Rapid experimental and computational determination of phenethylamine drug analogue lipophilicity

Ethan M. McBride; Amanda Kretsch; Luis K. Garibay; Katie Brigance; Benji Frey; Brandon Buss; Guido F. Verbeck

doi:10.1016/j.forc.2016.07.004

Rapid experimental and computational determination of phenethylamine drug analogue lipophilicity

Ethan M. McBride, Amanda Kretsch, Luis K. Garibay, Katie Brigance, Benji Frey, Brandon Buss, Guido F. Verbeck

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

6 Scopus citations

Abstract

In this work, synthetic phenethylamine drug analogues were synthesized using a shotgun method and rapidly characterized via electrospray ionization-mass spectrometry (ESI-MS) for structural confirmation, determination of partition coefficients (Log P) by a chloroform/water system, and evaluation of blood–brain barrier permeability by parallel artificial membrane permeability assay (PAMPA-BBB) to determine apparent permeability (P_app). Computational methods to validate the method and calculate theoretical Log P values and molecular lipophilic potentials (MLP) were used to supplement experimental data. These data were combined with Lipinski's Rule of Five in a searchable ACD/Labs database for quick reference by forensic practitioners.

Original language	English (US)
Pages (from-to)	58-65
Number of pages	8
Journal	Forensic Chemistry
Volume	1
DOIs	https://doi.org/10.1016/j.forc.2016.07.004
State	Published - Aug 1 2016
Externally published	Yes

Keywords

Analogue
Apparent permeability
Forensic
PAMPA
Partition coefficient
Phenethylamine

ASJC Scopus subject areas

Analytical Chemistry
Pathology and Forensic Medicine
Spectroscopy
Physical and Theoretical Chemistry
Materials Chemistry
Law

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10.1016/j.forc.2016.07.004

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title = "Rapid experimental and computational determination of phenethylamine drug analogue lipophilicity",

abstract = "In this work, synthetic phenethylamine drug analogues were synthesized using a shotgun method and rapidly characterized via electrospray ionization-mass spectrometry (ESI-MS) for structural confirmation, determination of partition coefficients (Log P) by a chloroform/water system, and evaluation of blood–brain barrier permeability by parallel artificial membrane permeability assay (PAMPA-BBB) to determine apparent permeability (Papp). Computational methods to validate the method and calculate theoretical Log P values and molecular lipophilic potentials (MLP) were used to supplement experimental data. These data were combined with Lipinski's Rule of Five in a searchable ACD/Labs database for quick reference by forensic practitioners.",

keywords = "Analogue, Apparent permeability, Forensic, PAMPA, Partition coefficient, Phenethylamine",

author = "McBride, {Ethan M.} and Amanda Kretsch and Garibay, {Luis K.} and Katie Brigance and Benji Frey and Brandon Buss and Verbeck, {Guido F.}",

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doi = "10.1016/j.forc.2016.07.004",

language = "English (US)",

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TY - JOUR

T1 - Rapid experimental and computational determination of phenethylamine drug analogue lipophilicity

AU - McBride, Ethan M.

AU - Kretsch, Amanda

AU - Garibay, Luis K.

AU - Brigance, Katie

AU - Frey, Benji

AU - Buss, Brandon

AU - Verbeck, Guido F.

PY - 2016/8/1

Y1 - 2016/8/1

N2 - In this work, synthetic phenethylamine drug analogues were synthesized using a shotgun method and rapidly characterized via electrospray ionization-mass spectrometry (ESI-MS) for structural confirmation, determination of partition coefficients (Log P) by a chloroform/water system, and evaluation of blood–brain barrier permeability by parallel artificial membrane permeability assay (PAMPA-BBB) to determine apparent permeability (Papp). Computational methods to validate the method and calculate theoretical Log P values and molecular lipophilic potentials (MLP) were used to supplement experimental data. These data were combined with Lipinski's Rule of Five in a searchable ACD/Labs database for quick reference by forensic practitioners.

AB - In this work, synthetic phenethylamine drug analogues were synthesized using a shotgun method and rapidly characterized via electrospray ionization-mass spectrometry (ESI-MS) for structural confirmation, determination of partition coefficients (Log P) by a chloroform/water system, and evaluation of blood–brain barrier permeability by parallel artificial membrane permeability assay (PAMPA-BBB) to determine apparent permeability (Papp). Computational methods to validate the method and calculate theoretical Log P values and molecular lipophilic potentials (MLP) were used to supplement experimental data. These data were combined with Lipinski's Rule of Five in a searchable ACD/Labs database for quick reference by forensic practitioners.

KW - Analogue

KW - Apparent permeability

KW - Forensic

KW - PAMPA

KW - Partition coefficient

KW - Phenethylamine

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SP - 58

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JO - Forensic Chemistry

JF - Forensic Chemistry

ER -

Rapid experimental and computational determination of phenethylamine drug analogue lipophilicity

Abstract

Keywords

ASJC Scopus subject areas

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