Phenylbutenamine

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| image = Phenylbutenamine.svg

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| class = Norepinephrine–dopamine releasing agent

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| PubChem = 179624

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| ChemSpiderID = 28545154

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| synonyms = 4-Phenylbut-3-en-2-amine; 1-Methyl-3-phenylprop-2-enylamine; PAL-881/PAL-893

| IUPAC_name = 4-phenylbut-3-en-2-amine

| C=10 | H=13 | N=1

| StdInChI=1S/C10H13N/c1-9(11)7-8-10-5-3-2-4-6-10/h2-9H,11H2,1H3

| StdInChIKey = QPVUUOXSCVQZQG-UHFFFAOYSA-N

| SMILES = CC(C=CC1=CC=CC=C1)N

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Phenylbutenamine, or 4-phenylbut-3-en-2-amine, is a monoamine releasing agent (MRA) of the arylalkylamine family related to β-phenethylamine and amphetamine.{{cite journal | vauthors = Decker AM, Partilla JS, Baumann MH, Rothman RB, Blough BE | title=The biogenic amine transporter activity of vinylogous amphetamine analogs | journal=MedChemComm | volume=7 | issue=8 | date=2016 | issn=2040-2503 | doi=10.1039/C6MD00245E | pages=1657–1663}}{{cite patent | country = US | number = 10899699 | title=Vinylogous phenethylamines as neurotransmitter releasers | inventor = Blough B, Decker A, Rothman R | assign = RTI International Inc. | gdate = 26 January 2021 | url=https://patents.google.com/patent/US10899699B2/en }} It has two possible stereoisomers: (3E)-phenylbutenamine (PAL-881) and (3Z)-phenylbutenamine (PAL-893). Both of these enantiomers act as norepinephrine–dopamine releasing agents (NDRAs), and to similar comparative extents, albeit with far lower potency than β-phenethylamine or amphetamine.{{cite book | vauthors = Blough B | chapter = Dopamine-releasing agents | veditors = Trudell ML, Izenwasser S | title = Dopamine Transporters: Chemistry, Biology and Pharmacology | pages = 305–320 | date = July 2008 | isbn = 978-0-470-11790-3 | oclc = 181862653 | ol = OL18589888W | publisher = Wiley | location = Hoboken [NJ] | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}