13-Hydroxylergotrile

vanc 6 13-Hydroxylergotrile structure.svg skin-invert-image 175px Dopamine receptor agonist None 2-Chloro-6-methyl-13-hydroxyergoline-8β-acetonitrile 17 17 1 3 1 ClC1=C2C3C(=CC(O[H])=CC=3[C@]([H])3C[C@@](CC#N)CN(C)[C@]3([H])C2)N1[H] 1S/C17H17ClN3O/c1-21-8-9(2-3-19)4-11-12-5-10(22)6-14-16(12)13(7-15(11)21)17(18)20-14/h5-6,11,15,20,22H,2,4,7-8H2,1H3/t11-,15-/m1/s1 KFEUDMMGAVSBGW-IAQYHMDHSA-N 13-Hydroxylergotrile, also known as 2-chloro-6-methyl-13-hydroxyergoline-8β-acetonitrile, is a dopamine receptor agonist of the ergoline family. Parli CJ, Schmidt B, Shaar CJ Metabolism of lergotrile to 13-hydroxy lergotrile, a potent inhibitor of prolactin release in vitro Biochemical Pharmacology 27 9 1405–1408 May 1978 29651 10.1016/0006-2952(78)90131-4 Cannon JG, Lee T, Ilhan M, Koons J, Long JP 6-Hydroxy-4-[2-(di-n-propylamino)ethyl]indole: synthesis and dopaminergic actions Journal of Medicinal Chemistry 27 3 386–389 March 1984 6699883 10.1021/jm00369a026 Prior communications have described prominent dopaminergic agonist actions of a simple indole derivative, 1, designed as a fragment of the dopaminergic ergoline derivative lergotrile (2). The slow (30–40 min) onset of pharmacological effects following intravenous administration of 1 in intact animals, coupled with its dopaminergic inactivity in an in vitro assay using isolated cat atrium and its very weak binding activity in calf caudate tissue,2 led to the proposal that 1 may be metabolically activated in vivo. Wong and Bymaster4 reported that 13-hydroxylergotrile (3)) a metabolite of lergotrile, had greater affinity than lergotrile in a dopamine agonist receptor binding assay. Parli et al.5 reported that 13-hydroxylergotrile is 100 times more active than lergotrile in vitro in inhibiting prolactin release from the anterior pituitary. It is an active metabolite of the never-marketed antiparkinsonian agent lergotrile (LY-79907). The drug has been found to be 100-fold more potent as a dopamine receptor agonist than lergotrile itself in vitro. 13-Hydroxylergotrile was first described in the scientific literature by 1978. See also Substituted ergoline 13-Hydroxy-LSD References Category:Chloroarenes Category:Dopamine agonists Category:Ergolines Category:Human drug metabolites Category:Hydroxyarenes Category:Nitriles Category:Prolactin inhibitors