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RU-28251

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Pharmaceutical compound
RU-28251
Clinical data
Other namesRU28251; 4,α-Methylene-N,N-dipropyltryptamine; 4,α-Methylene-DPT
Drug class Dopamine receptor agonist; D2-like receptor agonist; Serotonin receptor modulator; Prolactin inhibitor
ATC code
  • None
Identifiers
  • N,N-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C17H24N2
Molar mass 256.393g·mol−1
3D model (JSmol)
  • CCCN(CCC)C1CC2=C3C(=CNC3=CC=C2)C1
  • InChI=1S/C17H24N2/c1-3-8-19(9-4-2)15-10-13-6-5-7-16-17(13)14(11-15)12-18-16/h5-7,12,15,18H,3-4,8-11H2,1-2H3
  • Key:YBHBWJNGSCDSMJ-UHFFFAOYSA-N

RU-28251, also known as 4,α-methylene-N,N-dipropyltryptamine (4,α-methylene-DPT), is a tricyclic cyclized tryptamine and simplified or partial ergoline.[1] [2] [3] [4] [5] [6] It is a dopamine D2-like receptor agonist [5] and shows affinity for the serotonin 5-HT1 and 5-HT2 receptors (IC50 Tooltip half-maximal inhibitory concentration = 141nM and 723nM, respectively).[1] The drug inhibits prolactin secretion in animals.[5] The chemical synthesis of RU-28251 has been described.[1] RU-28251 was first described in the scientific literature by 1978.[3] [7]

See also

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References

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  1. 1 2 3 Flaugh ME, Mullen DL, Fuller RW, Mason NR. "6-substituted 1,3,4,5-tetrahydrobenz[cd]indol-4-amines: potent serotonin agonists". J Med Chem. doi:10.1021/jm00117a013. PMID 2457705.
  2. ↑ Kaiser C (1984). "Structure—Activity Relationships of Dopamine Receptor Agonists". Dopamine Receptor Agonists. Boston, MA: Springer US. pp. 87–137. doi:10.1007/978-1-4757-0310-8_4. ISBN 978-1-4757-0312-2 . Retrieved 1 June 2025. Some simpler derivatives of the ergot-type compounds also demonstrate significant DA-like activity. Such compounds include the ergoline fragment 25 (RU 28251) (Euvrard et al., 1981), which has been claimed (Bach and Kornfeld, 1978) to have OA-like properties, e.g., inhibition of prolactin secretion and displacement of OA from binding sites.
  3. 1 2 Bach NJ, Kornfeld EC, Jones ND, Chaney MO, Dorman DE, Paschal JW, et al. (May 1980). "Bicyclic and tricyclic ergoline partial structures. Rigid 3-(2-aminoethyl)pyrroles and 3- and 4-(2-aminoethyl)pyrazoles as dopamine agonists". Journal of Medicinal Chemistry. 23 (5): 481–491. doi:10.1021/jm00179a003. PMID 7189782.
  4. ↑ Euvrard C, Ferland L, Fortin M, Oberlander C, Labrie F, Boissier JR (1981). "Dopaminergic activity of some simplified ergoline derivatives". Drug Development Research. 1 (2): 151–161. doi:10.1002/ddr.430010208. ISSN 0272-4391.
  5. 1 2 3 Goldman ME, Kebabian JW (1987). "Pharmacological Validation of the Two-Dopamine-Receptor Hypothesis". Clinical Pharmacology in Psychiatry. Vol. 3. pp. 201–213. doi:10.1007/978-3-642-71288-3_24. ISBN 978-3-642-71290-6. PMID 2950520. Table 1. Selective ligands of each dopamine receptor [...] D-2 [...] RU-28251 [...] 3.3.3 RU-28251 RU-28251, a partial ergoline containing a tricyclic ergoline ring (Fig. 5), was both a potent inhibitor of [3H]spiroperidol binding and an inhibitor of prolactin secretion (Bach et al. 1980; Euvrard et al. 1981). In addition, this agent caused contralateral rotation in lesioned rats (Bach et al. 1980). RU-28251, however, did not alter striatal adenylate cyclase activity (Euvrard et al. 1981). As with the other D-2 agonists, replacement of the n-propyl with a methyl or hydrogen resulted in decreased agonist activity. {{cite book}}: |journal= ignored (help)
  6. ↑ 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. Another ergoline analogue, RU 28251 (44), is a potent agonist in the Ungerstedt rotation model.102
  7. ↑ U.S. 4,110,339, Bach NJ, Kornfeld EC, "4-(Di-n-propyl)amino-1,3,4,5-tetrahydrobenz[cd]indole", issued 29 August 1978, assigned to Eli Lilly and Co.


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