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Preparation of tertiary amines by the reaction of iminium ions derived from unsymmetrical aminals with zinc and magnesium organometallics.

Organic letters

Werner V, Ellwart M, Wagner AJ, Knochel P.
PMID: 25849577
Org Lett. 2015 Apr 17;17(8):2026-9. doi: 10.1021/acs.orglett.5b00801. Epub 2015 Apr 07.

We report a convenient one-pot preparation of polyfunctional tertiary amines, including various biorelevant phenethylamines or ephedrine derivatives, via the reaction of new functionalized iminium ions with a variety of zinc and magnesium organometallic reagents. These iminium ions were generated...

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Werner V, Ellwart M, Wagner AJ, et al. Preparation of tertiary amines by the reaction of iminium ions derived from unsymmetrical aminals with zinc and magnesium organometallics. Org Lett. 2015;17(8):2026-9doi: 10.1021/acs.orglett.5b00801.
Werner, V., Ellwart, M., Wagner, A. J., & Knochel, P. (2015). Preparation of tertiary amines by the reaction of iminium ions derived from unsymmetrical aminals with zinc and magnesium organometallics. Organic letters, 17(8), 2026-9. https://doi.org/10.1021/acs.orglett.5b00801
Werner, Veronika, et al. "Preparation of tertiary amines by the reaction of iminium ions derived from unsymmetrical aminals with zinc and magnesium organometallics." Organic letters vol. 17,8 (2015): 2026-9. doi: https://doi.org/10.1021/acs.orglett.5b00801
Werner V, Ellwart M, Wagner AJ, Knochel P. Preparation of tertiary amines by the reaction of iminium ions derived from unsymmetrical aminals with zinc and magnesium organometallics. Org Lett. 2015 Apr 17;17(8):2026-9. doi: 10.1021/acs.orglett.5b00801. Epub 2015 Apr 07. PMID: 25849577.
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A Proton-Ionizable Ester Crown of 3,5-Disubstituted 1H-Pyrazole Able To Form Stable Dinuclear Complexes with Lipophilic Phenethylamines.

The Journal of organic chemistry

Campayo L, Bueno JM, Navarro P, Ochoa C, Jimenez-Barbero J, Pèpe G, Samat A.
PMID: 11671626
J Org Chem. 1997 May 02;62(9):2684-2693. doi: 10.1021/jo9623651.

A convenient synthesis of the proton-ionizable crown 3 is reported that uses dibutyltin oxide. In acetonitrile, the reaction of 3 (LH(2)) with phenethylamine and homoveratrylamine (molar ratio 1:2) affords solid dinuclear complexes [LH(2)]2RNH(2) (4a,b), which spectroscopic (FAB-MS, IR, (1)H...

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Campayo L, Bueno JM, Navarro P, et al. A Proton-Ionizable Ester Crown of 3,5-Disubstituted 1H-Pyrazole Able To Form Stable Dinuclear Complexes with Lipophilic Phenethylamines. J Org Chem. 1997;62(9):2684-2693doi: 10.1021/jo9623651.
Campayo, L., Bueno, J. M., Navarro, P., Ochoa, C., Jimenez-Barbero, J., Pèpe, G., & Samat, A. (1997). A Proton-Ionizable Ester Crown of 3,5-Disubstituted 1H-Pyrazole Able To Form Stable Dinuclear Complexes with Lipophilic Phenethylamines. The Journal of organic chemistry, 62(9), 2684-2693. https://doi.org/10.1021/jo9623651
Campayo, Lucrecia, et al. "A Proton-Ionizable Ester Crown of 3,5-Disubstituted 1H-Pyrazole Able To Form Stable Dinuclear Complexes with Lipophilic Phenethylamines." The Journal of organic chemistry vol. 62,9 (1997): 2684-2693. doi: https://doi.org/10.1021/jo9623651
Campayo L, Bueno JM, Navarro P, Ochoa C, Jimenez-Barbero J, Pèpe G, Samat A. A Proton-Ionizable Ester Crown of 3,5-Disubstituted 1H-Pyrazole Able To Form Stable Dinuclear Complexes with Lipophilic Phenethylamines. J Org Chem. 1997 May 02;62(9):2684-2693. doi: 10.1021/jo9623651. PMID: 11671626.
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Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions.

Organic letters

Nakamura S, Tanaka M, Taniguchi T, Uchiyama M, Ohwada T.
PMID: 12790535
Org Lett. 2003 Jun 12;5(12):2087-90. doi: 10.1021/ol034526a.

