N-(2-cyanoethyl)phenethylamine

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CEPEA
Clinical data
Other namesN-Cyanoethylphenethylamine; CEPEA; CE-PEA; α-Desmethylfenproporex; α-Desmethyl-fenproporex; PEA-P
Drug classMonoamine releasing agent; Stimulant
ATC code
  • None
Identifiers
  • 3-(2-phenylethylamino)propanenitrile
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)CCNCCC#N
  • InChI=1S/C11H14N2/c12-8-4-9-13-10-7-11-5-2-1-3-6-11/h1-3,5-6,13H,4,7,9-10H2
  • Key:LVHAIJJWSYXSLW-UHFFFAOYSA-N

N-(2-Cyanoethyl)phenethylamine (CEPEA) is a stimulant drug of the phenethylamine family related to phenethylamine (PEA).[1][2][3] It is the N-(2-cyanoethyl) derivative of phenethylamine.[1][2][3]

The drug acts as a prodrug of phenethylamine and hence is a monoamine releasing agent similarly.[1][2][3] It shows greatly sustained phenethylamine levels and neurochemical effects in rodents compared to phenethylamine itself however.[1][2][3] As an example, the elimination half-life of phenethylamine was 1.1 minutes whereas the half-life of CEPEA was 27 minutes.[2] Total exposure to phenethylamine with CEPEA in blood and brain was no greater than with phenethylamine itself in rodents, but exposure to phenethylamine with CEPEA was much greater in the liver than with phenethylamine itself.[2]

The chemical synthesis of CEPEA has been described.[2] Analogues of CEPEA include fenproporex (α-methyl-CEPEA or N-(2-cyanoethyl)amphetamine)[4] and N-(2-cyanoethyl)tranylcypromine (CE-TCP).[2][5][6] Another notable analogue of CEPEA is N-(ethoxycarbonyl)phenethylamine (CAR-PEA), which is a prodrug of phenethylamine similarly to CEPEA.[1][7] Other phenethylamine prodrugs have been described as well.[3]

CEPEA was first described in the scientific literature by 1985.[1][2][3]

See also

References

  1. Coutts RT, Baker GB, Nazarali AJ, Rao TS, Micetich RG, Hall TW (1985). "Prodrugs of Trace Amines". Neuropsychopharmacology of the Trace Amines. Totowa, NJ: Humana Press. pp. 175–180. doi:10.1007/978-1-4612-5010-4_15. ISBN 978-1-4612-9397-2.
  2. Baker GB, Coutts RT, Rao TS (October 1987). "Neuropharmacological and neurochemical properties of N-(2-cyanoethyl)-2-phenylethylamine, a prodrug of 2-phenylethylamine". British Journal of Pharmacology. 92 (2): 243–255. doi:10.1111/j.1476-5381.1987.tb11318.x. PMC 1853650. PMID 2890391.
  3. Baker GB, Coutts RT, Rao TS, Hall TW, Micetich RG (1988). "Prodrugs of β-Phenylethylamine and Tryptamine: Studies in the Rat". Trace Amines. Totowa, NJ: Humana Press. pp. 321–334. doi:10.1007/978-1-4612-4602-2_30. ISBN 978-1-4612-8945-6.
  4. Coutts RT, Nazarali AJ, Baker GB, Pasutto FM (June 1986). "Metabolism and disposition of N-(2-cyanoethyl)amphetamine (fenproporex) and amphetamine: study in the rat brain". Canadian Journal of Physiology and Pharmacology. 64 (6): 724–728. doi:10.1139/y86-122. PMID 3756624.
  5. Nazarali AJ, Baker GB, Coutts RT, Wong TF (February 1987). "N-(2-cyanoethyl)tranylcypromine, a potential prodrug of tranylcypromine: its disposition and interaction with catecholamine neurotransmitters in brain". Pharmaceutical Research. 4 (1): 16–20. doi:10.1023/a:1016417624741. PMID 3508523.
  6. Nazarali AJ, Baker GB, Coutts RT, Greenshaw AJ (1987). "Para-hydroxytranylcypromine: presence in rat brain and heart following administration of tranylcypromine and an N-cyanoethyl analogue". European Journal of Drug Metabolism and Pharmacokinetics. 12 (3): 207–214. doi:10.1007/BF03189899. PMID 3436344.
  7. Baker GB, Coutts RT, Nazarali AJ, Danielson TJ, Rubens M (1984). "Carbamate prodrugs of phenylethylamines: a neurochemical investigation". Proceedings of the Western Pharmacology Society. 27: 523–525. PMID 6494193.