2-phenylpropan-2-amine (cumylamine) [CAS 585-32-0; InChIKey KDFDOINBXBEOLZ-UHFFFAOYSA-N; Reaxys, Sub

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NH 2

7 substances in Re2016-02-17 07h:05m:43s (EST) axys

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Reaxys ID 774150 View in Reaxys

1/7 CAS Registry Number: 585-32-0 Chemical Name: 2-phenyl-2-propylamine; Cumylamine Linear Structure Formula: C6H5C(CH3)2NH2 Molecular Formula: C9H13N Molecular Weight: 135.209 Type of Substance: isocyclic InChI Key: KDFDOINBXBEOLZ-UHFFFAOYSA-N Note:

NH 2

Substance Label (28) Label References 4

Clayden, Jonathan; Knowles, Faye E.; Baldwin, Ian R.; Journal of the American Chemical Society; vol. 127; nb. 8; (2005); p. 2412 - 2413, View in Reaxys; Ruiz-Castillo, Paula; Blackmond, Donna G.; Buchwald, Stephen L.; Journal of the American Chemical Society; vol. 137; nb. 8; (2015); p. 3085 - 3092, View in Reaxys

28b

Jaudzems, Kristaps; Tars, Kaspars; Maurops, Gundars; Ivdra, Natalija; Otikovs, Martins; Leitans, Janis; Kanepe-Lapsa, Iveta; Domraceva, Ilona; Mutule, Ilze; Trapencieris, Peteris; Blackman, Michael J.; Jirgensons, Aigars; ACS Medicinal Chemistry Letters; vol. 5; nb. 4; (2014); p. 373 - 377, View in Reaxys

1a

Suzuki, Chiharu; Morimoto, Keisuke; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; Advanced Synthesis and Catalysis; vol. 356; nb. 7; (2014); p. 1521 - 1526, View in Reaxys

2f

Nguyen, Thanh Binh; Ermolenko, Ludmila; Al-Mourabit, Ali; Synthesis (Germany); vol. 46; nb. 23; (2014); p. 3172 - 3179, View in Reaxys

5b

Rodrguez, Aleix; Albert, Joan; Ariza, Xavier; Garcia, Jordi; Granell, Jaume; Farrs, Jaume; La Mela, Andrea; Nicols, Ernesto; Journal of Organic Chemistry; vol. 79; nb. 20; (2014); p. 9578 - 9585, View in Reaxys

5

Clayden, Jonathan; Tchabanenko, Kirill; Chemical Communications; nb. 4; (2000); p. 317 - 318, View in Reaxys; Hansen, Stephanie R.; Spangler, Jillian E.; Hansen, Jorn H.; Davies, Huw M.L.; Organic Letters; vol. 14; nb. 17; (2012); p. 4626 - 4629, View in Reaxys; Suzuki, Chiharu; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; Organic Letters; vol. 15; nb. 15; (2013); p. 3990 - 3993, View in Reaxys

36g

Zhao, Huiping; Blagg, Brian S.J.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 2; (2013); p. 552 - 557, View in Reaxys

32

Gorla, Suresh Kumar; Kavitha, Mandapati; Zhang, Minjia; Liu, Xiaoping; Sharling, Lisa; Gollapalli, Deviprasad R.; Striepen, Boris; Hedstrom, Lizbeth; Cuny, Gregory D.; Journal of Medicinal Chemistry; vol.

55; nb. 17; (2012); p. 7759 - 7771, View in Reaxys

12e

Tomashenko, Olesya; Sokolov, Viktor; Tomashevskiy, Alexander; De Meijere, Armin; Synlett; nb. 4; (2007); p. 652 - 654, View in Reaxys

PhC(CH3)2NH2

Luisi, Renzo; Capriati, Vito; Di Cunto, Peppino; Florio, Saverio; Mansueto, Rosmara; Organic Letters; vol. 9; nb. 17; (2007); p. 3295 - 3298, View in Reaxys

13d

Ikeda, Hiroshi; Hoshi, Yosuke; Namai, Hayato; Tanaka, Futoshi; Goodman, Joshua L.; Mizuno, Kazuhiko; Chemistry - A European Journal; vol. 13; nb. 33; (2007); p. 9207 - 9215, View in Reaxys

