Chemistry:RU-27849

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RU-27849 is a serotonin receptor modulator. It can be regarded as a conformationally restricted tricyclic derivative of tryptamine or a structurally simplified derivative of LSD. This molecule was developed during structure–activity relationship (SAR) studies of LSD.[1][2][3][4]

It shows affinity for serotonin receptors, including for the serotonin 5-HT1, 5-HT1A, and 5-HT2 receptors (IC50 = 267–520 nM, 325–326 nM, and 1,964–2,900 nM, respectively).[1][2][5] 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 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][6] A number of other derivatives also exist, including FHATHBIN (6-hydroxy), 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][7][5][8]

RU-27849 was first described in the scientific literature by 1981.[3][1][2][5]

See also

  • Partial lysergamide
  • N-DEAOP-NMT
  • CT-5252
  • Paliclavine
  • 2C-B-5-hemiFLY-α6

References

  1. ↑ 1.0 1.1 1.2 1.3 "The Development of Indoleamine Derivatives Selective for Subtypes of Serotonin Receptors". The University of Arizona.. 1985. https://repository.arizona.edu/handle/10150/188104. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "Relative selectivity of some conformationally constrained tryptamine analogs at 5-HT1, 5-HT1A and 5-HT2 recognition sites". Life Sciences 41 (16): 1961–1969. October 1987. 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. ↑ 3.0 3.1 3.2 3.3 "Dopaminergic activity of some simplified ergoline derivatives". Drug Development Research 1 (2): 151–161. 1981. doi:10.1002/ddr.430010208. ISSN 0272-4391. 
  4. ↑ "Stereochemical Aspects of Hallucinogenesis". Biochemistry and Physiology of Substance Abuse. 3. Boca Raton, Fla.: CRC Press. 1991. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. https://bitnest.netfirms.com/external/Books/BiochemistryPhysiologySubstanceAbuse3.1. 
  5. ↑ 5.0 5.1 5.2 "Structure-activity relationships at 5-HT1A receptors: binding profiles and intrinsic activity". Pharmacology, Biochemistry, and Behavior 40 (4): 1041–1051. December 1991. doi:10.1016/0091-3057(91)90124-k. PMID 1816558. 
  6. ↑ "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. 1984. 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". 
  7. ↑ "Concepts for the design of 5-HT 1A serotonin agonists and antagonists". Drug Development Research 26 (3): 251–274. 1992. doi:10.1002/ddr.430260306. ISSN 0272-4391. 
  8. ↑ "6-substituted tricyclic partial ergoline compounds are selective and potent 5-hydroxytryptamine1A receptor agents". Life Sciences 47 (15): 1331–1337. 1990. doi:10.1016/0024-3205(90)90197-y. PMID 2172684. 



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