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3-Chlorophenmetrazine

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
3-Chlorophenmetrazine
Clinical data
Other names3-CPM; PAL-594; PAL594
Identifiers
  • 3-methyl-2-(3-chlorophenyl)morpholine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H14ClNO
Molar mass211.69 g·mol−1
3D model (JSmol)
  • CC1C(OCCN1)C2=CC(=CC=C2)Cl
  • 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 namePAL-594) is arecreationaldesigner drug withstimulant effects.[1][2] It is asubstituted phenylmorpholinederivative, closely related to better known drugs such asphenmetrazine and3-fluorophenmetrazine (3-FPM; PAL-593).[1][2]

The drug has been shown to act as anorepinephrine–dopamine releasing agent (NDRA) with additional weakserotonin release.[1][2] ItsEC50Tooltip half-maximal effective concentration values for induction ofmonoamine release are 27 nM fordopamine, 75 nM fornorepinephrine, and 301 nM for serotonin in rat brainsynaptosomes.[1][2] Hence, it releases dopamine about 3-fold morepotently than norepinephrine and about 11-fold more potently than serotonin.[1][2]

Similarly tocis-4-methylaminorex, the drug is notable in being one of the mostselectivedopamine releasing agents (DRAs) known, although it still has substantial capacity to release norepinephrine.[1][2]

See also

[edit]

References

[edit]
  1. ^abcdefNamjoshi 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. ^abcdefUS 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 
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Phenethylpyrrolidines
Racetams
Psychedelics
Tropanes
Tryptamines
Others
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
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