Phenylbutenamine

Phenylbutenamine
Clinical data
Other names	4-Phenylbut-3-en-2-amine; 1-Methyl-3-phenylprop-2-enylamine; PAL-881/PAL-893
Drug class	Norepinephrine–dopamine releasing agent
Identifiers
	IUPAC name 4-phenylbut-3-en-2-amine;
PubChem CID	179624;
ChemSpider	28545154;
Chemical and physical data
Formula	C10H13N
Molar mass	147.221 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C=CC1=CC=CC=C1)N;
	InChI InChI=1S/C10H13N/c1-9(11)7-8-10-5-3-2-4-6-10/h2-9H,11H2,1H3; Key:QPVUUOXSCVQZQG-UHFFFAOYSA-N;

Phenylbutenamine, or 4-phenylbut-3-en-2-amine, is a monoamine releasing agent (MRA) of the arylalkylamine family related to β-phenethylamine and amphetamine.^[1]^[2] It has two possible stereoisomers: (3E)-phenylbutenamine (PAL-881) and (3Z)-phenylbutenamine (PAL-893).^[1]^[2] 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.^[1]^[2]^[3]

References

^ ^a ^b ^c ^d Decker AM, Partilla JS, Baumann MH, Rothman RB, Blough BE (2016). "The biogenic amine transporter activity of vinylogous amphetamine analogs". MedChemComm. 7 (8): 1657–1663. doi:10.1039/C6MD00245E. ISSN 2040-2503.
^ ^a ^b ^c ^d US 10899699, Blough B, Decker A, Rothman R, "Vinylogous phenethylamines as neurotransmitter releasers", issued 26 January 2021, assigned to RTI International Inc.
^ 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.

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