A facile and improved synthesis of desomorphine and its deuterium-labeled analogue

Srimurugan, Sankareswaran; Su, Chi-Ju; Shu, Hun‐Chi; Murugan, Kaliyappan; Chen, Chinpiao

doi:10.1007/s00706-011-0635-y

Cited by 10 publications

(11 citation statements)

References 22 publications

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“…The final demethylation of desocodeine ( 26 ) was performed through an efficient protocol using 1.5 equiv of BBr 3 , yielding desomorphine in acceptable yield and very high purity. The overall yield of the synthesis was 38%, and the authors claim that no column purification was required in any step …”

Section: Desomorphine (Krokodil)mentioning

confidence: 99%

“…172,190,223,224 On the other hand, a modification of this process has been reported by Srimurugan that achieves a higher yield and purity without obtaining impurities or byproducts (Scheme 5). 225 For this synthesis, a codeine free base was generated from codeine phosphate, followed by a reaction with mesyl chloride, affording the corresponding mesylate 32 in excellent yield. The treatment of 6-mesylcodeine (32) with 2 equiv of LiAlH 4 in THF at room temperature for a short time afforded dehydrodesocodeine (33) in high yield.…”

Section: Desomorphine (Krokodil)mentioning

confidence: 99%

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DARK Classics in Chemical Neuroscience: Heroin and Desomorphine

Mella

Romero-Parra

Recabarren‐Gajardo

2020

ACS Chem. Neurosci.

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Opioids are arguably one of the most important pharmacologic classes, mainly due to their rich history, their useful and potent analgesic effects, and also, just as importantly, their "Dark Side", constituted by their reinforcing properties that have led countless of users to a spiral of addiction, biological dependence, tolerance, withdrawal syndromes, and death. Among the most significant abused and addictive known opioids are heroin and desomorphine, both synthetic derivatives of morphine that belong to the 4,5-epoxymorphinan structural chemical group of the opioid family drugs. These agents share not only structural, pharmacological, and epidemiological features but also a common geographical distribution. A drop in Afghan heroin production and its "exports" to Russia gave rise to widespread consumption of desomorphine in ex-Soviet republics during the first decade of the 21st century, representing an economical and accessible alternative for misusers to this sort of derivative. Herein we review the state of the art of history, chemistry and synthesis, pharmacology, and impact on society of these "cursed cousins".

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Section: Desomorphine (Krokodil)mentioning

confidence: 99%

Section: Desomorphine (Krokodil)mentioning

confidence: 99%

DARK Classics in Chemical Neuroscience: Heroin and Desomorphine

Mella

Romero-Parra

Recabarren‐Gajardo

2020

ACS Chem. Neurosci.

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“…[43][44][45] The process of navigating and redefining the findings was iterative, and with each stage reflexive, by fine tuning and repeating steps so as to ensure comprehensive coverage of available literature. [21,23,46,47] Pharmaceutical manufacturers continue to develop intended and unintended barriers to tampering and dis-incentivization of misuse by using flavours, dyes, fillers, binders in oral formulations, coating, beador crush-resistant compounds, time-release matrices, gel capsules, and producing combination products with undesirable actives such as aminophen, aspirin, ibuprofen, and caffeine. [40][41][42] and is hereafter presented as a broad based 'narrative review' design.…”

Section: The Scoping Reviewmentioning

confidence: 99%

“…[21] Tampering in the form of crushing, separation from undesirable actives, overcoming timerelease formulations, purification and chemical alteration of formulations, along with advice around optimal use (dosage, route) are readily available on the Internet. [21,23,46,47] Pharmaceutical manufacturers continue to develop intended and unintended barriers to tampering and dis-incentivization of misuse by using flavours, dyes, fillers, binders in oral formulations, coating, beador crush-resistant compounds, time-release matrices, gel capsules, and producing combination products with undesirable actives such as aminophen, aspirin, ibuprofen, and caffeine. [18,[22][23][24]46,[48][49][50][51][52] Despite these efforts to minimize abuse potential and harm, drug users favour simplistic procedures to alter formulations [21] and generally are deterred by homemade drug solutions which are difficult to produce [18] or inject.…”