6

Kondo, Kazuhiro; Murakami, Yasuoki; Chemical and Pharmaceutical Bulletin; vol. 46; nb. 8; (1998); p. 1217 - 1219, View in Reaxys; Shao, Ning; Wang, Cheng; Huang, Xianhai; Xiao, Dong; Palani, Anandan; Aslanian, Robert; Shih, Neng-Yang; Tetrahedron Letters; vol. 47; nb. 38; (2006); p. 6743 - 6746, View in Reaxys

1k

Herve, Gregoire; Jacob, Guy; Gallo, Roger; Chemistry - A European Journal; vol. 12; nb. 12; (2006); p. 3339 - 3344, View in Reaxys

cumylamine

Liu, Wei-Jun; Chen, Zhen-Liang; Chen, Zhi-Yong; Hu, Wen-Hao; Tetrahedron Asymmetry; vol. 16; nb. 9; (2005); p. 1693 - 1698, View in Reaxys

PhMe2CNH2

Sano, Tomohumi; Takagi, Toshiyuki; Gama, Yasuo; Shibuya, Isao; Shimizu, Masao; Synthesis; nb. 10; (2004); p. 1585 - 1588, View in Reaxys

P&2%'-a

Abdel-Rahman, Hamdy M.; El-Koussi, Nawal A.; Alkaramany, Gamal S.; Youssef, Adel F.; Kiso, Yoshiaki; Archiv der Pharmazie; vol. 337; nb. 11; (2004); p. 587 - 598, View in Reaxys

Table 1, entry 1

Crosignani, Stefano; Gonzalez, Jerome; Swinnen, Dominique; Organic Letters; vol. 6; nb. 24; (2004); p.

4579 - 4582, View in Reaxys

7

Huang, Xianhai; Palani, Anandan; Xiao, Dong; Aslanian, Robert; Shih, Neng-Yang; Organic Letters; vol.

6; nb. 25; (2004); p. 4795 - 4798, View in Reaxys

amine to 2m

Shimizu, Masao; Takeda, Ayanobu; Fukazawa, Hidenori; Abe, Yoshimoto; Shibuya, Isao; Heterocycles; vol. 60; nb. 8; (2003); p. 1855 - 1864, View in Reaxys

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2

Clayden, Jonathan; Menet, Christel J; Tchabanenko, Kirill; Tetrahedron; vol. 58; nb. 23; (2002); p. 4727 4733, View in Reaxys

amine, 5

Lake, Fredrik; Moberg, Christina; European Journal of Organic Chemistry; nb. 18; (2002); p. 3179 - 3188, View in Reaxys

8

Engel; Pan; Ying; Alemany; Journal of the American Chemical Society; vol. 123; nb. 16; (2001); p. 3706 3715, View in Reaxys

21

Kondo, Kazuhiro; Sekimoto, Erika; Nakao, Junko; Murakami, Yasuoki; Tetrahedron; vol. 56; nb. 32; (2000); p. 5843 - 5856, View in Reaxys

6a

Sagawa, Shoichi; Abe, Hiroyuki; Hase, Yasunori; Inaba, Takashi; Journal of Organic Chemistry; vol. 64; nb. 13; (1999); p. 4962 - 4965, View in Reaxys

11o

Giardina, Giuseppe A. M.; Raveglia, Luca F.; Grugni, Mario; Sarau, Henry M.; Farina, Carlo; Medhurst, Andrew D.; Graziani, Davide; Schmidt, Dulcie B.; Rigolio, Roberto; Luttmann, Mark; Cavagnera, Stefano; Foley, James J.; Vecchietti, Vittorio; Hay, Douglas W. P.; Journal of Medicinal Chemistry; vol. 42; nb. 6; (1999); p. 1053 - 1065, View in Reaxys

3

Chan-Shing, Elisa Soazara; Boucher, Denys; Lessard, Jean; Canadian Journal of Chemistry; vol. 77; nb.

