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  3. Propylamphetamine - Wikipedia
Propylamphetamine - Wikipedia
From Wikipedia, the free encyclopedia
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)

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]

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]

Monoamine release of propylamphetamine and related agents (EC50Tooltip Half maximal effective concentration, nM)
Compound NETooltip Norepinephrine DATooltip Dopamine 5-HTTooltip Serotonin Ref
Phenethylamine 10.9 39.5 >10,000 [3][8][9]
d-Amphetamine 6.6–10.2 5.8–24.8 698–1,765 [10][11][9][12]
d-Methamphetamine 12.3–14.3 8.5–40.4 736–1,292 [10][13][9][12]
Ethylamphetamine ND 88.5 ND [3]
  d-Ethylamphetamine 28.8 44.1 333.0 [6][14]
Propylamphetamine ND RI (1,013) ND [3]
Butylamphetamine ND IA (>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]

See also

References

  1. ^ Nazarali AJ, Baker GB, Coutts RT, Pasutto FM (1983). "Amphetamine in rat brain after intraperitoneal injection of N-alkylated analogues". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 7 (4–6): 813–6. doi:10.1016/0278-5846(83)90073-8. PMID 6686713. S2CID 35531794.
  2. ^ Valtier S, Cody JT (October 1995). "Evaluation of internal standards for the analysis of amphetamine and methamphetamine". Journal of Analytical Toxicology. 19 (6): 375–80. doi:10.1093/jat/19.6.375. PMID 8926730.
  3. ^ a b c d e Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.
  4. ^ Beckett AH, Shenoy EV (October 1973). "The effect of N-alkyl chain length of stereochemistry on the absorption, metabolism and during excretion of N-alkylamphetamines in man". J Pharm Pharmacol. 25 (10): 793–799. doi:10.1111/j.2042-7158.1973.tb09943.x. PMID 4151673.
  5. ^ Coutts RT, Dawson GW, Beckett AH (November 1976). "In vitro metabolism of 1-phenyl-2-(n-propylamino) propane (N-propylamphetamine) by rat liver homogenates". J Pharm Pharmacol. 28 (11): 815–821. doi:10.1111/j.2042-7158.1976.tb04063.x. PMID 11289.
  6. ^ a b Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, Baumann MH, Fantegrossi WE (March 2024). "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". Neuropharmacology. 245 109827. doi:10.1016/j.neuropharm.2023.109827. PMC 10842458. PMID 38154512. Although the number of amphetamine analogues with different amine substituents is relatively low in recreational drug markets (Cho and Segal, 1994), N-methyl and N-ethyl substitutions are sometimes found. Pharmacological activity of amphetamine-type drugs is decreased substantially if the N-alkyl chain is lengthened beyond ethyl, as previous studies show that N-propylamphetamine and N-butylamphetamine are ~4-fold and ~6-fold less potent than amphetamine in rats (Woolverton et al., 1980).
  7. ^ Woolverton WL, Shybut G, Johanson CE (December 1980). "Structure-activity relationships among some d-N-alkylated amphetamines". Pharmacology, Biochemistry, and Behavior. 13 (6): 869–876. CiteSeerX 10.1.1.687.9187. doi:10.1016/0091-3057(80)90221-x. PMID 7208552. S2CID 25123820.
  8. ^ Forsyth, Andrea N (22 May 2012). "Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines". ScholarWorks@UNO. Retrieved 4 November 2024.
  9. ^ a b c Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
  10. ^ a b Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse. 39 (1): 32–41. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707. S2CID 15573624.
  11. ^ Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW (March 2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology. 38 (4): 552–562. doi:10.1038/npp.2012.204. PMC 3572453. PMID 23072836.
  12. ^ a b Partilla JS, Dersch CM, Baumann MH, Carroll FI, Rothman RB (1999). "Profiling CNS Stimulants with a High-Throughput Assay for Biogenic Amine Transporter Substrates". Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc (PDF). NIDA Res Monogr. Vol. 180. pp. 1–476 (252). PMID 11680410. Archived from the original (PDF) on August 5, 2023. RESULTS. Methamphetamine and amphetamine potently released NE (IC50s = 14.3 and 7.0 nM) and DA (IC50s = 40.4 nM and 24.8 nM), and were much less potent releasers of 5-HT (IC50s = 740 nM and 1765 nM). [...]
  13. ^ Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV (April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology. 37 (5): 1192–1203. doi:10.1038/npp.2011.304. PMC 3306880. PMID 22169943.
  14. ^ Nicole, Lauren (2022). "In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones". ProQuest. Retrieved 5 December 2024. FIGURE 2-6: Release: Effects of the specified test drug on monoamine release by DAT (red circles), NET (blue squares), and SERT (black traingles) in rat brain tissue. [...] EC50 values determined for the drug indicated within the panel. [...]
  15. ^ Rothman RB, Baumann MH (October 2003). "Monoamine transporters and psychostimulant drugs". European Journal of Pharmacology. 479 (1–3): 23–40. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135.
  16. ^ Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
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