[reaction: see text] High stereoselectivities were found in a wide range of superacid-catalyzed Pictet-Spengler cyclization reactions. Particularly in the cases of 2-alkyl-N-benzylidene-2-phenethylamines, an enhanced stereoselectivity was observed under the superacid conditions as compared with the corresponding weak acid (TFA)-catalyzed...

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Nakamura S, Tanaka M, Taniguchi T, et al. Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions. Org Lett. 2003;5(12):2087-90doi: 10.1021/ol034526a.
Nakamura, S., Tanaka, M., Taniguchi, T., Uchiyama, M., & Ohwada, T. (2003). Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions. Organic letters, 5(12), 2087-90. https://doi.org/10.1021/ol034526a
Nakamura, Satoshi, et al. "Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions." Organic letters vol. 5,12 (2003): 2087-90. doi: https://doi.org/10.1021/ol034526a
Nakamura S, Tanaka M, Taniguchi T, Uchiyama M, Ohwada T. Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions. Org Lett. 2003 Jun 12;5(12):2087-90. doi: 10.1021/ol034526a. PMID: 12790535.
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A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.

Talanta

Chen BH, Liu JT, Chen WX, Chen HM, Lin CH.
PMID: 18371669
Talanta. 2008 Jan 15;74(4):512-7. doi: 10.1016/j.talanta.2007.06.012. Epub 2007 Jun 19.

Certain characteristic fragmentations of tryptamines (indoleethylamine) and phenethylamines are described. Based on the GC-EI/MS, LC-ESI/MS and MALDI/TOFMS, the mass fragmentations of 13 standard compounds, including alpha-methyltryptamine (AMT), N,N-dimethyltryptamine (DMT), 5-methoxy-alpha-methyltryptamine (5-MeO-AMT), N,N-diethyltryptamine (DET), N,N-dipropyltryptamine (DPT), N,N-dibutyltryptamine (DBT), N,N-diisopropyltryptamine (DIPT),...

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Chen BH, Liu JT, Chen WX, et al. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta. 2007;74(4):512-7doi: 10.1016/j.talanta.2007.06.012.
Chen, B. H., Liu, J. T., Chen, W. X., Chen, H. M., & Lin, C. H. (2008). A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 74(4), 512-7. https://doi.org/10.1016/j.talanta.2007.06.012
Chen, Bo-Hong, et al. "A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation." Talanta vol. 74,4 (2008): 512-7. doi: https://doi.org/10.1016/j.talanta.2007.06.012
Chen BH, Liu JT, Chen WX, Chen HM, Lin CH. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta. 2008 Jan 15;74(4):512-7. doi: 10.1016/j.talanta.2007.06.012. Epub 2007 Jun 19. PMID: 18371669.
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Cytokinin antagonist activity of substituted phenethylamines in plant cell culture.

Plant physiology

Christou P, Barton KA.
PMID: 16666583
Plant Physiol. 1989 Feb;89(2):564-8. doi: 10.1104/pp.89.2.564.

A series of structurally related substituted phenethylamines shows extreme toxicity toward wild-type callus tissue cultures of tobacco (Nicotiana tabacum), soybean (Glycine max), corn (Zea mays), and sunflower (Helianthus annuus L.), but tobacco crown gall cultures are resistant to the...

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Christou P, Barton KA. Cytokinin antagonist activity of substituted phenethylamines in plant cell culture. Plant Physiol. 1989;89(2):564-8doi: 10.1104/pp.89.2.564.
Christou, P., & Barton, K. A. (1989). Cytokinin antagonist activity of substituted phenethylamines in plant cell culture. Plant physiology, 89(2), 564-8. https://doi.org/10.1104/pp.89.2.564
Christou, P, and Barton, K A. "Cytokinin antagonist activity of substituted phenethylamines in plant cell culture." Plant physiology vol. 89,2 (1989): 564-8. doi: https://doi.org/10.1104/pp.89.2.564
Christou P, Barton KA. Cytokinin antagonist activity of substituted phenethylamines in plant cell culture. Plant Physiol. 1989 Feb;89(2):564-8. doi: 10.1104/pp.89.2.564. PMID: 16666583; PMCID: PMC1055882.
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Determination of active ingredients in cough-cold preparations by micellar liquid chromatography.

