The Isolation and Identification of Precursors and Reaction Products in the Clandestine Manufacture of Methaqualone and Mecloqualone

Angelos, Sanford A.; Meyers, John A.

doi:10.1520/jfs11044j

Cited by 18 publications

(7 citation statements)

References 3 publications

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“…The synthesis of methaqualone and related quinazolinones is not difficult (Angelos & Meyers 1985;Soliman et al 1978) and obviates the need for exogenous sources of methaqualone. Two homologues of methaqualone (mecloqualone, nitromethaqualone) which have been in clinical use in Europe are reported to be synthesised by clandestine laboratories in the United States (Daenens & Van Boven 1976Ĩ ntoxication is typified by ataxia and lethargy, although initially a period of disinhibited stimulation may be noted.…”

Section: Methaqualone Derivativesmentioning

confidence: 99%

‘Designer Drugs’

Buchanan

Brown

1988

Medical Toxicology

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'Designer drugs' are substances intended for recreational use which are derivatives of approved drugs so as to circumvent existing legal restrictions. The term as popularised by the lay press lacks precision. Contrary to the popular belief that 'designer drugs' are original creations, the majority of these agents are 'borrowed' from legitimate pharmaceutical research. They merely represent the most recent developments in the evolution of mind-altering chemicals. The most extensively studied class of psychoactive compounds is the phenylethylamines (mescaline analogues). This class includes catecholamines, therapeutic agents and numerous illicit derivatives. Subtle alterations of the phenylethylamine molecule give rise to a spectrum of pharmacological properties ranging from pure sympathomimetic stimulation to primarily psychoactive effects. Although most of these compounds are only of historical interest, amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine (MDA), and 3,4-methylenedioxymethamphetamine (MDMA) continue to be used recreationally. Many deaths have been ascribed to this class of compounds. In overdose the differences between these compounds blur and the clinical presentation is similar to that of amphetamine overdose characterised by tachycardia, hypertension, hyperthermia, diaphoresis, mydriasis, agitation, muscle rigidity, and hyper-reflexia. Death usually results from arrhythmias, hyperthermia or intracerebral haemorrhage. Treatment is aggressive and supportive with careful attention to temperature, blood pressure and seizure control. Synthetic opioid derivatives, which represent the second major class of 'designer drugs', are derivatives of fentanyl (e.g. alpha-methylfentanyl, 3-methylfentanyl) or pethidine (meperidine) and are extremely potent compounds responsible for numerous overdose deaths. Attempts to synthesise pethidine have resulted in the accidental production of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine), a compound which is metabolised in the brain by the monoamine oxidase system to a toxic intermediate (MPP+) which selectively destroys the sustantia nigra, resulting in the rapid onset of severe Parkinsonian symptoms. Naloxone will antagonise the opiate effects of this drug class, although high doses may be required. Arylhexylamines constitute the third class of 'designer drugs'. The predominant member of this class is phencyclidine (PCP), a derivative of the anaesthetic ketamine. This unique class of psychoactive agents exhibits broad and complex pharmacological effects.(ABSTRACT TRUNCATED AT 400 WORDS)

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Section: Methaqualone Derivativesmentioning

confidence: 99%

‘Designer Drugs’

Buchanan

Brown

1988

Medical Toxicology

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“…They holds a broad range of biological activity including analgesic, antimalarial, anti‐inflammatory, anti‐convulsant, antimycobacterial, anticancer, antihypertensive and anticancer activities . For example, quinazolinone drug, methaqualone A was widely used as a sedative‐hypnotic agent . Additionally, some of these compounds like B and C , used as a kinase and dihydrofolate reductase inhibitors .…”

Section: Introductionmentioning

confidence: 99%

“…[1] For example, quinazolinone drug, methaqualone A was widely used as a sedative-hypnotic agent. [2] Additionally, some of these compounds like B and C, used as a kinase and dihydrofolate reductase inhibitors. [3] Proquazone D and Fluproquazone E used in the treatment of rheumatoid arthritis by the inhibition of prostaglandin synthesis.…”

Section: Introductionmentioning

confidence: 99%

Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3H)‐ones in Water

et al. 2018

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A novel water assisted strategy has been developed for the synthesis of quinazolinones by the reaction of o‐aminobenzamides 1 with benzyl alcohols 2 using NaCl in regioselective manner under microwave radiation (MW). NaCl and water plays an unprecedented and vital role in the reaction. NaCl create more space for the reactants in aqueous media and bring them in very close proximity for C−N bond formation through “kosmotropes perturbation”. There is no need of any metal, ligand and base for further activation of the reactants in the reaction because water trigger the reaction via “ambiphilic dual activation” of reactants through hydrogen bond accepter and donor ability in the pertinent C−N bond forming steps in the reaction. This “kosmotropes perturbation” and “ambiphilic dual activation” is the accountable attribute for making a new water‐assisted strategy. Several controlled experiments have been carried out to establish the suitable mechanism and stipulation of the reactions. The process illustrated significant selectivity for quinazolinones over dihydrogenated quinazolinones.

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“…Since the discovery of methaqualone I ( Figure 1 ) as a sedative hypnotic [ 19 , 20 ], the search for new anticonvulsant drugs with reduced toxicity and fewer side effects has been continuous. Our literature survey revealed that replacement of the methyl group by some other functionalities such as alkylthiomethyl or alkyloxymethyl groups reportedly yielded structural analogues which retained the anticonvulsant activity [ 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticonvulsant Activity of Some Quinazolin-4-(3H)-one Derivatives

2008

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A number of 3-substituted-2-(substituted-phenoxymethyl) quinazolin-4(3H)-one derivatives have been synthesized. Their structures have been elucidated on the basis of elemental analyses and spectroscopic studies (IR, 1H-NMR, MS). A preliminary evaluation of the anticonvulsant properties of the prepared compounds has indicated that some of them exhibit moderate to significant activity, compared to a diazepam standard.

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The Isolation and Identification of Precursors and Reaction Products in the Clandestine Manufacture of Methaqualone and Mecloqualone

Cited by 18 publications

References 3 publications

‘Designer Drugs’

‘Designer Drugs’

Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3H)‐ones in Water

Synthesis and Anticonvulsant Activity of Some Quinazolin-4-(3H)-one Derivatives

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