5-6; (1999); p. 687 - 694, View in Reaxys

amine e

Deyrup; Nowicki; Richards; Otero; Harrison; Baker; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 359; nb. 3; (1999); p. 168 - 177, View in Reaxys

PA

Sapronov, N. S.; Eliseev, V. V.; Torkunov, P. A.; Krylova, I. B.; Evdokimova, N. R.; Pharmaceutical Chemistry Journal; vol. 32; nb. 11; (1998); p. 575 - 577; Khimiko-Farmatsevticheskii Zhurnal; vol. 32; nb. 11; (1998); p. 9 - 11, View in Reaxys

Patent-Specific Data (5) Location in Patent References Page/Page column

Patent; Nippon Soda Co., Ltd.; FURUKAWA Hironori; NAKAMURA Takehiko; TAMAI Tetsuo; HANAI Daisuke; EP2628724; (2013); (A1) English, View in Reaxys Patent; Pathway Therapeutics Inc.; US2012/252802; (2012); (A1) English, View in Reaxys Patent; BAYER HEALTHCARE AG; US2009/312381; (2009); (A1) English, View in Reaxys Patent; BIOVITRUM AB (PUBL); WO2009/147216; (2009); (A1) English, View in Reaxys Patent; ASTRAZENECA AB; WO2004/41784; (2004); (A1) English, View in Reaxys

Boiling Point (15) Boiling Point [°C] Pressure (Boiling Point) [Torr]

Location

References

supporting information

Schneider, Cedric; Broda, Ellen; Snieckus, Victor; Organic Letters; vol. 13; nb. 14; (2011); p. 3588 - 3591, View in Reaxys

98

20

98

20

Blanchet, Jerome; Macklin, Todd; Ang, Patrick; Metallinos, Costa; Snieckus, Victor; Journal of Organic Chemistry; vol. 72; nb. 9; (2007); p. 3199 - 3206, View in Reaxys

92 - 93

26

Kornblum, Nathan; Fifolt, Michael J.; Tetrahedron; vol. 45; nb. 5; (1989); p. 1311 - 1322, View in Reaxys

81 - 82

10

Timberlake, Jack W.; Alender, Jeff; Garner, Archie W.; Hodges, Melvin L.; Oezmeral, Cenan; et al.; Journal of Organic Chemistry; vol. 46; nb. 10; (1981); p. 2082 - 2089, View in Reaxys

45

1

Leffler, J. E.; Zupancic, J. J.; Journal of the American Chemical Society; vol. 102; nb. 1; (1980); p. 259 - 267, View in Reaxys

100

22

Balderman,D.; Kalir,A.; Synthesis; (1978); p. 24 - 26, View in Reaxys

94

26

Kornblum,N. et al.; Journal of Organic Chemistry; vol. 43; nb. 7; (1978); p. 1394 - 1399, View in Reaxys

70 - 73

8

Davis,F.A.; Mancinelli,P.A.; Journal of Organic Chemistry; vol. 42; nb. 2; (1977); p. 398 - 399, View in Reaxys

196 - 197

762

Abramovitch,R.A.; Kyba,E.P.; Journal of the American Chemical Society; vol. 96; (1974); p. 480 - 488, View in Reaxys; Brander; Recueil des Travaux Chimiques des Pays-Bas; vol. 37; (1918); p. 83, View in Reaxys

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98

11

Duismann,W.; Ruechardt,C.; Chemische Berichte; vol. 106; (1973); p. 1083 - 1098, View in Reaxys

63 - 64

1

Lindberg et al.; Acta Pharmaceutica Suecica; vol. 6; (1969); p.

617,620, View in Reaxys

62 - 64

5

Kovacic,P. et al.; Journal of Organic Chemistry; vol. 33; (1968); p.

4515 - 4520, View in Reaxys

72 - 73

8

Cope; Foster; Towle; Journal of the American Chemical Society; vol. 71; (1949); p. 3929,3933, View in Reaxys

94 - 95

22

Baker; Ingold; Journal of the Chemical Society; (1927); p. 262, View in Reaxys

194 - 195.5

754.5

Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33, View in Reaxys

Refractive Index (5) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Re- References fractive Index) [°C]

1.5174

589

24

Kornblum,N. et al.; Journal of Organic Chemistry; vol. 43; nb. 7; (1978); p. 1394 - 1399, View in Reaxys; Kornblum, Nathan; Fifolt, Michael J.; Tetrahedron; vol. 45; nb. 5; (1989); p. 1311 - 1322, View in Reaxys

1.525

589

16

Balderman,D.; Kalir,A.; Synthesis; (1978); p. 24 - 26, View in Reaxys

1.5185

589

25

Lindberg et al.; Acta Pharmaceutica Suecica; vol. 6; (1969); p.

