Propylamphetamine

Chemical compound From Wikipedia, the free encyclopedia

Propylamphetamine (code name PAL-424; also known as N-propylamphetamine or NPA) is a psychostimulant of the amphetamine family which was never marketed. It was first developed in the 1970s, mainly for research into the metabolism of,[1] and as a comparison tool to, other amphetamines.[2]

Other namesN-Propylamphetamine; NPA; PAL-424
ATC code
  • none
Legal status
  • UK: Not controlled
MetabolismHepatic
Quick facts Clinical data, Other names ...
Propylamphetamine
Ball-and-stick model of the propylamphetamine molecule
Clinical data
Other namesN-Propylamphetamine; NPA; PAL-424
ATC code
  • none
Legal status
Legal status
  • UK: Not controlled
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
  • N-(1-methyl-2-phenylethyl)propan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.215.934 Edit this at Wikidata
Chemical and physical data
FormulaC12H19N
Molar mass177.291 g·mol−1
3D model (JSmol)
  • NC(C)Cc1ccccc1CCC
  • InChI=1S/C12H19N/c1-3-6-11-7-4-5-8-12(11)9-10(2)13/h4-5,7-8,10H,3,6,9,13H2,1-2H3 checkY
  • Key:VMVXCJCVBKWYTF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
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Propylamphetamine is inactive as a dopamine releasing agent in vitro and instead acts as a low-potency dopamine reuptake inhibitor with an IC50Tooltip half-maximal inhibitory concentration of 1,013 nM.[3] The drug can be N-dealkylated to form amphetamine (10–20% excreted in urine after 24 hours).[4][5] A study in rats found propylamphetamine to be approximately 4-fold less potent than amphetamine.[6][7]

More information Compound, NETooltip Norepinephrine ...
Monoamine release of propylamphetamine and related agents (EC50Tooltip Half maximal effective concentration, nM)
CompoundNETooltip NorepinephrineDATooltip Dopamine5-HTTooltip SerotoninRef
Phenethylamine10.939.5>10,000[3][8][9]
d-Amphetamine6.6–10.25.8–24.8698–1,765[10][11][9][12]
d-Methamphetamine12.3–14.38.5–40.4736–1,292[10][13][9][12]
EthylamphetamineND88.5ND[3]
  d-Ethylamphetamine28.844.1333.0[6][14]
PropylamphetamineNDRI (1,013)ND[3]
ButylamphetamineNDIA (>10,000)ND[3]
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. Refs:[15][16]
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See also

References

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