3-Chlorophenmetrazine

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

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]}

The drug has been shown to act as a norepinephrine–dopamine releasing agent (NDRA) with additional weak serotonin release. ^{[1] [2]} Its EC₅₀ Tooltip 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]}

See also

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

References

1. Namjoshi OA, Decker AM, Landavazo A, Partilla JS, Baumann MH, Rothman RB, et al. (2015). "Chemical modifications to alter monoamine releasing activity of phenmetrazine analogs as potential treatments of stimulant addiction". Drug and Alcohol Dependence. 146: e48. doi:10.1016/j.drugalcdep.2014.09.502.
2. US 20130203752,Blough BE, Rothman R, Landavazo A, Page KM, Decker AM,"Phenylmorpholines and analogues thereof",published 8 August 2013,issued 11 April 2017, assigned to National Institutes of Health, U.S. Department of Health and Human Services