Talanta

Gil-Agustí M, Monferrer-Pons L, García-Alvarez-Coque MC, Esteve-Romero J.
PMID: 18968285
Talanta. 2001 May 30;54(4):621-30. doi: 10.1016/s0039-9140(01)00315-0.

The chromatographic behaviour of some active ingredients in cough-cold pharmaceutical preparations, the antihistamine chlorpheniramine (or the dextro enantiomer dexchlorpheniramine), and the phenethylamines phenylephrine, phenylpropanolamine and pseudoephedrine, has been studied using a C(18) column, micellar mobile phases of sodium dodecyl...

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Gil-Agustí M, Monferrer-Pons L, García-Alvarez-Coque MC, et al. Determination of active ingredients in cough-cold preparations by micellar liquid chromatography. Talanta. 2001;54(4):621-30doi: 10.1016/s0039-9140(01)00315-0.
Gil-Agustí, M., Monferrer-Pons, L., García-Alvarez-Coque, M. C., & Esteve-Romero, J. (2001). Determination of active ingredients in cough-cold preparations by micellar liquid chromatography. Talanta, 54(4), 621-30. https://doi.org/10.1016/s0039-9140(01)00315-0
Gil-Agustí, M, et al. "Determination of active ingredients in cough-cold preparations by micellar liquid chromatography." Talanta vol. 54,4 (2001): 621-30. doi: https://doi.org/10.1016/s0039-9140(01)00315-0
Gil-Agustí M, Monferrer-Pons L, García-Alvarez-Coque MC, Esteve-Romero J. Determination of active ingredients in cough-cold preparations by micellar liquid chromatography. Talanta. 2001 May 30;54(4):621-30. doi: 10.1016/s0039-9140(01)00315-0. PMID: 18968285.
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Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa.

Planta medica

Prakash A, Varma RK, Ghosal S.
PMID: 17402065
Planta Med. 1981 Dec;43(4):384-8. doi: 10.1055/s-2007-971529.

Three types of alkaloidal constituents, viz., beta-phenethylamines, quinazolines and carboxylated tryptamines, in addition to choline and betaine have been isolated from Sida acuta Burm., S. humilis Willd., S. rhombifolia L., and S. spinosa L. and characterized by their physical...

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Prakash A, Varma RK, Ghosal S. Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta Med. 1981;43(4):384-8doi: 10.1055/s-2007-971529.
Prakash, A., Varma, R. K., & Ghosal, S. (1981). Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta medica, 43(4), 384-8. https://doi.org/10.1055/s-2007-971529
Prakash, A, et al. "Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa." Planta medica vol. 43,4 (1981): 384-8. doi: https://doi.org/10.1055/s-2007-971529
Prakash A, Varma RK, Ghosal S. Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta Med. 1981 Dec;43(4):384-8. doi: 10.1055/s-2007-971529. PMID: 17402065.
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25I-NBOMe, a phenethylamine derivative, induces adverse cardiovascular effects in rodents: possible involvement of p21 (CDC42/RAC)-activated kinase 1.

Drug and chemical toxicology

Yoon KS, Gu SM, Cha HJ, Kim YH, Yun J, Lee JM.
PMID: 32597268
Drug Chem Toxicol. 2020 Jun 29;1-9. doi: 10.1080/01480545.2020.1784924. Epub 2020 Jun 29.

Abuse of new psychoactive substances is an emerging social problem. Several phenethylamines are internationally controlled substances as they are likely to be abused and have adverse effects. Phenethylamine analog 2-(4-iodo-2,5-dimethoxyphenyl)-

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Yoon KS, Gu SM, Cha HJ, et al. 25I-NBOMe, a phenethylamine derivative, induces adverse cardiovascular effects in rodents: possible involvement of p21 (CDC42/RAC)-activated kinase 1. Drug Chem Toxicol. 2020;1-9doi: 10.1080/01480545.2020.1784924.
Yoon, K. S., Gu, S. M., Cha, H. J., Kim, Y. H., Yun, J., & Lee, J. M. (2020). 25I-NBOMe, a phenethylamine derivative, induces adverse cardiovascular effects in rodents: possible involvement of p21 (CDC42/RAC)-activated kinase 1. Drug and chemical toxicology, 1-9. https://doi.org/10.1080/01480545.2020.1784924
Yoon, Kyung Sik, et al. "25I-NBOMe, a phenethylamine derivative, induces adverse cardiovascular effects in rodents: possible involvement of p21 (CDC42/RAC)-activated kinase 1." Drug and chemical toxicology vol. (2020): 1-9. doi: https://doi.org/10.1080/01480545.2020.1784924
Yoon KS, Gu SM, Cha HJ, Kim YH, Yun J, Lee JM. 25I-NBOMe, a phenethylamine derivative, induces adverse cardiovascular effects in rodents: possible involvement of p21 (CDC42/RAC)-activated kinase 1. Drug Chem Toxicol. 2020 Jun 29;1-9. doi: 10.1080/01480545.2020.1784924. Epub 2020 Jun 29. PMID: 32597268.
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NBOMes-Highly Potent and Toxic Alternatives of LSD.

