Lergotrile

Lergotrile

Clinical data
Other names	LY-79907; 2-Chloro-6-methylergoline-8β-acetonitrile
Identifiers
IUPAC name 2-[(6aR,9S,10aR)-5-chloro-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]acetonitrile
CAS Number	36945-03-6  Y
PubChem CID	6918447
ChemSpider	5293644
UNII	O68JXU1W09
KEGG	D04693
ChEMBL	ChEMBL80937
CompTox Dashboard (EPA)	DTXSID701043282
Chemical and physical data
Formula	C17H18ClN3
Molar mass	299.80 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1C[C@@H](C[C@H]2[C@H]1CC3=C(NC4=CC=CC2=C34)Cl)CC#N
InChI InChI=1S/C17H18ClN3/c1-21-9-10(5-6-19)7-12-11-3-2-4-14-16(11)13(8-15(12)21)17(18)20-14/h2-4,10,12,15,20H,5,7-9H2,1H3/t10-,12-,15-/m1/s1 Key:JKAHWGPTNVUTNB-IXPVHAAZSA-N

Lergotrile (INN Tooltip International Nonproprietary Name, USAN Tooltip United States Adopted Name; developmental code name LY-79907) is an ergoline derivative which acts as a dopamine receptor agonist. It was developed for the treatment of Parkinson's disease, but failed in clinical trials due to liver toxicity. ^{[1] [2]}

The drug's hydroxylated metabolite 13-hydroxylergotrile is 100-fold more potent as a dopamine receptor agonist than lergotrile itself in vitro . ^{[3] [4]}

See also

• Substituted ergoline

References

1. Lieberman AN, Gopinathan G, Estey E, Kupersmith M, Goodgold A, Goldstein M (February 1979). "Lergotrile in Parkinson disease: further studies". Neurology. 29 (2): 267–72. doi:10.1212/wnl.29.2.267. PMID   34808.
2. Cunningham KA, Callahan PM, Appel JB (July 1984). "Discriminative stimulus properties of lergotrile". The Journal of Pharmacology and Experimental Therapeutics. 230 (1): 47–52. PMID   6146709.
3. Nichols DE (April 2016). Barker EL (ed.). "Psychedelics". Pharmacological Reviews. 68 (2): 264–355. doi:10.1124/pr.115.011478. ISSN   0031-6997. PMC   4813425 . PMID   26841800.
4. Parli CJ, Schmidt B, Shaar CJ (May 1978). "Metabolism of lergotrile to 13-hydroxy lergotrile, a potent inhibitor of prolactin release in vitro". Biochemical Pharmacology. 27 (9): 1405–1408. doi:10.1016/0006-2952(78)90131-4. PMID   29651.