RU-24213

RU-24213, also known as 3-hydroxy-N-propyl-N-(phenylethyl)phenethylamine, is a dopamine receptor agonist of the phenethylamine family related to dopamine.^[1]^[2]^[3] It is a selective dopamine D₂-like receptor agonist.^[1]^[3] Subsequently, however, RU-24213 was found to also act as a potent κ-opioid receptor (KOR) antagonist.^[2]^[4] It led to the development of the diphenylethylamine series of KOR ligands.^[4]^[5] RU-24213 was first described in the scientific literature in 1978.^[4]^[6]

Other namesRU24213; 3-Hydroxy-N-propyl-N-(phenylethyl)phenethylamine

Drug classDopamine receptor agonist; Dopamine D₂-like receptor agonist; κ-Opioid receptor antagonist

ATC code

None

PubChem CID

114876

Quick facts Clinical data, Other names ...

RU-24213
Clinical data

Other names	RU24213; 3-Hydroxy-N-propyl-N-(phenylethyl)phenethylamine
Drug class	Dopamine receptor agonist; Dopamine D₂-like receptor agonist; κ-Opioid receptor antagonist
ATC code	None
Identifiers
IUPAC name 3-[2-[2-phenylethyl(propyl)amino]ethyl]phenol
PubChem CID	114876
ChemSpider	102832
ChEMBL	ChEMBL1188090
Chemical and physical data
Formula	C₁₉H₂₅NO
Molar mass	283.415 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCN(CCC1=CC=CC=C1)CCC2=CC(=CC=C2)O
InChI InChI=1S/C19H25NO/c1-2-13-20(14-11-17-7-4-3-5-8-17)15-12-18-9-6-10-19(21)16-18/h3-10,16,21H,2,11-15H2,1H3 Key:QUZUPTMNMJTYGL-UHFFFAOYSA-N

References

[1]
Daly SA, Waddington JL (March 1992). "New classes of selective D-1 dopamine receptor antagonist provide further evidence for two directions of D-1:D-2 interaction". Neurochemistry International. 20 Suppl: 135S–139S. doi:10.1016/0197-0186(92)90226-h. PMID 1365412.
[2]
Fortin M, Degryse M, Petit F, Hunt PF (April 1991). "The dopamine D2 agonists RU 24213 and RU 24926 are also kappa-opioid receptor antagonists". Neuropharmacology. 30 (4): 409–412. doi:10.1016/0028-3908(91)90068-m. PMID 1677169.
[3]
Stoof JC, Kebabian JW (December 1984). "Two dopamine receptors: biochemistry, physiology and pharmacology". Life Sciences. 35 (23): 2281–2296. doi:10.1016/0024-3205(84)90519-8. PMID 6390056.
[4]
Spetea M, Schmidhammer H (2022). "Kappa Opioid Receptor Ligands and Pharmacology: Diphenethylamines, a Class of Structurally Distinct, Selective Kappa Opioid Ligands". Handbook of Experimental Pharmacology. Vol. 271. pp. 163–195. doi:10.1007/164_2020_431. ISBN 978-3-030-89073-5. PMID 33454858. The synthesis of the first diphenethylamine derivative, RU 24213 (1) (Fig. 10), was reported in 1978, originally developed as a potential anti-Parkinson's drug (Nedelec et al. 1978). RU 24213 (1) was described as a selective dopamine D2 receptor agonist (Euvrard et al. 1980), also found to bind with moderate affinity and selectivity to KOR and to have a KOR antagonist activity in vitro (Fortin et al. 1991). [...] These simple structures were used as leads for the design of small molecules targeting the KOR and featuring a diphenethylamine scaffold. [...]
[5]
Spetea M, Berzetei-Gurske IP, Guerrieri E, Schmidhammer H (November 2012). "Discovery and pharmacological evaluation of a diphenethylamine derivative (HS665), a highly potent and selective κ opioid receptor agonist". Journal of Medicinal Chemistry. 55 (22): 10302–10306. doi:10.1021/jm301258w. PMID 23134120.
[6]
Nedelec L, Dumont C, Oberlander C, Frechet D, Laurent J (1978). "Synthèse et étude de l'activité dopaminergique de dérivés de la di (phénéthyl) amine". European Journal of Medicinal Chemistry. 13 (6): 553–563. Retrieved 31 January 2026 – via Pascal and Francis Bibliographic Databases.

See also

References

External links

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