Propylamphetamine
{{Short description|Chemical compound}}
{{Infobox drug
| Verifiedfields = changed
| verifiedrevid = 464217299
| IUPAC_name = N-(1-methyl-2-phenylethyl)propan-1-amine
| image = N-Propylamphetamine.svg
| image_class = skin-invert-image
| width =
| image2 = Propylamphetamine molecule ball.png
| width2 =
| alt2 = Ball-and-stick model of the propylamphetamine molecule
| legal_UK = Not controlled
| tradename =
| metabolism = Hepatic
| excretion = Renal
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 51799-32-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E52ZLB6J7C
| ATC_prefix = none
| PubChem = 103544
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11655332
| synonyms = N-Propylamphetamine; NPA; PAL-424
| C=12 | H=19 | N=1
| smiles = NC(C)Cc1ccccc1CCC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VMVXCJCVBKWYTF-UHFFFAOYSA-N
}}
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,{{cite journal | vauthors = Nazarali AJ, Baker GB, Coutts RT, Pasutto FM | title = Amphetamine in rat brain after intraperitoneal injection of N-alkylated analogues | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 7 | issue = 4–6 | pages = 813–6 | year = 1983 | pmid = 6686713 | doi = 10.1016/0278-5846(83)90073-8 | s2cid = 35531794 }} and as a comparison tool to, other amphetamines.{{cite journal | vauthors = Valtier S, Cody JT | title = Evaluation of internal standards for the analysis of amphetamine and methamphetamine | journal = Journal of Analytical Toxicology | volume = 19 | issue = 6 | pages = 375–80 | date = October 1995 | pmid = 8926730 | doi = 10.1093/jat/19.6.375 }}
Propylamphetamine is inactive as a dopamine releasing agent in vitro and instead acts as a low-potency dopamine reuptake inhibitor with an {{Abbrlink|IC50|half-maximal inhibitory concentration}} of 1,013{{nbsp}}nM.{{cite journal | vauthors = Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL | title = Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter | journal = Drug Alcohol Depend | volume = 147 | issue = | pages = 1–19 | date = February 2015 | pmid = 25548026 | doi = 10.1016/j.drugalcdep.2014.12.005 | url = | pmc = 4297708 }} The drug can be N-dealkylated to form amphetamine (10–20% excreted in urine after 24{{nbsp}}hours).{{cite journal | vauthors = Beckett AH, Shenoy EV | title = The effect of N-alkyl chain length of stereochemistry on the absorption, metabolism and during excretion of N-alkylamphetamines in man | journal = J Pharm Pharmacol | volume = 25 | issue = 10 | pages = 793–799 | date = October 1973 | pmid = 4151673 | doi = 10.1111/j.2042-7158.1973.tb09943.x | url = }}{{cite journal | vauthors = Coutts RT, Dawson GW, Beckett AH | title = In vitro metabolism of 1-phenyl-2-(n-propylamino) propane (N-propylamphetamine) by rat liver homogenates | journal = J Pharm Pharmacol | volume = 28 | issue = 11 | pages = 815–821 | date = November 1976 | pmid = 11289 | doi = 10.1111/j.2042-7158.1976.tb04063.x | url = }} A study in rats found propylamphetamine to be approximately 4-fold less potent than amphetamine.{{cite journal | vauthors = Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, Baumann MH, Fantegrossi WE | title = Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones | journal = Neuropharmacology | volume = 245 | issue = | pages = 109827 | date = March 2024 | pmid = 38154512 | doi = 10.1016/j.neuropharm.2023.109827 | pmc = 10842458 | url = | quote = 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).}}{{cite journal | vauthors = Woolverton WL, Shybut G, Johanson CE | title = Structure-activity relationships among some d-N-alkylated amphetamines | journal = Pharmacology, Biochemistry, and Behavior | volume = 13 | issue = 6 | pages = 869–876 | date = December 1980 | pmid = 7208552 | doi = 10.1016/0091-3057(80)90221-x | citeseerx = 10.1.1.687.9187 | s2cid = 25123820 }}
See also
References
{{Reflist}}
{{Stimulants}}
{{Monoamine releasing agents}}
{{Phenethylamines}}