Nuclear magnetic resonance and molecular orbital study of some cocaine analogues

Anu J. Airaksinen; Kari A. Tuppurainen; Simo E. Lötjönen; Matthias Niemitz; Meixiang Yu; Jouko J. Vepsäläinen; Reino Laatikainen; Jukka Hiltunen; Kim A. Bergström

doi:10.1016/S0040-4020(99)00577-3

Nuclear magnetic resonance and molecular orbital study of some cocaine analogues

Anu J. Airaksinen, Kari A. Tuppurainen, Simo E. Lötjönen, Matthias Niemitz, Meixiang Yu, Jouko J. Vepsäläinen, Reino Laatikainen, Jukka Hiltunen, Kim A. Bergström

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

¹H NMR spectra of (-)-cocaine and some of its derivatives (α-CPT, β- CPT, nor-β-CIT, cocaine-HCl and ecgonine-HCl) were analysed and the spectral parameters were used for conformational analysis of the compounds in conjunction with theoretical HF/6-31G*, MMP2, AM1 and molecular dynamics calculations. Comparison of the experimental and theoretical data reveals that the compounds are predominantly in a rigid chair conformation, which is rather similar for all compounds. No large differences were found in the dynamical behaviour of the molecules. The performance of the Haasnoot and Altona equations is discussed.

Original language	English (US)
Pages (from-to)	10537-10546
Number of pages	10
Journal	Tetrahedron
Volume	55
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4020(99)00577-3
State	Published - Aug 20 1999

Keywords

Cocaine analogues
Conformation
Molecular modelling
NMR

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/S0040-4020(99)00577-3

Cite this

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title = "Nuclear magnetic resonance and molecular orbital study of some cocaine analogues",

abstract = " 1H NMR spectra of (-)-cocaine and some of its derivatives (α-CPT, β- CPT, nor-β-CIT, cocaine-HCl and ecgonine-HCl) were analysed and the spectral parameters were used for conformational analysis of the compounds in conjunction with theoretical HF/6-31G*, MMP2, AM1 and molecular dynamics calculations. Comparison of the experimental and theoretical data reveals that the compounds are predominantly in a rigid chair conformation, which is rather similar for all compounds. No large differences were found in the dynamical behaviour of the molecules. The performance of the Haasnoot and Altona equations is discussed.",

keywords = "Cocaine analogues, Conformation, Molecular modelling, NMR",

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doi = "10.1016/S0040-4020(99)00577-3",

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T1 - Nuclear magnetic resonance and molecular orbital study of some cocaine analogues

AU - Airaksinen, Anu J.

AU - Tuppurainen, Kari A.

AU - Lötjönen, Simo E.

AU - Niemitz, Matthias

AU - Yu, Meixiang

AU - Vepsäläinen, Jouko J.

AU - Laatikainen, Reino

AU - Hiltunen, Jukka

AU - Bergström, Kim A.

PY - 1999/8/20

Y1 - 1999/8/20

N2 - 1H NMR spectra of (-)-cocaine and some of its derivatives (α-CPT, β- CPT, nor-β-CIT, cocaine-HCl and ecgonine-HCl) were analysed and the spectral parameters were used for conformational analysis of the compounds in conjunction with theoretical HF/6-31G*, MMP2, AM1 and molecular dynamics calculations. Comparison of the experimental and theoretical data reveals that the compounds are predominantly in a rigid chair conformation, which is rather similar for all compounds. No large differences were found in the dynamical behaviour of the molecules. The performance of the Haasnoot and Altona equations is discussed.

AB - 1H NMR spectra of (-)-cocaine and some of its derivatives (α-CPT, β- CPT, nor-β-CIT, cocaine-HCl and ecgonine-HCl) were analysed and the spectral parameters were used for conformational analysis of the compounds in conjunction with theoretical HF/6-31G*, MMP2, AM1 and molecular dynamics calculations. Comparison of the experimental and theoretical data reveals that the compounds are predominantly in a rigid chair conformation, which is rather similar for all compounds. No large differences were found in the dynamical behaviour of the molecules. The performance of the Haasnoot and Altona equations is discussed.

KW - Cocaine analogues

KW - Conformation

KW - Molecular modelling

KW - NMR

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U2 - 10.1016/S0040-4020(99)00577-3

DO - 10.1016/S0040-4020(99)00577-3

M3 - Article

AN - SCOPUS:0033588154

SN - 0040-4020

VL - 55

SP - 10537

EP - 10546

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

Nuclear magnetic resonance and molecular orbital study of some cocaine analogues

Abstract

Keywords

ASJC Scopus subject areas

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