617,620, View in Reaxys

1.5175 - 1.5185

589

25

Cope; Foster; Towle; Journal of the American Chemical Society; vol. 71; (1949); p. 3929,3933, View in Reaxys

1.5181

589

25

Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33, View in Reaxys

Density (2) 1 of 2

Density [g·cm-3]

0.956

Reference Temperature [°C]

0

Measurement Tempera- 0 ture [°C] Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33, View in Reaxys 2 of 2

Density [g·cm-3]

0.9424

Reference Temperature [°C]

0

Measurement Tempera- 20 ture [°C] Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33, View in Reaxys Crystal Property Description (3) Colour & Other Location Properties

References

yellow

Paragraph 0043

Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys

yellow

supporting information

Schneider, Cedric; Broda, Ellen; Snieckus, Victor; Organic Letters; vol. 13; nb. 14; (2011); p. 3588 - 3591, View in Reaxys

yellow

Blanchet, Jerome; Macklin, Todd; Ang, Patrick; Metallinos, Costa; Snieckus, Victor; Journal of Organic Chemistry; vol. 72; nb. 9; (2007); p. 3199 - 3206, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Dissociation Exponent (1) 1 of 1

Dissociation Exponent (pK)

10.38

Temperature (Dissociation Exponent) [°C]

20

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a/thermodynamic

Girault-Vexlearschi; Bulletin de la Societe Chimique de France; (1956); p. 589,596, View in Reaxys Enthalpy of Formation (1) Enthalpy of ForTemperature (En- Pressure (Enthalmation [Jmol-1] thalpy of Formapy of Formation) tion) [°C] [Torr] 22100

25

750.06

References

Verevkin, Sergey P.; Journal of Chemical and Engineering Data; vol. 44; nb. 6; (1999); p. 1245 - 1251, View in Reaxys

Enthalpy of Vaporization (1) Enthalpy of VaTemperature (En- References porization thalpy of Vapori[Jmol-1] zation) [°C] 56710

25

Verevkin, Sergey P.; Journal of Chemical and Engineering Data; vol. 44; nb. 6; (1999); p.

1245 - 1251, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Nelsen; Bartlett; Journal of the American Chemical Society; vol. 88; (1966); p. 143,148, View in Reaxys

NMR Spectroscopy (8) 1 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H

Location

Paragraph 0043

NMR (400 MHz, CDCl3) δ 7.54-7.48 (m, 2H), 7.34 (t, J= 7.6 Hz, 2H), 7.22 (t, J= 7.6 Hz, 1H), 1.60 (br, 2H), 1.50 (s, 6H)

Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys 2 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C

Location

Paragraph 0043

NMR (100 MHz, CDCl3) δ 150.18, 128.16, 126.14, 124.57, 52.35, 32.69

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Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English, View in Reaxys 3 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Schneider, Cedric; Broda, Ellen; Snieckus, Victor; Organic Letters; vol. 13; nb. 14; (2011); p. 3588 - 3591, View in Reaxys 4 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Chan-Shing, Elisa Soazara; Boucher, Denys; Lessard, Jean; Canadian Journal of Chemistry; vol. 77; nb. 5-6; (1999); p. 687 - 694, View in Reaxys; Blanchet, Jerome; Macklin, Todd; Ang, Patrick; Metallinos, Costa; Snieckus, Victor; Journal of Organic Chemistry; vol. 72; nb. 9; (2007); p. 3199 - 3206, View in Reaxys 5 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Ikeda, Hiroshi; Hoshi, Yosuke; Namai, Hayato; Tanaka, Futoshi; Goodman, Joshua L.; Mizuno, Kazuhiko; Chemistry - A European Journal; vol. 13; nb. 33; (2007); p. 9207 - 9215, View in Reaxys 6 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Kornblum, Nathan; Fifolt, Michael J.; Tetrahedron; vol. 45; nb. 5; (1989); p. 1311 - 1322, View in Reaxys; Kamer, Paul C. J.; Nolte, Roeland J. M.; Drenth, Wiendelt; Journal of the American Chemical Society; vol. 110; nb. 20; (1988); p. 6818 - 6825, View in Reaxys; Sato, Kazuo; Honma, Toyokuni; Sugai, Soji; Agricultural and Biological Chemistry; vol. 49; nb. 12; (1985); p. 3563 - 3568, View in Reaxys; Engel; Pan; Ying; Alemany; Journal of the American Chemical Society; vol. 123; nb. 16; (2001); p. 3706 - 3715, View in Reaxys 7 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Engel; Pan; Ying; Alemany; Journal of the American Chemical Society; vol. 123; nb. 16; (2001); p. 3706 - 3715, View in Reaxys

