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3-Chlorophenmetrazine

3-Chlorophenmetrazine (3-CPM; code name PAL-594) is a recreational designer drug with stimulant effects. It is a substituted phenylmorpholine derivative, closely related to better known drugs such as phenmetrazine and 3-fluorophenmetrazine (3-FPM; PAL-593).


Column 1
3-CPM; PAL-594; PAL594
IUPAC name
3-methyl-2-(3-chlorophenyl)morpholine
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43350791
27935393
B6P88Q2VW5
DTXSID701337061
C11H14ClNO
211.69 g·mol−1
Interactive image
SMILES
CC1C(OCCN1)C2=CC(=CC=C2)Cl
InChI
InChI=1S/C11H14ClNO/c1-8-11(14-6-5-13-8)9-3-2-4-10(12)7-9/h2-4,7-8,11,13H,5-6H2,1H3Key:BOFUZZAQNVYZFF-UHFFFAOYSA-N

3-Chlorophenmetrazine (3-CPM; code name PAL-594) is a recreational designer drug with stimulant effects. It is a substituted phenylmorpholine derivative, closely related to better known drugs such as phenmetrazine and 3-fluorophenmetrazine (3-FPM; PAL-593).

The drug has been shown to act as a norepinephrine–dopamine releasing agent (NDRA) with additional weak serotonin release. Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release are 27 nM for dopamine, 75 nM for norepinephrine, and 301 nM for serotonin in rat brain synaptosomes. Hence, it releases dopamine about 3-fold more potently than norepinephrine and about 11-fold more potently than serotonin.

Similarly to cis-4-methylaminorex, the drug is notable in being one of the most selective dopamine releasing agents (DRAs) known, although it still has substantial capacity to release norepinephrine.

  • 3-Bromomethylphenidate
  • 3-Chloromethamphetamine
  • 3-Chloromethcathinone
  • 4-Methylphenmetrazine
  • G-130
  • Methylenedioxyphenmetrazine
  • Phendimetrazine
  • PDM-35
  • Radafaxine
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