Phenylpropylamine

Not to be confused with 2-Phenylpropylamine.

Phenylpropylamine, also known as 3-phenylpropylamine, is a monoamine releasing agent (MRA) related to phenethylamine (2-phenylethylamine).^[1][2] It is the analogue of phenethylamine in which the ethylamine side chain has been lengthened by one carbon atom to instead be a propylamine chain.^[1][2]

Phenylpropylamine

Clinical data
Other names	3-Phenyl-1-propylamine
Drug class	Norepinephrine–dopamine releasing agent
Identifiers
IUPAC name 3-phenylpropan-1-amine
CAS Number	2038-57-5
PubChem CID	16259
DrugBank	DB04410
ChemSpider	15427
UNII	P8326EZ31P
ChEBI	CHEBI:45017
ChEMBL	ChEMBL276864
CompTox Dashboard (EPA)	DTXSID10174307
ECHA InfoCard	100.016.376
Chemical and physical data
Formula	C9H13N
Molar mass	135.210 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)CCCN
InChI InChI=1S/C9H13N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8,10H2 Key:LYUQWQRTDLVQGA-UHFFFAOYSA-N

Phenylpropylamine was synthesized and characterized during investigations of the structure–activity relationships (SAR) of phenethylamine and amphetamine MRAs.^[1][2] It acts as a norepinephrine–dopamine releasing agent (NDRA).^[1][2] However, phenylpropylamine is dramatically less potent than phenethylamine as an NDRA in rat brain synaptosomes in vitro and shows ~7-fold preference for induction of norepinephrine release over dopamine release.^[1][2]

The analogue of phenethylamine with the ethylamine side chain shortened by one carbon atom to instead be a methylamine chain is benzylamine (phenylmethylamine).^[3] In contrast to phenethylamine and phenylpropylamine, benzylamine is said to be inactive as a norepinephrine releasing agent (NRA).^[3] However, certain derivatives of benzylamine have nonetheless been found to show MRA-like effects in animals.^[4][5] In addition, benzylpiperazine, an analogue of benzylamine with a methylamine-like side chain, is a potent MRA and psychostimulant.^[6][2][7]

Monoamine release of phenylpropylamine and related agents (EC₅₀Tooltip Half maximal effective concentration, nM)

Compound	NETooltip Norepinephrine	DATooltip Dopamine	5-HTTooltip Serotonin	Ref
Phenethylamine (2-phenylethylamine)	10.9	39.5	>10,000	[8][1][2]
Phenylpropylamine (3-phenylpropylamine)	222	1,491	ND	[1][2]
β-Methylphenethylamine (2-phenylpropylamine)	126	627	ND	[9]
Dextroamphetamine (d-phenylisopropylamine)	6.6–7.2	5.8–24.8	698–1,765	[10][11]
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:[12][6]

See also

• Homo-MDA
• Homo-MDMA