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8 of 8

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Kornblum,N. et al.; Journal of Organic Chemistry; vol. 43; nb. 7; (1978); p. 1394 - 1399, View in Reaxys; Balderman,D.; Kalir,A.; Synthesis; (1978); p. 24 - 26, View in Reaxys IR Spectroscopy (6) 1 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Chan-Shing, Elisa Soazara; Boucher, Denys; Lessard, Jean; Canadian Journal of Chemistry; vol. 77; nb. 5-6; (1999); p. 687 - 694, View in Reaxys 2 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3356 - 3257 cm**(-1)

Kornblum, Nathan; Fifolt, Michael J.; Tetrahedron; vol. 45; nb. 5; (1989); p. 1311 - 1322, View in Reaxys 3 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3350 - 3275 cm**(-1)

Kamer, Paul C. J.; Nolte, Roeland J. M.; Drenth, Wiendelt; Journal of the American Chemical Society; vol. 110; nb.

20; (1988); p. 6818 - 6825, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Bands

Kornblum,N. et al.; Journal of Organic Chemistry; vol. 43; nb. 7; (1978); p. 1394 - 1399, View in Reaxys 5 of 6

Description (IR Spectroscopy)

IR

Abramovitch,R.A.; Kyba,E.P.; Journal of the American Chemical Society; vol. 96; (1974); p. 480 - 488, View in Reaxys 6 of 6

Description (IR Spectroscopy)

Spectrum

Leysen; van Rysselberge; Spectrochimica Acta; vol. 19; (1963); p. 243,246, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Duismann,W.; Ruechardt,C.; Chemische Berichte; vol. 106; (1973); p. 1083 - 1098, View in Reaxys; Patent; Sumitomo Chemical Company, Limited; US4274862; (1981); (A1) English, View in Reaxys; Vaughan,W.R.; Carlson,R.D.; Journal of the American Chemical Society; vol. 84; (1962); p. 769 - 774, View in Reaxys; Abramovitch,R.A.; Kyba,E.P.; Journal of the American Chemical Society; vol. 96; (1974); p. 480 - 488, View in Reaxys; Patent; Sankyo Company, Limited; US5302621; (1994); (A1) English, View in Reaxys; Klamann,D. et al.; Justus Liebigs Annalen der Chemie; vol. 686; (1965); p. 122 - 133, View in Reaxys; Collin,G. et al.; Justus Liebigs Annalen der Chemie; vol. 702; (1967); p. 55 - 67, View in Reaxys; Walter,W.; Randau,G.; Justus Liebigs Annalen der Chemie; vol. 722; (1969); p. 52 - 79, View in Reaxys; Patent; Cytec Technology Corp.; US5840908; (1998); (A1) English, View in Reaxys; Christol,H. et al.; Bulletin de la Societe Chimique de France; (1961); p. 2319 - 2324, View in Reaxys; Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US5006157; (1991); (A1) English, View in Reaxys; Patent; Novo Nordisk A/S; US6329367; (2001); (B1) English, View in Reaxys; Patent; Sankyo Company, Limited; US6329405; (2001); (B1) English, View in Reaxys; Patent; American Home Products Corporation; US5466712; (1995); (A1) English, View in Reaxys; Patent; Yoshitomi Pharmaceutical Industries, Ltd.; US5478838; (1995); (A1) English, View in Reaxys; Patent; Sankyo Company, Limited; US5536714; (1996); (A1) English, View in Reaxys; Patent; Mitsubishi Kasei Corporation; US5089494; (1992); (A1) English,