Frontiers in neuroscience

Zawilska JB, Kacela M, Adamowicz P.
PMID: 32174803
Front Neurosci. 2020 Feb 26;14:78. doi: 10.3389/fnins.2020.00078. eCollection 2020.

Recently, a new class of psychedelic compounds named NBOMe (or 25X-NBOMe) has appeared on the illegal drug market. NBOMes are analogs of the 2C family of phenethylamine drugs, originally synthesized by Alexander Shulgin, that contain a

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Zawilska JB, Kacela M, Adamowicz P. NBOMes-Highly Potent and Toxic Alternatives of LSD. Front Neurosci. 2020;14:78doi: 10.3389/fnins.2020.00078.
Zawilska, J. B., Kacela, M., & Adamowicz, P. (2020). NBOMes-Highly Potent and Toxic Alternatives of LSD. Frontiers in neuroscience, 1478. https://doi.org/10.3389/fnins.2020.00078
Zawilska, Jolanta B, et al. "NBOMes-Highly Potent and Toxic Alternatives of LSD." Frontiers in neuroscience vol. 14 (2020): 78. doi: https://doi.org/10.3389/fnins.2020.00078
Zawilska JB, Kacela M, Adamowicz P. NBOMes-Highly Potent and Toxic Alternatives of LSD. Front Neurosci. 2020 Feb 26;14:78. doi: 10.3389/fnins.2020.00078. eCollection 2020. PMID: 32174803; PMCID: PMC7054380.
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Rapid detection of .

Forensic toxicology

Sugie KI, Kurakami D, Akutsu M, Saito K.
PMID: 29963202
Forensic Toxicol. 2018;36(2):261-269. doi: 10.1007/s11419-017-0400-y. Epub 2018 Jan 12.

PURPOSE: Phenethylamines constitute the majority of drug-related arrests in Japan. Recently, the smuggling of METHODS: In this study, a rapid and accurate method for the detection of RESULTS: During GC-MS analysis of CONCLUSIONS: Hence, DART-TOF-MS provides a rapid and...

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Sugie KI, Kurakami D, Akutsu M, et al. Rapid detection of . Forensic Toxicol. 2018;36(2):261-269doi: 10.1007/s11419-017-0400-y.
Sugie, K. I., Kurakami, D., Akutsu, M., & Saito, K. (2018). Rapid detection of . Forensic toxicology, 36(2), 261-269. https://doi.org/10.1007/s11419-017-0400-y
Sugie, Ken-Ichi, et al. "Rapid detection of ." Forensic toxicology vol. 36,2 (2018): 261-269. doi: https://doi.org/10.1007/s11419-017-0400-y
Sugie KI, Kurakami D, Akutsu M, Saito K. Rapid detection of . Forensic Toxicol. 2018;36(2):261-269. doi: 10.1007/s11419-017-0400-y. Epub 2018 Jan 12. PMID: 29963202; PMCID: PMC6002434.
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Discrete Derivatives for Atom-Pairs as a Novel Graph-Theoretical Invariant for Generating New Molecular Descriptors: Orthogonality, Interpretation and QSARs/QSPRs on Benchmark Databases.

Molecular informatics

Martínez-Santiago O, Millán-Cabrera R, Marrero-Ponce Y, Barigye SJ, Martínez-López Y, Torrens F, Pérez-Giménez F.
PMID: 27485891
Mol Inform. 2014 May;33(5):343-68. doi: 10.1002/minf.201300173. Epub 2014 May 12.

This report presents a new mathematical method based on the concept of the derivative of a molecular graph (G) with respect to a given event (S) to codify chemical structure information. The derivate over each pair of atoms in...

