Literature DB >> 423195

Optically pure (+)-nicotine from (+/-)-nicotine and biological comparisons with (-)-nicotine.

M D Aceto, B R Martin, I M Uwaydah, E L May, L S Harris, C Izazola-Conde, W L Dewey, T J Bradshaw, W C Vincek.   

Abstract

Optically pure (+)-nicotine has been obtained from (+/-)-nicotine using a combination of d-tartaric acid and di-p-toluoyl-l-tartaric acid. As the di-d-tartrate salt, (+)-nicotine is less potent than (-)-nicotine di-l-tartrate in producing lethality in mice, on blood pressure in anesthetized rats, and in the isolated guinea-pig ileum, indicating substantial stereospecificity for nicotine receptors. Potency ratios are 0.14, 0.06, and 0.019, respectively.

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Year:  1979        PMID: 423195     DOI: 10.1021/jm00188a009

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  11 in total

1.  Separation of d-(+)-Nicotine from a Racemic Mixture by Stereospecific Degradation of the l-(-) Isomer with Pseudomonas putida.

Authors:  M C Detraglia; A M Tometsko
Journal:  Appl Environ Microbiol       Date:  1980-05       Impact factor: 4.792

2.  Relations among acute and chronic nicotine administration, short-term memory, and tactics of data analysis.

Authors:  Brian D Kangas; Marc N Branch
Journal:  J Exp Anal Behav       Date:  2012-09       Impact factor: 2.468

3.  Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Authors:  Charles E Hendrick; Katie J Bitting; Seoyoung Cho; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

4.  Comparative pharmacology of nicotine and ABT-418, a new nicotinic agonist.

Authors:  M I Damaj; K R Creasy; S P Welch; J A Rosecrans; M D Aceto; B R Martin
Journal:  Psychopharmacology (Berl)       Date:  1995-08       Impact factor: 4.530

5.  A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex.

Authors:  J R Copeland; A Adem; P Jacob; A Nordberg
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  1991-02       Impact factor: 3.000

6.  Plasma concentrations of nicotine in rats during tolerance and chronic exposure studies.

Authors:  B F Thomas; E R Bowman; S M Tucker; M D Aceto
Journal:  Eur J Drug Metab Pharmacokinet       Date:  1988 Oct-Dec       Impact factor: 2.441

7.  Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: application to the synthesis of nicotine analogues.

Authors:  Kun Huang; Francisco G Merced; Margarita Ortiz-Marciales; Héctor J Meléndez; Wildeliz Correa; Melvin De Jesús
Journal:  J Org Chem       Date:  2008-05-01       Impact factor: 4.354

8.  Characteristics of conditioned taste aversion produced by nicotine in rats.

Authors:  R Kumar; J A Pratt; I P Stolerman
Journal:  Br J Pharmacol       Date:  1983-05       Impact factor: 8.739

9.  In vivo pharmacological effects of dihydro-beta-erythroidine, a nicotinic antagonist, in mice.

Authors:  M I Damaj; S P Welch; B R Martin
Journal:  Psychopharmacology (Berl)       Date:  1995-01       Impact factor: 4.530

10.  Discriminative stimulus properties of the optical isomers of nicotine.

Authors:  L T Meltzer; J A Rosecrans; M D Aceto; L S Harris
Journal:  Psychopharmacology (Berl)       Date:  1980       Impact factor: 4.530

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