Chemistry:9-Oxaergoline

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9-Oxaergoline is a low-potency dopamine receptor agonist related to the ergolines.[1][2][3] It is the analogue and bioisostere of ergoline in which the carbon atom at the 9 position of the ergoline ring system has been replaced with an oxygen atom.[1][2][3] A few notable derivatives of 9-oxaergoline have been studied and characterized, including RU-29717 (N-propyl-9-oxaergoline), 6-ethyl-9-oxaergoline (EOE), and voxergolide (RU-41656), which are all substantially more potent as dopamine receptor agonists than 9-oxaergoline itself.[3][4] Other derivatives, such as N-methyl-9-oxaergoline, have been characterized as well.[3] In addition to its dopaminergic activity, RU-29717 is notable in also having affinity for serotonin receptors and in producing a short-lasting head-twitch response in rodents.[5][6] The head-twitch response is notable in being a behavioral proxy of psychedelic effects caused by serotonin 5-HT2A receptor agonism.[7][8] The potential serotonergic activities of 9-oxaergoline and N-methyl-9-oxaergoline do not appear to have been reported.[1][2][3][5][6]

See also

References

  1. ↑ 1.0 1.1 1.2 "A new class of D-heteroergolines: total synthesis and resolution of a 9-oxaergoline, 4,6,6a,8,9,10a-hexahydro-7-ethyl-7H-indolo[3,4-gh][1,4]benzoxazine". The Journal of Organic Chemistry 47 (11): 2184–2187. 1982. doi:10.1021/jo00132a040. ISSN 0022-3263. 
  2. ↑ 2.0 2.1 2.2 "Synthesis of (7R)-7H-indolo[3,4-gh][1,4]benzoxazines, a new class of D-heteroergolines with dopamine agonist activity". Journal of Medicinal Chemistry 26 (3): 363–367. March 1983. doi:10.1021/jm00357a010. PMID 6298427. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Synthesis and central dopaminergic activities of (+/-)-hexahydro-7H-indolo[3,4-gh][1,4]benzoxazine derivatives [(+/-)-9-oxaergolines]". Journal of Medicinal Chemistry 26 (4): 522–527. April 1983. doi:10.1021/jm00358a012. PMID 6834383. 
  4. ↑ "The Roman strains of rats as a psychogenetic tool for pharmacological investigation of working memory: example with RU 41656". Psychopharmacology 107 (2–3): 415–424. 1992. doi:10.1007/BF02245169. PMID 1352059. 
  5. ↑ 5.0 5.1 "Comparative study of central dopaminergic properties of RU 29717 (N-propyl-9-oxaergoline) and pergolide". European Journal of Pharmacology 87 (2–3): 183–189. February 1983. doi:10.1016/0014-2999(83)90328-x. PMID 6857756. "The relatively low affinity of pergolide for 5-HT receptors compared to that of RU 29717 is in keeping with the lack of biochemical evidence of altered 5-HT function (Fuller et al., 1979). It has been observed that RU 29717 induced short-lasting head-twitches in mice (results not shown). This result, favouring a 5-HT agonist property could be of value for its potential therapeutic interest (Silbergeld and Hruska, 1979).". 
  6. ↑ 6.0 6.1 "Neuropharmacological profile of a new series of dopamine agonists: N-n-propyl-hexahydronaphthoxazines". European Journal of Pharmacology 124 (1–2): 93–106. May 1986. doi:10.1016/0014-2999(86)90128-7. PMID 3720849. 
  7. ↑ "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. 36. 2018. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. 
  8. ↑ "Preclinical models for evaluating psychedelics in the treatment of major depressive disorder". British Journal of Pharmacology. October 2024. doi:10.1111/bph.17370. PMID 39467003. 



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