The harmful chemistry behind "krokodil": Street-like synthesis and product analysis.
"Krokodil" is the street name for a drug, which has been attracting media and researchers attention due to its increasing spread and extreme toxicity. "Krokodil" is a homemade injectable mixture being used as a cheap substitute for heroin. Its use begun in Russia and Ukraine, but it is being spread throughout other countries. The starting materials for "krokodil" synthesis are tablets containing codeine, caustic soda, gasoline, hydrochloric acid, iodine from disinfectants and red phosphorus from matchboxes, all of which are easily available in a retail market or drugstores. The resulting product is a light brown liquid that is injected without previous purification. Herein, we aimed to understand the chemistry behind "krokodil" synthesis by mimicking the steps followed by people who use this drug. The successful synthesis was assessed by the presence of desomorphine and other two morphinans. An analytical gas chromatography-electron impact/mass spectrometry (GC-EI/MS) methodology for quantification of desomorphine and codeine was also developed and validated. The methodologies presented herein provide a representative synthesis of "krokodil" street samples and the application of an effective analytical methodology for desomorphine quantification, which was the major morphinan found. Further studies are required in order to find other hypothetical by-products in "krokodil" since these may help to explain signs and symptoms presented by abusers.
UCIBIO-REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal; Department of Legal Medicine and Forensic Sciences, Faculty of Medicine, University of Porto, Porto, Portugal; EPSJV - Polytechnic School of Health Joaquim Venâncio, Oswaldo Cruz Foundation, Rio de Janeiro, Brazil. Electronic address: manuhpa@hotmail.com.
Emanuele Amorim
EA
Alves
REQUIMTE, Department of Chemical Sciences, Laboratory of Applied Chemistry, Faculty of Pharmacy, University of Porto, Porto, Portugal.
José Xavier
JX
Soares
Center of Medical Chemistry (CEQUIMED-UP), Faculty of Pharmacy, University of Porto, Porto, Portugal; Interdisciplinary Center of Marine and Environmental Investigation (CIIMAR/CIMAR), Porto, Portugal.
Carlos Manuel
CM
Afonso
CVO - Addiction Research Centre, Utrecht, Netherlands; Department of Addictology, 1st Faculty of Medicine, Charles University in Prague and General University Hospital in Prague, Czech Republic.
Jean-Paul C
JC
Grund
Department of Legal Medicine and Forensic Sciences, Faculty of Medicine, University of Porto, Porto, Portugal.
Ana Sofia
AS
Agonia
Center of Medical Chemistry (CEQUIMED-UP), Faculty of Pharmacy, University of Porto, Porto, Portugal.
Sara Manuela
SM
Cravo
Department of Analytical Chemistry, Chemistry Institute, Fluminense Federal University, Niterói, Brazil.
Annibal Duarte Pereira
ADP
Netto
UCIBIO-REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal.
Félix
F
Carvalho
UCIBIO-REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal; Department of Legal Medicine and Forensic Sciences, Faculty of Medicine, University of Porto, Porto, Portugal; IINFACTS - Institute of Research and Advanced Training in Health Sciences and Technologies, Department of Sciences, University Institute of Health Sciences (IUCS), CESPU, CRL, Gandra, Portugal. Electronic address: ricardinis@med.up.pt.
Ricardo Jorge
RJ
Dinis-Oliveira
D002853:Chromatography, Liquid; D003061:Codeine / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D053593:Forensic Toxicology; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D013287:Illicit Drugs / Q000138:chemical synthesis*; D057230:Limit of Detection; D015819:Substance Abuse, Intravenous
D013287:Illicit Drugs; C000599494:desomorphine; D003061:Codeine
Desomorphine; GC-EI/MS analysis; Opioid abuse; “Krokodil” synthesis