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Compound

Phenylpropylamine

Also called 3-Phenylpropylamine, 3-phenylpropan-1-amine, Benzenepropanamine

Original Wikipedia articleen.wikipedia.org/wiki/Phenylpropylamine revision used (24 October 2026)

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Overview

Phenylpropylamine, also known as 3-phenylpropylamine, is a monoamine releasing agent (MRA) related to phenethylamine (2-phenylethylamine). 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] WP

Phenylpropylamine was synthesized and characterized during investigations of the structure–activity relationships (SAR) of phenethylamine and amphetamine MRAs. It acts as a norepinephrine–dopamine releasing agent (NDRA). 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] WP

The analogue of phenethylamine with the ethylamine side chain shortened by one carbon atom to instead be a methylamine chain is benzylamine (phenylmethylamine). In contrast to phenethylamine and phenylpropylamine, benzylamine is said to be inactive as a norepinephrine releasing agent (NRA). However, certain derivatives of benzylamine have nonetheless been found to show MRA-like effects in animals. In addition, benzylpiperazine, an analogue of benzylamine with a methylamine-like side chain, is a potent MRA and psychostimulant.[2–7] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.

Chemistry

Formula
C9H13N PC
CAS number
2038-57-5 PC
Molar mass (g/mol)
135.21 PC
IUPAC name (computed by PubChem)
3-phenylpropan-1-amine PC
SMILES
C1=CC=C(C=C1)CCCN PC
InChIKey
LYUQWQRTDLVQGA-UHFFFAOYSA-N PC
PubChem CID
16259

Harm reduction information

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Sources

  1. Other Forsyth AN. Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines. 22 May 2012
  2. Other Blough B. Dopamine Transporters: Chemistry, Biology and Pharmacology. July 2008
  3. Journal / agency Biel JH, Bopp BA. Stimulants. 1978. doi:10.1007/978-1-4757-0510-2_1
  4. Other Shulgin A, Manning T, Daley PF. The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 2011
  5. Journal / agency Bronson ME, Barrios-Zambrano L, Jiang W, Clark CR, DeRuiter J, Newland MC. Behavioral and developmental effects of two 3,4-methylenedioxymethamphetamine (MDMA) derivatives. Drug Alcohol Depend. December 1994. doi:10.1016/0376-8716(94)90141-4 · PMID 7889806
  6. Journal / agency Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Current Topics in Medicinal Chemistry. 2006. doi:10.2174/156802606778249766 · PMID 17017961
  7. Journal / agency Gee P, Schep LJ. Novel Psychoactive Substances. 2022. doi:10.1016/b978-0-12-818788-3.00009-7

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.