Illicit heroin manufacturing by-products:  capillary gas chromatographic determination and structural elucidation of narcotine- and norlaudanosine-related compounds

Allen, Andrew C.; Cooper, Donald A.; Moore, James M.; Gloger, Manfred; Neumann, Helmut

doi:10.1021/ac00278a072

Cited by 57 publications

(42 citation statements)

References 29 publications

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“…13: 7.19, 9.92 and 50.33 for the Tas, SWA and SEA methods, respectively. These compounds are formed by the N-acetylation followed by demethylation of morphine and codeine N-oxide, which are transient intermediates formed during the acetylation process [22]. Not surprisingly our data confirm the TFAA routes as milder, resulting in lower initial concentrations of these intermediate species and hence lower amounts of 11-13 and 15.…”

Section: Resultssupporting

confidence: 71%

“…26: AA: 57.21 and 1.5; TFAA: 3.52 and <0.05 for SWA and SEA, respectively) ( Table 3). The formation of 24 and 25 proceeds through the addition of acetic acid across the double bond in 27 and 28 [22]. The absence of these compounds in samples produced using TFAA can be explained by the absence of acetic acid and the smaller quantities of 27 and 28 present in the mixed anhydride system.…”

Section: Resultsmentioning

confidence: 99%

“…The absence of these compounds in samples produced using TFAA can be explained by the absence of acetic acid and the smaller quantities of 27 and 28 present in the mixed anhydride system. The formation of 26 proceeds through the precursor, noscapine N-oxide [22]. The increased abundance of this compound in the AA samples is believed to be a result of smaller quantities of noscapine N-oxide being formed during the TFAA synthesis.…”

Section: Resultsmentioning

confidence: 99%

“…The formation of 29 involves the acetylation of the secondary amine group in N-norlaudanosine [22], which is a function of nucleophile strength, with increased prevalence for attack at the trifluoroacetyl carbonyl, of the mixed anhydride formed in situ, increasing with the reactivity of the nucleophile [41]. Hence the TFAA procedure favours trifluoroacetylation, decreasing the amount of 29 observed.…”

Section: Resultsmentioning

confidence: 99%

See 3 more Smart Citations

A ‘cold synthesis’ of heroin and implications in heroin signature analysis

Odell

Skopec²,

McCluskey

2006

Forensic Science International

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Section: Resultssupporting

confidence: 71%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

A ‘cold synthesis’ of heroin and implications in heroin signature analysis

Odell

Skopec²,

McCluskey

2006

Forensic Science International

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“…Extraction with CHCl 3 and evaporation of the org. layer under vacuum yielded the desired product and some starting material (i.e., noscapine), which was purified by CC to give 3a (300 mg, 35%) ( [12]: yield 26%). Yellow oil.…”

mentioning

confidence: 99%

A Convenient Synthesis of Aryl-Substituted N-Carbamoyl/N-Thiocarbamoyl Narcotine and Related Compounds

Aggarwal¹,

Ghosh²,

Aneja³

et al. 2002

HCA

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The reaction of nornarcotine and 5-bromonornarcotine, synthesized from noscapine, with suitable aromatic isocyanates or isothiocyanates provides a general method for the synthesis of aryl-substituted N-carbamoyl or N-thiocarbamoylnarcotine and related compounds. Similarly, 15a has been prepared via the reduction of the lactone ring moiety of noscapine. Also, an improved procedure, which utilizes narcotine N-oxide ¥ HCl for generation of nornarcotine, is described.Introduction. ± Alkaloids and their analogs are important targets in chemical synthesis mainly because a large number of these compounds possess pronounced biological and pharmacological activities [1]. The basic isoquinoline-skeletal structure of various aporphine alkaloids, namely, (AE)-thaliporphine, (AE)-N-methylaurotetanine, and (AE)-isoboldine have been found to be of significant biological and biogenetic interest [2]. Noscapine, for example, a phthalide-isoquinoline alkaloid derived from opium, known for its antitussive action [3] [4] has recently been described as a prospective antineoplastic agent [5]. Ye et al. reported that noscapine has potent antitumor activity against solid lymphoid tumors induced in mice and, hence, exhibits outstanding therapeutic potential. In our earlier communication, we focussed on structural modulations of papaverine, a naturally occurring isoquinoline-based alkaloid isolated from Papaver somniferum [6], and reported the synthesis of urea/thiourea derivatives of papaverine, which were found to be more efficacious in terms of specificity and action in their antispasmodic effect. On similar lines of thought, we have also synthesized N-carbamoyl/N-thiocarbamoyl analogs of noscapine and other related compounds, which might prove as well to be more efficacious and less cytotoxic. Hence, new synthetic methodologies leading to novel antitumor agents are highly desired. In a recent publication from our laboratory [7], we have discussed the structure and the fragmentation patterns of narcotine and N-carbamoyl/N-thiocarbamoyl analogs of narcotine-related compounds. In the present paper, our interest circumscribes the synthetic procedures of N-demethylation and preparation of N-carbamoyl/N-thiocarbamoyl analogs of narcotine. It is the purpose of this communication to show how the target compound nornarcotine (3a) and other similar N-demethylated narcotine derivatives can be prepared in a few straightforward steps starting from noscapine (1a) and their further derivatization with aryl isocyanates and aryl isothiocyanates yielded the desired title compunds (Scheme 1).

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Biological and pharmacological activities of noscapine: Focusing on its receptors and mechanisms

Nourbakhsh

Askari

2021

BioFactors

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Noscapine has been mentioned as one of the effective drugs with potential therapeutic applications. With few side effects and amazing capabilities, noscapine can be considered different from other opioids-like structure compounds. Since 1930, extensive studies have been conducted in the field of pharmacological treatments from against malaria to control cough and cancer treatment. Furthermore, recent studies have shown that noscapine and some analogues, like 9-bromonoscapine, amino noscapine, and 9-nitronoscapine, can be used to treat polycystic ovaries syndrome, stroke, and other diseases. Given the numerous results presented in this field and the role of different receptors in the therapeutic effects of noscapine, we aimed to review the properties, therapeutic effects, and the role of receptors in the treatment of noscapine.

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Illicit heroin manufacturing by-products: capillary gas chromatographic determination and structural elucidation of narcotine- and norlaudanosine-related compounds

Cited by 57 publications

References 29 publications

A ‘cold synthesis’ of heroin and implications in heroin signature analysis

A ‘cold synthesis’ of heroin and implications in heroin signature analysis

A Convenient Synthesis of Aryl-Substituted N-Carbamoyl/N-Thiocarbamoyl Narcotine and Related Compounds

Biological and pharmacological activities of noscapine: Focusing on its receptors and mechanisms

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