Section: The Scoping Reviewmentioning

confidence: 99%

Kitchen chemistry: A scoping review of the diversionary use of pharmaceuticals for non‐medicinal use and home production of drug solutions

Hout

2014

Drug Testing and Analysis

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Misuse of pharmaceuticals is of increasing drug policy and public health concern. A scoping review was conducted on the diversionary use of pharmaceuticals for non-medicinal use and home production of drug solutions. The research question was broad: What is known from the existing literature about the diversion of pharmaceuticals for non-medicinal use and for home production of drug solutions? The scoping process centred on the systematic selection, collection, and summarization of extant knowledge within this broad thematic remit. One hundred and thirty-four records were grouped into discrete thematic categories namely: non medicinal use and tampering with pharmaceuticals, oral misuse of codeine cough syrups, homemade drug solutions, and home-produced drug-related harms in the narrative review design. Forms of abuse of codeine cough syrup include mixtures with alcohol or soft drinks ('Purple Drank'), with kratom leaves ('Kratom cocktails'), or chemically altered to extract dextromorphan ('Lemon Drop'). Production of homemade opiates ('Cheornaya', 'Kolyosa', Himiya', 'Braun', 'Krokodil'), methamphetamine ('Vint', 'Pervitin'), methcathinone ('Jeff'), and cathinone ('Boltushka') are described. Displacement patterns between the non-medical use of pharmaceuticals, commercial, and homemade drugs appear dependent on availability of opiates, prescribing practices, supervision of substitution drug dosing, availability of cheap ingredients, policing, and awareness of harms. Adverse health and social consequences relate to the use of unknown and contaminated (end) substances, injecting practices, redosing, medical complications, and death. The review highlights a public health imperative requiring a multidisciplinary approach to quantify potential impact and required integrated policy responses incorporating international regulation, enforcement, health surveillance and service delivery.

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“…]-desomorphine were synthesized by the synthetic routes 37 shown in Supporting Information (Schemes S1 and S2). The purity of all the synthesized compounds were found to be >99% by GC-MS.…”

Section: Reagents and Chemicalsmentioning

confidence: 99%

Sol-gel Titania-Coated Needles for Solid Phase Dynamic Extraction-GC/MS Analysis of Desomorphine and Desocodeine

Srimurugan

Chen

et al. 2011

ANAL. SCI.

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Novel sol-gel titania film coated needles for solid-phase dynamic extraction (SPDE)-GC/MS analysis of desomorphine and desocodeine are described. The high thermal stability of titania film permits efficient extraction and analysis of poorly volatile opiate drugs. The influences of sol-gel reaction time, coating layer, extraction and desorption time and temperature on the SPDE needle performance were investigated. The deuterium labeled internal standard was introduced either during the extraction of analyte or directly injected to GC after the extraction process. The latter method was shown to be more sensitive for the analysis of water and urine samples containing opiate drugs. The proposed conditions provided a wide linear range (from 5 -5000 ppb), and satisfactory linearity, with R 2 values from 0.9958 to 0.9999, and prominent sensitivity, LOQs (1.0 -5.0 ng/g). The sol-gel titania film coated needle with SPDE-GC/MS will be a promising technique for desomorphine and desocodeine analysis in urine.

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A facile and improved synthesis of desomorphine and its deuterium-labeled analogue

Cited by 10 publications

References 22 publications

DARK Classics in Chemical Neuroscience: Heroin and Desomorphine

DARK Classics in Chemical Neuroscience: Heroin and Desomorphine

Kitchen chemistry: A scoping review of the diversionary use of pharmaceuticals for non‐medicinal use and home production of drug solutions

Sol-gel Titania-Coated Needles for Solid Phase Dynamic Extraction-GC/MS Analysis of Desomorphine and Desocodeine

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