A neolignan-type impurity arising from the peracid oxidation reaction of anethole in the surreptitious synthesis of 4-methoxyamphetamine (PMA)

Waumans, Dieter; Hermans, Bas; Bruneel, Noël; Tytgat, Jan

doi:10.1016/j.forsciint.2004.02.033

Cited by 8 publications

(8 citation statements)

References 15 publications

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“…6). In every case (11B) was the major isomer, followed by the earlier eluting (11A) and then the later eluting (11C); this pattern closely follows the formation of anetholederived furans [13].…”

Section: Resultsmentioning

confidence: 60%

“…Although the unknown was detected in the acetone mediated oxidation of isosafrole, the acetonide (5) interfered with the isolation of the unknown and consequently dichloromethane was the reaction solvent of choice. The optimal molar ratio of isosafrole (3) to hydrogen peroxide to formic acid was determined to be 1:5:13 which was identical to that used by Waumans et al for the performic acid oxidation of anethole (7) [13] and similar to several illicit recipes. In most cases the yield of the suspected furan (11) was approximately 5-10% from isosafrole (3).…”

Section: Resultsmentioning

confidence: 89%

“…It was speculated that the two peaks might represent two of four possible diastereomers of the condensation product (12) derived from MDP2P (4) (the major product of hydrolytic dehydration) and isosafrole glycol (13) (an oxygenated product reported in the peracid oxidation of isosafrole (3) [11]) (Scheme 4). Support for this theory was gained when pure isosafrole glycol (13) (synthesised by permanganate oxidation of isosafrole (3)) was heated in dilute hydrochloric acid.…”

Section: Resultsmentioning

confidence: 99%

“…Waumans et al recently reported the detection of isomers of 2,4-dimethyl-3,5-bis(4-methoxyphenyl)tetrahydrofuran in paramethoxyamphetamine (PMA) seizures and confirmed that its presence is a result of peracid oxidation of anethole (7) (Scheme 2) [13]. Ring opening of the epoxide produced by peracid oxidation of anethole is believed to produce a stabilised benzylic carbocation that can be trapped by another molecule of anethole, followed by ring closure to give the furan by-product.…”

Section: Introductionmentioning

confidence: 89%

See 3 more Smart Citations

Chemical markers from the peracid oxidation of isosafrole

Cox

Klass

Morey

et al. 2008

Forensic Science International

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Section: Resultsmentioning

confidence: 60%

Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 89%

See 2 more Smart Citations

Chemical markers from the peracid oxidation of isosafrole

Cox

Klass

Morey

et al. 2008

Forensic Science International

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“…It is impossible to distinguish Chinese star anise from Japanese star anise in its appearance only, due to morphological similarities between the species. Nevertheless, the Chinese star anise has been reported to be toxic in some pediatric cases (9), and its main component trans-anethole may be a chemical precursor to paramethoxyamphetamine (PMA), an illicit drug with neurological and systemic noxious effects (10). Diluiting anethole with water-based liquid a spontaneous microemulsion, called "ouzo effect" which may have acted as a carrier for other substance and a promoter of the lung damage in the present case (11).…”

confidence: 96%

A bilateral pneumonia following Thai herbal inhaler compulsive use

Confalonieri¹

2015

sob

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SummaryTraditional herbal therapy is often underestimated as a possible cause of drug-induced lung diseases. We report the case of a 51 years old man who developed acute respiratory failure after abuse and misuse of a traditional Thai herbal inhaler. The composition of the herbal therapy was only partially known. However, we supposed that the menthol balm may have been responsible of the pulmonary lipoid inclusions and trans-anethole may have caused diffuse alveolar lung damage. KEY WORDS: diffuse parenchymal lung disease, herbal therapy, drug-induced lung disease, ARDS.A 51 years old man was admitted to the Cardiology Unit because of sudden chest pain, palpitations and shortness of breath. He was a worker in a manufacturing company without any particular dust or metal exposition. Moreover, he was an occasional drummer and a mild smoker, without a relevant past history. Until those sudden symptoms, he didn't have previously exercise limitation. At hospital cardiologists promptly diagnosed the rupture of a tendon cord of the mitral valve with severe mitral failure, and planned cardiosurgery. During this first hospitalization, the patient had some episodes of paroxysmal supra-ventricular tachycardia (max. 135 bpm), then solved by adenosine infusion. The patient developed a small "hospital-acquired pneumonia" at the right lower lobe, so an antibiotic therapy (levofloxacin 500mg os b.i.d.) was added at hospital discharge. After seven days from discharge, the patient was another time admitted to the hospital because of progressive dyspnea and hemoptysis. He had cyanosis, tachypnea, tachycardia, mild fever, but no apparent signs of heart failure. Radiology imaging (chest X-ray and thorax CT scan) showed bilateral shadows consistent with diffuse pneumonia (Figure 1). Other main findings at the second admission were: hypoxemia and hypocapnia (PaO2 50mmHg, PaCO2 33mmHg), elevated reactive C-protein (163 mg/L)), increased blood eosinophils (9.8%), normal D-dimer and BNP, negative autoimmunity. A bronchoscopy was then performed to obtain bronchoalveolar lavage (BAL) and lung transbronchial cryobpsies. The BAL resulted not diagnostically significant, nor an infectious agent was identified. The cryobpsy showed a picture typical of an inhalation pneumonia with lipid intracellular droplets in some alveolar macrophage, but without be really diagnostic for lipoid pneumonia (Figure 2). The pathologists observed also patchy organizing pneumonia and diffuse lung injury. So, the physicians questioned the patient again to realize which substances may have been inhaled quite recently, according to the quite rapid worsening of symptoms and development of bilateral pneumonia. After an accurate interrogation to the patient, we acknowledged that after the first episode of acute shortness of breath due to the rupture of mitralic tendon cord, the patient inhaled repeatedly a "natural" product given by a friend who was just come back from Thailand ( Figure 3). The product was a small cylinder containing a lipid balm basis underlying a vegeta...

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Synthesis of Deuterium Labeled (±)‐2,5‐Dimethoxyamphetamine (DMA), (±)‐4‐Bromo‐2,5‐Dimethoxyamphetamine (DOB), and (±)‐4‐Methoxyamphetamine (PMA) as Internal Standards for Quantitative Analyses by GC‐MS

Lin

Lua

et al. 2007

J Chinese Chemical Soc

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DMA, DOB and PMA are increasingly abused central nervous system stimulants with neurotoxic properties. In recent years, many controlled substance analogs (designer drugs) with a large variety of structures have reached the illegal market, making their identification difficult. Therefore, this work studies the synthesis of DOB‐d6, DMA‐d6 and PMA‐d3 as internal standards for use in gas chromatography‐mass spectrometry (GC‐MS) to identify controlled substances.

show abstract

A neolignan-type impurity arising from the peracid oxidation reaction of anethole in the surreptitious synthesis of 4-methoxyamphetamine (PMA)

Cited by 8 publications

References 15 publications

Chemical markers from the peracid oxidation of isosafrole

Chemical markers from the peracid oxidation of isosafrole

A bilateral pneumonia following Thai herbal inhaler compulsive use

Synthesis of Deuterium Labeled (±)‐2,5‐Dimethoxyamphetamine (DMA), (±)‐4‐Bromo‐2,5‐Dimethoxyamphetamine (DOB), and (±)‐4‐Methoxyamphetamine (PMA) as Internal Standards for Quantitative Analyses by GC‐MS

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