RU-27251

RU-27251, also known as 3,5-secoergoline or as 4-piperidin-3-yl-1H-indole, is a serotonin receptor modulator and dopamine receptor agonist of the partial ergoline family.^[1]^[2]^[3]^[4] Its affinity (K_D) for the dopamine D₂^high receptor was 72 nM and for the dopamine D₂^low receptor was 11,600 nM.^[3] RU-27251 was first described in the scientific literature by 1983.^[4]

Other namesRU27251; 3,5-Secoergoline

Drug classSerotonin receptor modulator; Dopamine receptor modulator; Partial ergoline

ATC code

None

CAS Number

81887-47-0
81887-48-1
16176-75-3

Quick facts Clinical data, Other names ...

RU-27251
Clinical data

Other names	RU27251; 3,5-Secoergoline
Drug class	Serotonin receptor modulator; Dopamine receptor modulator; Partial ergoline
ATC code	None
Identifiers
IUPAC name 4-piperidin-3-yl-1H-indole
CAS Number	81887-47-0 81887-48-1 16176-75-3
PubChem CID	3067718
ChemSpider	2327800
CompTox Dashboard (EPA)	DTXSID501002284
Chemical and physical data
Formula	C₁₃H₁₆N₂
Molar mass	200.285 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CC(CNC1)C2=C3C=CNC3=CC=C2
InChI InChI=1S/C13H16N2/c1-4-11(10-3-2-7-14-9-10)12-6-8-15-13(12)5-1/h1,4-6,8,10,14-15H,2-3,7,9H2 Key:JWMGZQMVMZBMFM-UHFFFAOYSA-N

References

[1]
Osman R, Mazurek AP, Weinstein H (1987). "Simulation of Molecular Stereoelectronic Mechanism for the Interaction of Hallucinogens and Indole Derivatives at 5-HT Receptors". Steric Aspects of Biomolecular Interactions. CRC Press. pp. 199–210. doi:10.1201/9781351076890-10. ISBN 978-1-351-07689-0. Retrieved 1 June 2025. An unexpected opportunity to test the theoretical hypothesis regarding the role of the electrostatic properties of the double bond region in determining a 5-HT-like recognition pattern of indole derivatives was offered by the publication of some novel LSD derivatives designed to investigate the actions of ergolines on dopamine receptors. 29 • 30 The generic structures of these 3,5 secoergolines are shown in Figure 3 (Roussel compounds) in comparison to those of other compounds known to act on 5-HT receptors. The group of Roussel compounds includes pairs in which one member retains the double bond while in the other the bond is saturated. The secoergolines were obtained from Roussel-UCLAF in France, their properties were calculated, and their affinities for 5-HT binding sites were determined by our colleagues. The results support our hypothesis that 5-HT-like recognition of LSD derivatives is based on the similarity in the reactivity properties conferred by the double bond region. As seen from the comparison of molecular electrostatic potentials of LSD, DiH-LSD, and the pair of Roussel analogs RU27510 and RU27251 (Figure 4), the properties of the pairs differ only in that region; compounds in which the crucial double bond is saturated lack one of the minima in the MEP. The pattern of the MEP map becomes more similar to that of tryptamine and SKF 1085618 than to that of 5-HT. 25 • 28 • 31 In agreement with the disappearance of the 5-HT-like recognition element, the ratio of IC50 values for binding to sites labeled by 3 H-5-HT was found to be near 20 for the LSD:Di-H-LSD pair and 80 for the RU27510:RU27251 pair (unpublished results). This ranking should be expected from our mechanistic hypothesis for recognition at 5-HT receptors.
[2]
Paulis TD (1983). "Chapter 3. Antipsychotic Agents and Dopamine Agonists". Annual Reports in Medicinal Chemistry. Vol. 18. Elsevier. pp. 21–30. doi:10.1016/s0065-7743(08)60758-7. ISBN 978-0-12-040518-3. Retrieved 1 June 2025. Replacement of the hydroxyl group with indole nitrogen (RU 27251, 41a) retains [dopamine] agonist activity.102 [...] 102. J.R. Boissier. L. Nedelec, C.O. Oberlander and F. Labrie, Proc.Symp.Dopamine Receptor Agonists (Stockholm, April 20-22, 1982). Acta Pharm.Suec.Suppl. 2, 120 (1983).
[3]
Seeman P, Watanabe M, Grigoriadis D, Tedesco JL, George SR, Svensson U, et al. (November 1985). "Dopamine D2 receptor binding sites for agonists. A tetrahedral model". Molecular Pharmacology. 28 (5): 391–399. doi:10.1016/S0026-895X(25)14176-X. PMID 2932631. TABLE 1 Binding of [3H]spiperone to D2 receptors [...]
[4]
Boissier JR, Nedelec L, Oberlander C, Labrie F (1983). "Simplified ergolines as new dopamine agonists". Acta Pharm. Suec. Supp. 2: 120–131.

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