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Martínez-Santiago O, Millán-Cabrera R, Marrero-Ponce Y, et al. Discrete Derivatives for Atom-Pairs as a Novel Graph-Theoretical Invariant for Generating New Molecular Descriptors: Orthogonality, Interpretation and QSARs/QSPRs on Benchmark Databases. Mol Inform. 2014;33(5):343-68doi: 10.1002/minf.201300173.
Martínez-Santiago, O., Millán-Cabrera, R., Marrero-Ponce, Y., Barigye, S. J., Martínez-López, Y., Torrens, F., & Pérez-Giménez, F. (2014). Discrete Derivatives for Atom-Pairs as a Novel Graph-Theoretical Invariant for Generating New Molecular Descriptors: Orthogonality, Interpretation and QSARs/QSPRs on Benchmark Databases. Molecular informatics, 33(5), 343-68. https://doi.org/10.1002/minf.201300173
Martínez-Santiago, Oscar, et al. "Discrete Derivatives for Atom-Pairs as a Novel Graph-Theoretical Invariant for Generating New Molecular Descriptors: Orthogonality, Interpretation and QSARs/QSPRs on Benchmark Databases." Molecular informatics vol. 33,5 (2014): 343-68. doi: https://doi.org/10.1002/minf.201300173
Martínez-Santiago O, Millán-Cabrera R, Marrero-Ponce Y, Barigye SJ, Martínez-López Y, Torrens F, Pérez-Giménez F. Discrete Derivatives for Atom-Pairs as a Novel Graph-Theoretical Invariant for Generating New Molecular Descriptors: Orthogonality, Interpretation and QSARs/QSPRs on Benchmark Databases. Mol Inform. 2014 May;33(5):343-68. doi: 10.1002/minf.201300173. Epub 2014 May 12. PMID: 27485891.
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Analytical Validation of a Portable Mass Spectrometer Featuring Interchangeable, Ambient Ionization Sources for High Throughput Forensic Evidence Screening.

Journal of the American Society for Mass Spectrometry

Lawton ZE, Traub A, Fatigante WL, Mancias J, O'Leary AE, Hall SE, Wieland JR, Oberacher H, Gizzi MC, Mulligan CC.
PMID: 28000107
J Am Soc Mass Spectrom. 2017 Jun;28(6):1048-1059. doi: 10.1007/s13361-016-1562-2. Epub 2016 Dec 20.

Forensic evidentiary backlogs are indicative of the growing need for cost-effective, high-throughput instrumental methods. One such emerging technology that shows high promise in meeting this demand while also allowing on-site forensic investigation is portable mass spectrometric (MS) instrumentation, particularly...

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Lawton ZE, Traub A, Fatigante WL, et al. Analytical Validation of a Portable Mass Spectrometer Featuring Interchangeable, Ambient Ionization Sources for High Throughput Forensic Evidence Screening. J Am Soc Mass Spectrom. 2016;28(6):1048-1059doi: 10.1007/s13361-016-1562-2.
Lawton, Z. E., Traub, A., Fatigante, W. L., Mancias, J., O'Leary, A. E., Hall, S. E., Wieland, J. R., Oberacher, H., Gizzi, M. C., & Mulligan, C. C. (2017). Analytical Validation of a Portable Mass Spectrometer Featuring Interchangeable, Ambient Ionization Sources for High Throughput Forensic Evidence Screening. Journal of the American Society for Mass Spectrometry, 28(6), 1048-1059. https://doi.org/10.1007/s13361-016-1562-2
Lawton, Zachary E, et al. "Analytical Validation of a Portable Mass Spectrometer Featuring Interchangeable, Ambient Ionization Sources for High Throughput Forensic Evidence Screening." Journal of the American Society for Mass Spectrometry vol. 28,6 (2017): 1048-1059. doi: https://doi.org/10.1007/s13361-016-1562-2
Lawton ZE, Traub A, Fatigante WL, Mancias J, O'Leary AE, Hall SE, Wieland JR, Oberacher H, Gizzi MC, Mulligan CC. Analytical Validation of a Portable Mass Spectrometer Featuring Interchangeable, Ambient Ionization Sources for High Throughput Forensic Evidence Screening. J Am Soc Mass Spectrom. 2017 Jun;28(6):1048-1059. doi: 10.1007/s13361-016-1562-2. Epub 2016 Dec 20. PMID: 28000107.
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Showing 1 to 12 of 60 entries