3-Chlorophenmetrazine

3-Chlorophenmetrazine (3-CPM; code name PAL-594) is a recreational designer drug with stimulant effects.^[1][2] It is a substituted phenylmorpholine derivative, closely related to better known drugs such as phenmetrazine and 3-fluorophenmetrazine (3-FPM; PAL-593).^[1][2]

Other names3-CPM; PAL-594; PAL594

CAS Number

• 1097796-78-5 ^Y

PubChem CID

• 43350791

ChemSpider

• 27935393

Quick facts Clinical data, Other names ...

3-Chlorophenmetrazine

Clinical data
Other names	3-CPM; PAL-594; PAL594
Identifiers
IUPAC name 3-methyl-2-(3-chlorophenyl)morpholine
CAS Number	1097796-78-5 Y
PubChem CID	43350791
ChemSpider	27935393
UNII	B6P88Q2VW5
CompTox Dashboard (EPA)	DTXSID701337061
Chemical and physical data
Formula	C11H14ClNO
Molar mass	211.69 g·mol−1
3D model (JSmol)	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,5-6H2,1H3 Key:BOFUZZAQNVYZFF-UHFFFAOYSA-N

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The drug has been shown to act as a norepinephrine–dopamine releasing agent (NDRA) with additional weak serotonin release.^[1][2] 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.^[1][2] Hence, it releases dopamine about 3-fold more potently than norepinephrine and about 11-fold more potently than serotonin.^[1][2]

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.^[1][2]