopamine 5-HTTooltip Serotonin Ref
d-Amphetamine 6.6–10.2 5.8–24.8 698–1,765 [3][4][5][6][7]
Naphthylaminopropane (NAP; PAL-287) 11.1 12.6 3.4 [8][5]
d-Methamphetamine 12.3–14.3 8.5–40.4 736–1,292 [3][9][5][7]
Methylnaphthylaminopropane (MNAP; PAL-1046) 34 10 13 [10][11]
l-Methcathinone 13.1 14.8 1,772 [12][6]
2-Naphthylmethcathinone (BMAPN; βk-MNAP) 94% at 10 μM 34 27 [13][14]
d-Ethylamphetamine 28.8 44.1 333.0 [15][16]
Ethylnaphthylaminopropane (ENAP; PAL-1045) 137 46 a 12 a [10]
2-Phenylmorpholine (PAL-632) 79 86 20,260 [1]
Naphthylmorpholine (PAL-678) 88% at 10 μM 79% at 10 μM 92% at 10 μM [1]
Phenmetrazine 29–50.4 70–131 7,765–>10,000 [17][5][18][1]
Naphthylmetrazine (PAL-704) 203 111 RI (105) [1]
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. Footnotes: a ENAPTooltip Ethylnaphthylaminopropane is a partial releaser of serotonin (EmaxTooltip maximal efficacy = 66%) and dopamine (Emax = 78%). Refs: [19][20]

References

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