2-[(E)-(2S,5R)-2-Isopropyl-5-methylcyclohexylidene]-N-methylhydrazine-1-carbothioamide

Oliveira, Adriano Bof de; Beck, Johannes; Daniels, Jörg; Farias, Renan Lira de

doi:10.1107/s2414314616004594

Cited by 4 publications

(13 citation statements)

References 6 publications

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“…of 0.179 (3). Selected geometric parameters for the structural description of JMTSC-1 and JMTSC-2 are given in Table 1; these are in agreement with literature data (Oliveira et al, 2016;Rocha et al, 2014).…”

Section: Compound Atom Chain Torsion Angle Atom Chain Torsion Anglesupporting

confidence: 84%

“…Finally, the structure of (-)-menthone 4-methylthiosemicarbazone (Oliveira et al, 2016) shows a non-centrosymmetric dimer, with the molecules connected by pairs of N-H� � �S interactions, also with graph-set motif R 2 2 (8). A difference in this structure is the linking of the terminal N-H bonds between the molecules through N-H� � �S interactions into a tape-like structure.…”

Section: (B)mentioning

confidence: 98%

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N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

Oliveira,

Bresolin,

Beck

et al. 2024

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The equimolar and hydrochloric acid-catalysed reaction between cis-jasmone and 4-methylthiosemicarbazide in ethanolic solution yields the title compound, C13H21N3S (common name: cis-jasmone 4-methylthiosemicarbazone). Two molecules with all atoms in general positions are present in the asymmetric unit. In one of them, the carbon chain is disordered [site occupancy ratio = 0.821 (3):0.179 (3)]. The thiosemicarbazone entities [N—N—C(=S)—N] are approximately planar, with the maximum deviation from the mean plane through the selected atoms being −0.0115 (16) Å (r.m.s.d. = 0.0078 Å) for the non-disordered molecule and 0.0052 (14) Å (r.m.s.d. = 0.0031 Å) for the disordered one. The molecules are not planar, since the jasmone groups have a chain with sp 3-hybridized carbon atoms and, in addition, the thiosemicarbazone fragments are attached to the respective carbon five-membered rings and the dihedral angles between them for each molecule amount to 8.9 (1) and 6.3 (1)°. In the crystal, the molecules are connected through pairs of N—H...S and C—H...S interactions into crystallographically independent centrosymmetric dimers, in which rings of graph-set motifs R 2 2(8) and R 2 1(7) are observed. A Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are from H...H (70.6%), H...S/S...H (16.7%), H...C/C...H (7.5%) and H...N/N...H (4.9%) interactions [considering the two crystallographically independent molecules and only the disordered atoms with the highest s.o.f. for the evaluation].

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Section: Compound Atom Chain Torsion Angle Atom Chain Torsion Anglesupporting

confidence: 84%

Section: (B)mentioning

confidence: 98%

N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

Oliveira,

Bresolin,

Beck

et al. 2024

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“…The limits of quantification (LOQ) were determined as the lowest concentration giving a response of ten times the average of the baseline noise, calculated using unfortified samples. 16 For coconut charcoal, the LOD values for the compounds ranged from 0.003 to 0.009 μg mL -1 , while the LOQ values were from 0.011 to 0.03 μg mL -1 . For the menthone-thiosemicarbazone polymer, the LOD values ranged from 0.005 to 0.014 μg mL -1 , while the LOQ values were from 0.016 to 0.043 μg mL -1 ( Table 5).…”

Section: Methods Validationmentioning

confidence: 97%

“…Menthone-thiosemicarbazone crystals were synthesized and characterized according to the methodology reported by de Oliveira et al 16 with minor modification. In a hydrochloric acid-catalyzed reaction, a mixture of (-)-menthone (10 mmol) and 4-methyl-3-thiosemicarbazide (10 mmol) in ethanol (80 mL) was refluxed for 5 h. After cooling and filtering, the compound was obtained.…”

Section: S Y N T H E S I S a N D C H A Ra C T E R I Z A T I O N O F Mmentioning

confidence: 99%

Use of Coconut Charcoal and Menthone-Thiosemicarbazone Polymer as Solid Phase Materials for the Determination of N,N-Dimethyltryptamine, Harmine, Harmaline, Harmalol, and Tetrahydroharmine in Ayahuasca Beverage by Liquid Chromatography-Tandem Mass Spectrometry

Navickiene¹,

Santos²,

Santos³

et al. 2018

J. Braz. Chem. Soc.

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An extraction method based on solid-phase extraction was developed to determine the major alkaloid components, N,N-dimethyltryptamine, harmine, harmaline, harmalol, and tetrahydroharmine, in ayahuasca using ultra-performance liquid chromatography-tandem mass spectrometry. Coconut charcoal and menthone-thiosemicarbazone polymer were tested as new adsorbent materials. Experiments carried out at levels of 1, 5, 10, 50, 100, and 250 μg mL-1 resulted in recoveries in the ranges 45.3-115.7% for menthone-thiosemicarbazone and 40.6-116.2% for coconut charcoal. The detection and quantification limits ranged from 0.003 to 0.016 μg mL-1 and from 0.009 to 0.043 μg mL-1 , respectively. The method developed was linear over the tested range (0.05-1.0 μg mL-1), with correlation coefficients ranging from 0.9969 to 0.9998. The technique was applied for analysis of the compounds in an ayahuasca sample collected from a religious group located in the city of Fortaleza, obtaining concentrations in the range from 0.3 to 19.3 mg mL-1 .

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“…The name of the first author in the paper by Oliveira et al (2023) is incorrect and should be 'Adriano Bof de Oliveira', as given above.…”

mentioning

confidence: 99%

2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide. Corrigendum

Oliveira,

Bresolin,

Beck

et al. 2024

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2-[(E)-(2S,5R)-2-Isopropyl-5-methylcyclohexylidene]-N-methylhydrazine-1-carbothioamide

Cited by 4 publications

References 6 publications

N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

Use of Coconut Charcoal and Menthone-Thiosemicarbazone Polymer as Solid Phase Materials for the Determination of N,N-Dimethyltryptamine, Harmine, Harmaline, Harmalol, and Tetrahydroharmine in Ayahuasca Beverage by Liquid Chromatography-Tandem Mass Spectrometry

2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide. Corrigendum

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