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dicinal Chemistry; vol. 21; nb. 11; (2013); p. 3154 - 3163, View in Reaxys; Tran, Ly Dieu; Roane, James; Daugulis, Olafs; Angewandte Chemie - International Edition; vol. 52; nb. 23; (2013); p. 6043 - 6046; Angew. Chem.; vol. 125; nb. 23; (2013); p. 6159 - 6162,4, View in Reaxys; Degoey, David A.; Betebenner, David A.; Grampovnik, David J.; Liu, Dachun; Pratt, John K.; Tufano, Michael D.; He, Wenping; Krishnan, Preethi; Pilot-Matias, Tami J.; Marsh, Kennan C.; Molla, Akhteruzzaman; Kempf, Dale J.; Maring, Clarence J.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 12; (2013); p. 3627 - 3630, View in Reaxys; Suzuki, Chiharu; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; Organic Letters; vol. 15; nb. 15; (2013); p. 3990 - 3993, View in Reaxys; Patent; Nippon Soda Co., Ltd.; FURUKAWA Hironori; NAKAMURA Takehiko; TAMAI Tetsuo; HANAI Daisuke; EP2628724; (2013); (A1) English, View in Reaxys; Nadres, Enrico T.; Santos, Gerson Ivan Franco; Shabashov, Dmitry; Daugulis, Olafs; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9689 - 9714, View in Reaxys; Shultz, Michael D.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 21; (2013); p. 5980 - 5991, View in Reaxys; Chen, Xiao-Tao; Pitis, Philip; Liu, Guodong; Yuan, Catherine; Gotchev, Dimitar; Cowan, Conrad L.; Rominger, David H.; Koblish, Michael; Dewire, Scott M.; Crombie, Aimee L.; Violin, Jonathan D.; Yamashita, Dennis S.; Journal of Medicinal Chemistry; vol. 56; nb. 20; (2013); p. 8019 - 8031, View in Reaxys; Harrington, Paul E.; Bourbeau, Matthew P.; Fotsch, Christopher; Frohn, Michael; Pickrell, Alexander J.; Reichelt, Andreas; Sham, Kelvin; Siegmund, Aaron C.; Bailis, Julie M.; Bush, Tammy; Escobar, Sonia; Hickman, Dean; Heller, Scott; Hsieh, Faye; Orf, Jessica N.; Rong, Minqing; San Miguel, Tisha; Tan, Helming; Zalameda, Leeanne; Allen, John G.; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 23; (2013); p. 6396 - 6400, View in Reaxys; Debenham, John S.; Graham, Thomas H.; Verras, Andreas; Zhang, Yong; Clements, Matthew J.; Kuethe, Jeffrey T.; Madsen-Duggan, Christina; Liu, Wensheng; Bhatt, Urmi R.; Chen, Dunlu; Chen, Qing; Garcia-Calvo, Margarita; Geissler, Wayne M.; He, Huaibing; Li, Xiaohua; Lisnock, Jeanmarie; Shen, Zhu; Tong, Xinchun; Tung, Elaine C.; Wiltsie, Judyann; Xu, Suoyu; Hale, Jeffrey J.; Pinto, Shirly; Shen, Dong-Ming; Bioorganic and Medicinal Chemistry Letters; vol. 23; nb. 23; (2013); p. 6228 - 6233, View in Reaxys; Basarab, Gregory S.; Manchester, John I.; Bist, Shanta; Boriack-Sjodin, P. Ann; Dangel, Brian; Illingworth, Ruth; Sherer, Brian A.; Sriram, Shubha; Uria-Nickelsen, Maria; Eakin, Ann E.; Journal of Medicinal Chemistry; vol. 56; nb. 21; (2013); p. 8712 - 8735, View in Reaxys; Hamada, Yoshio; Suzuki, Kenji; Nakanishi, Tomoya; Sarma, Diganta; Ohta, Hiroko; Yamaguchi, Ryoji; Yamasaki, Moe; Hidaka, Koushi; Ishiura, Shoichi; Kiso, Yoshiaki; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 2; (2014); p. 618 - 623, View in Reaxys; Gu, Qing; Al Mamari, Hamad H.; Graczyk, Karolina; Diers, Emelyne; Ackermann, Lutz; Angewandte Chemie - International Edition; vol. 53; nb. 15; (2014); p. 3868 - 3871; Angew.Chem.Int.Ed.; vol. 126; nb. 15; (2014); p. 3949 - 3952,4, View in Reaxys; Jaudzems, Kristaps; Tars, Kaspars; Maurops, Gundars; Ivdra, Natalija; Otikovs, Martins; Leitans, Janis; Kanepe-Lapsa, Iveta; Domraceva, Ilona; Mutule, Ilze; Trapencieris, Peteris; Blackman, Michael J.; Jirgensons, Aigars; ACS Medicinal Chemistry Letters; vol. 5; nb. 4; (2014); p. 373 - 377, View in Reaxys; Suzuki, Chiharu; Morimoto, Keisuke; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; Advanced Synthesis and Catalysis; vol. 356; nb. 7; (2014); p. 1521 - 1526, View in Reaxys; Patent; THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING; SCOBIE, Martin; HELLEDAY, Thomas; KOOLMEISTER, Tobias; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; WO2014/84778; (2014); (A1) English, View in Reaxys; Basarab, Gregory S.; Hill, Pamela J.; Garner, C. Edwin; Hull, Ken; Green, Oluyinka; Sherer, Brian A.; Dangel, P. Brian; Manchester, John I.; Bist, Shanta; Hauck, Sheila; Zhou, Fei; Uria-Nickelsen, Maria; Illingworth, Ruth; Alm, Richard; Rooney, Mike; Eakin, Ann E.; Journal of Medicinal Chemistry; vol. 57; nb.

