LR-1111

Last updated

LR-1111
LR-1111.svg
Clinical data
Other namesLR 1111
Identifiers
  • 1-(2-benzhydryloxyethyl)-4-(3-phenylpropyl)-1,4-diazepane
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C29H36N2O
Molar mass 428.620 g·mol−1
3D model (JSmol)
  • C1CN(CCN(C1)CCOC(C2=CC=CC=C2)C3=CC=CC=C3)CCCC4=CC=CC=C4
  • InChI=1S/C29H36N2O/c1-4-12-26(13-5-1)14-10-19-30-20-11-21-31(23-22-30)24-25-32-29(27-15-6-2-7-16-27)28-17-8-3-9-18-28/h1-9,12-13,15-18,29H,10-11,14,19-25H2
  • Key:IRSSQYPVPPWBSQ-UHFFFAOYSA-N

LR-1111 is an analog of GBR-12935 that was discovered by Richard Rothman and co-workers in the 1990's. It differs from GBR-12935 in that the piperazine has been expanded to a homopiperazine (azepane) ring. [1] LR-1111 is a dopamine reuptake inhibitor (DRI) with over 4000 times selectivity for the dopamine transporter (DAT) relative to the serotonin transporter (SERT) and the norepinephrine transporter (NET). [2] [3]

Contents

See also

References

  1. ↑ Matecka D, Rothman RB, Radesca L, Costa BR, Dersch CM, Partilla JS, et al. (1 January 1996). "Development of Novel, Potent, and Selective Dopamine Reuptake Inhibitors through Alteration of the Piperazine Ring of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909)". Journal of Medicinal Chemistry. 39 (24): 4704–4716. doi:10.1021/jm960305h. PMID   8941383.
  2. ↑ Rothman RB, Lewis B, Dersch C, Xu H, Radesca L, Costa BR, et al. (May 1993). "Identification of a GBR12935 homolog, LR1111, which is over 4,000-fold selective for the dopamine transporter, relative to serotonin and norepinephrine transporters". Synapse. 14 (1). New York, N.Y.: 34–39. doi:10.1002/syn.890140106. PMID   8511716.
  3. ↑ Silverthorn ML, Dersch CM, Baumann MH, Cadet JL, Partilla JS, Rice KC, et al. (Apr 1995). "Studies of the biogenic amine transporters. V. Demonstration of two binding sites for the cocaine analog [125I]RTI-55 associated with the 5-HT transporter in rat brain membranes". The Journal of Pharmacology and Experimental Therapeutics. 273 (1): 213–222. doi:10.1016/S0022-3565(25)09513-8. PMID   7714769.
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