title: The harmful chemistry behind krokodil (desomorphine) synthesis and mechanisms of toxicity.
abstract: "Krokodil" is the street name for the homemade injectable mixture that has been used as a cheap substitute for heroin. Its use begun in Russia and Ukraine and nowadays is being spread over several other countries. Desomorphine is the semi-synthetic opioid claimed to be the main component of krokodil and considered to be responsible for its psychoactive characteristics. The starting materials for desomorphine synthesis are codeine tablets, alkali solutions, organic solvent, acidified water, iodine and red phosphorus, all of which are easily available in retail outlets, such as supermarkets, drugstores, etc. The resulting product is a light brown liquid that is called krokodil. People who inject krokodil present a great variety of serious signs and symptoms, including thrombophlebitis, ulcerations, gangrene, and necrosis, quickly evolving to limb amputation and death. These effects are thought to result from the toxic components produced as byproducts during the homemade drug synthesis. In this work, we reviewed several aspects of krokodil use, including its epidemiology, pharmacology and the chemical properties of the main active ingredient (desomorphine). To enhance our understanding of the clinical and toxic effects and to support the implementation of harm reduction measures, we also describe the "bathtub chemistry" of krokodil and the content of the final solution.
authors.affiliation: Department of Legal Medicine and Forensic Sciences, Faculty of Medicine, University of Porto, Porto, Portugal; REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal; EPSJV-Polythecnical School of Health Joaquim Venâncio, Oswaldo Cruz Foundation, Rio de Janeiro, Brazil. Electronic address: manuhpa@hotmail.com.
authors.forename: Emanuele Amorim
authors.initials: EA
authors.lastname: Alves
authors.affiliation: DoA-CUNI-Addiction Research Centre, Utrecht, The Netherlands; Department of Addictology, 1st Faculty of Medicine, Charles University in Prague and General University Hospital in Prague, Prague, Czech Republic.
authors.forename: Jean-Paul Cornelis
authors.initials: JP
authors.lastname: Grund
authors.affiliation: 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.
authors.forename: Carlos Manuel
authors.initials: CM
authors.lastname: Afonso
authors.affiliation: Department of Analytical Chemistry, Chemistry Institute, Fluminense Federal University, Niterói, Brazil.
authors.forename: Annibal Duarte Pereira
authors.initials: AD
authors.lastname: Netto
authors.affiliation: REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal.
authors.forename: Félix
authors.initials: F
authors.lastname: Carvalho
authors.affiliation: Department of Legal Medicine and Forensic Sciences, Faculty of Medicine, University of Porto, Porto, Portugal; REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal; IINFACTS-Institute of Research and Advanced Training in Health Sciences and Technologies, Department of Sciences, Advanced Institute of Health Sciences-North (ISCS-N), CESPU, CRL, Gandra, Portugal. Electronic address: ricardinis@sapo.pt.
authors.forename: Ricardo Jorge
authors.initials: RJ
authors.lastname: Dinis-Oliveira
mesh_terms: D000673:Amputation, Traumatic / Q000139:chemically induced; D003061:Codeine / Q000009:adverse effects / Q000031:analogs & derivatives* / Q000737:chemistry; D005734:Gangrene / Q000139:chemically induced; D006801:Humans; D013287:Illicit Drugs / Q000009:adverse effects* / Q000737:chemistry*; D015394:Molecular Structure; D009336:Necrosis / Q000139:chemically induced; D020258:Neurotoxicity Syndromes / Q000209:etiology; D010020:Osteonecrosis / Q000139:chemically induced; D012867:Skin / Q000473:pathology; D015819:Substance Abuse, Intravenous / Q000150:complications*
chemical_list: D013287:Illicit Drugs; C000599494:desomorphine; D003061:Codeine
keywords: Desomorphine; Krokodil synthesis; Opioids; People who inject drugs; Signs and symptoms