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RU-27849

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RU-27849
Clinical data
Other namesRU27849; 4-Amino-1,3,4,5-tetrahydrobenz[c,d]indole
Drug classSerotonin receptor modulators
Identifiers
  • 1,3,4,5-tetrahydrobenzo[c,d]indol-4-amine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC11H12N2
Molar mass172.231 g·mol−1
3D model (JSmol)
  • C1C(CC2=CNC3=CC=CC1=C23)N
  • InChI=1S/C11H12N2/c12-9-4-7-2-1-3-10-11(7)8(5-9)6-13-10/h1-3,6,9,13H,4-5,12H2
  • Key:JPTWSZJFCLJZJX-UHFFFAOYSA-N

RU-27849 is a serotonin receptor modulator and is described as a "simplified" or "partial ergoline" and "conformationally constrained" or "rigid tryptamine" which was developed during structure–activity relationship (SAR) studies of these structural families.[1][2][3]

It shows affinity for serotonin receptors, including for the serotonin 5-HT1, 5-HT1A, and 5-HT2 receptors (IC50Tooltip half-maximal inhibitory concentration = 267–520 nM, 325–326 nM, and 1,964–2,900 nM, respectively).[1][2][4] RU-27849's affinities for serotonin receptors are similar to but lower than those of tryptamine and dimethyltryptamine (DMT).[1][2] It shows very weak affinity for dopamine receptors and weak associated associated activity.[3]

The 6-methoxy derivative of RU-27849, which is to RU-27849 as 5-methoxytryptamine is to tryptamine, appears to have much higher affinity for serotonin receptors than RU-27849 itself (IC50 ≈ 50 nM).[2][5] A number of other derivatives also exist, including RU-28306 (N,N-dimethyl), RU-28251 (N,N-dipropyl), Bay R 1531 (LY-197206; 6-methoxy-N,N-dipropyl), LY-293284 ((4R)-6-acetyl-N,N-dipropyl), and LY-178210 (6-carboxamido-N,N-dipropyl), as well as NDTDI, among others.[3][6][4][7]

RU-27849 was first described in the scientific literature by 1981.[3][1][2][4]

References

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  1. ^ a b c d Taylor, Ethan Will. (1985). "The Development of Indoleamine Derivatives Selective for Subtypes of Serotonin Receptors". The University of Arizona. Retrieved 18 March 2025.
  2. ^ a b c d e Taylor EW, Nikam S, Weck B, Martin A, Nelson D (October 1987). "Relative selectivity of some conformationally constrained tryptamine analogs at 5-HT1, 5-HT1A and 5-HT2 recognition sites". Life Sci. 41 (16): 1961–1969. doi:10.1016/0024-3205(87)90749-1. PMID 3657392. The observation that the partial ergolines do not show significantly enhanced potency at any of the 5-HT recognition sites is somewhat unexpected, considering the high affinity shown by full ergoline derivatives such as d-LSD and metergoline for those sites. Consistent results have been reported for the methoxy derivative of RU 27849, which was recently synthesised (23) and reported to have an IC50 of about 50 nM for the inhibition of [3H]5-HT binding, which is at least 5 times less potent than typical reported values for the corresponding non-rigid analog, 5-MeO-TRYP.
  3. ^ a b c d Euvrard, Catherine; Ferland, Louise; Fortin, Michel; Oberlander, Claude; Labrie, Fernand; Boissier, Jacques R. (1981). "Dopaminergic activity of some simplified ergoline derivatives". Drug Development Research. 1 (2): 151–161. doi:10.1002/ddr.430010208. ISSN 0272-4391.
  4. ^ a b c Nelson DL (December 1991). "Structure-activity relationships at 5-HT1A receptors: binding profiles and intrinsic activity". Pharmacol Biochem Behav. 40 (4): 1041–1051. doi:10.1016/0091-3057(91)90124-k. PMID 1816558.
  5. ^ Kruse, Lawrence I.; Meyer, Michael D. (1984). "Ergoline synthons. 2. Synthesis of 1,5-dihydrobenz[cd]indol-4(3H)-ones and 1,3,4,5-tetrahydrobenz[cd]indol-4-amines". The Journal of Organic Chemistry. 49 (25): 4761–4768. doi:10.1021/jo00199a004. ISSN 0022-3263. Lastly, in the context of our original goal of producing a rigid serotonin congener of optimum side-chain conformation, it is interesting to note that 2b (R2 = H2) displaces 3[H]-5-HT from rat frontal cortex with an IC50 of ~50 nM.36
  6. ^ Glennon, Richard A. (1992). "Concepts for the design of 5‐HT 1A serotonin agonists and antagonists". Drug Development Research. 26 (3): 251–274. doi:10.1002/ddr.430260306. ISSN 0272-4391.
  7. ^ Slaughter JL, Harrington MA, Peroutka SJ (1990). "6-substituted tricyclic partial ergoline compounds are selective and potent 5-hydroxytryptamine1A receptor agents". Life Sci. 47 (15): 1331–1337. doi:10.1016/0024-3205(90)90197-y. PMID 2172684.
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