Dataset Information

Cis-1-Benzyl-pyrrolidine-2,5-dicarbonitrile.

ABSTRACT: In the title compound, C(13)H(13)N(3), the cyano groups at the 2- and 5-positions are eclipsed with each other. The phenyl ring is disordered over two sets of sites, with refined occupancies of 0.520?(5) and 0.480?(5). The angles between the mean plane of the pyrrolidine ring and the two cyano groups are 71.7?(9) and 75.0?(12)°.

SUBMITTER: Ponugoti PR

PROVIDER: S-EPMC3099760 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

cis-1-Benzyl-pyrrolidine-2,5-dicarbonitrile.

Ponugoti Purushothama Rao PR Penthala Narsimha Reddy NR Dwoskin Linda P LP Parkin Sean S Crooks Peter A PA

Acta crystallographica. Section E, Structure reports online 20110302 Pt 4

In the title compound, C(13)H(13)N(3), the cyano groups at the 2- and 5-positions are eclipsed with each other. The phenyl ring is disordered over two sets of sites, with refined occupancies of 0.520 (5) and 0.480 (5). The angles between the mean plane of the pyrrolidine ring and the two cyano groups are 71.7 (9) and 75.0 (12)°. ...[more]

PMID: 21754044

Similar Datasets

Project description:Both lobeline and lobelane attenuate methamphetamine self-administration in rats by decreasing methamphetamine-induced dopamine release via interaction with vesicular monoamine transporter-2 (VMAT2). A novel derivative of nor-lobelane, cis-2,5-di-(2-phenethyl)-pyrrolidine hydrochloride (UKCP-110), and its trans-isomers, (2R,5R)-trans-di-(2-phenethyl)-pyrrolidine hydrochloride (UKCP-111) and (2S,5S)-trans-di-(2-phenethyl)-pyrrolidine hydrochloride (UKCP-112), were evaluated for inhibition of [(3)H]dihydrotetrabenazine binding and [(3)H]dopamine uptake by using a rat synaptic vesicle preparation to assess VMAT2 interaction. Compounds were evaluated for inhibition of [(3)H]nicotine and [(3)H]methyllycaconitine binding to assess interaction with the major nicotinic receptor subtypes. In addition, compounds were evaluated for inhibition of methamphetamine-evoked endogenous dopamine release by using striatal slices. The most promising compound, UKCP-110, was evaluated for its ability to decrease methamphetamine self-administration and methamphetamine discriminative stimulus cues and for its effect on food-maintained operant responding. UKCP-110, UKCP-111, and UKCP-112 inhibited [(3)H]dihydrotetrabenazine binding (K(i) = 2.66 ± 0.37, 1.05 ± 0.10, and 3.80 ± 0.31 μM, respectively) and had high potency inhibiting [(3)H]dopamine uptake (K(i) = 0.028 ± 0.001, 0.046 ± 0.008, 0.043 ± 0.004 μM, respectively), but lacked affinity at nicotinic receptors. Although the trans-isomers did not alter methamphetamine-evoked dopamine release, UKCP-110 inhibited (IC(50) = 1.8 ± 0.2 μM; I(max) = 67.18 ± 6.11 μM) methamphetamine-evoked dopamine release. At high concentrations, UKCP-110 also increased extracellular dihydroxyphenylacetic acid. It is noteworthy that UKCP-110 decreased the number of methamphetamine self-infusions, while having no effect on food-reinforced behavior or the methamphetamine stimulus cue. Thus, UKCP-110 represents a new lead in the development of novel pharmacotherapies for the treatment of methamphetamine abuse.

Dataset Information

Cis-1-Benzyl-pyrrolidine-2,5-dicarbonitrile.

Publications

cis-1-Benzyl-pyrrolidine-2,5-dicarbonitrile.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets