6-Ethyl-9-oxaergoline

6-Ethyl-9-oxaergoline
Clinical data
Other namesEOE; 6-EOE; N-Ethyl-9-oxaergoline
Drug classDopamine receptor agonist; Adrenergic receptor modulator; Serotonin receptor modulator
ATC code
  • None
Identifiers
  • (7R)-6-ethyl-3-oxa-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H18N2O
Molar mass242.322 g·mol−1
3D model (JSmol)
  • CCN1CCOC2[C@H]1CC3=CNC4=CC=CC2=C34
  • InChI=1S/C15H18N2O/c1-2-17-6-7-18-15-11-4-3-5-12-14(11)10(9-16-12)8-13(15)17/h3-5,9,13,15-16H,2,6-8H2,1H3/t13-,15?/m1/s1
  • Key:ILMWHLYQRWFIJV-AFYYWNPRSA-N

6-Ethyl-9-oxaergoline (EOE), also known as N-ethyl-9-oxaergoline, is a dopamine receptor agonist of the 9-oxaergoline family.[1][2] It is a potent dopamine receptor agonist and produces effects in animals including antiparkinsonian-like effects, stereotypy, hypothermia, hypolocomotion at lower doses and hyperlocomotion at higher doses, and emesis.[1] In addition to its dopaminergic activity, EOE shows agonist and antagonist activities at the α2-adrenergic receptor.[3][2] It shows weaker affinity for the serotonin 5-HT1 and 5-HT2 receptors as well.[2][4] EOE was first described in the scientific literature in 1982.[5][1][3][2]

See also

References

  1. 1 2 3 Martin GE, Williams M, Clineschmidt BV, Yarbrough GG, Jones JH, Haubrich DR (May 1982). "Potent dopamine agonist activity of a novel ergoline, 6-ethyl-9-oxaergoline (EOE)". Life Sciences. 30 (21): 1847–1856. doi:10.1016/0024-3205(82)90323-x. PMID 7201555.
  2. 1 2 3 4 Williams M, Jones JH, Watling KJ (1983). "Biochemical characterization of the enantiomers of the novel ergoline dopamine agonist 6-ethyl-9-oxaergoline (EOE)". Drug Development Research. 3 (6): 573–579. doi:10.1002/ddr.430030610. ISSN 0272-4391.
  3. 1 2 Lotti VJ, Taylor DA (November 1982). "alpha 2-Adrenergic agonist and antagonist activity of the respective (-)-and (+)-enantiomers of 6-ethyl-9-oxaergoline (EOE)". European Journal of Pharmacology. 85 (2): 211–215. doi:10.1016/0014-2999(82)90468-x. PMID 6129984.
  4. ↑ Martin GE, Williams M, Pettibone DJ, Zrada MM, Lotti VJ, Taylor DA, et al. (May 1985). "Selectivity of (+)-4-propyl-9-hydroxynaphthoxazine [(+)-PHNO] for dopamine receptors in vitro and in vivo". The Journal of Pharmacology and Experimental Therapeutics. 233 (2): 395–401. doi:10.1016/S0022-3565(25)21227-7. PMID 2987478.
  5. ↑ Anderson PS, Baldwin JJ, McClure DE, Lundell GF, Jones JH (1982). "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. doi:10.1021/jo00132a040. ISSN 0022-3263.
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