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Effect (Pharmacological Data)

L-alanine transport; effect on

Species or Test-System (Pharmacological Data)

dog intestinal brush-border membrane vesicles

Concentration (Pharmacological Data)

5 - 10 mmol/l

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Kind of Dosing (Pharma- title comp. in incubation buffer (100 mM mannitol, 10 mM Hepes, 100 mM NaCl or KCl, pH cological Data) 7.5 adjusted with KOH) Method (Pharmacological Data)

cis-inhibitory effect of title comp. studied by rapid filtration technique; suspension incub. with title comp. and 3H-labelled and unlabelled L-alanine at 25 deg C for 15 s in NaCl or KClcont. buffer (Na(1+)-dependent or -independent transport, resp.)

Further Details (Pharma- vesicles isolated from small intestine by calcium precipitation method and suspensed in cological Data) buffer containing mannitol and Hepes; suspension of vesicles preincubated at 25 deg C for 2 min; controls incubated in transport buffer without title comp.

Results

title comp. dose-dependently inhibited only Na(1+)-dependent L-alanine uptake

Hatanaka, Takahiro; Nabuchi, Yoshiaki; Ushio, Hidetoshi; Journal of Pharmacy and Pharmacology; vol. 54; nb. 4; (2002); p. 549 - 554, View in Reaxys 3 of 3

Effect (Pharmacological Data)

cardiovascular

Species or Test-System (Pharmacological Data)

white mongrel rats

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

0.1 mg/kg/min

Method (Pharmacological Data)

rats (250-280 g) narcotized; changes in the cardiac cycle duration (R-R interval) and the average arterial pressure evaluated for adenosine (0.1 mg/kg) injected i.v. 10 min after start of title comp. infusion; infusion continued after injection

Results

the adenosine effects did not change significantly

Sapronov, N. S.; Eliseev, V. V.; Torkunov, P. A.; Krylova, I. B.; Evdokimova, N. R.; Pharmaceutical Chemistry Journal; vol. 32; nb. 11; (1998); p. 575 - 577; Khimiko-Farmatsevticheskii Zhurnal; vol. 32; nb. 11; (1998); p. 9 - 11, View in Reaxys Concentration in the Environment (1) 1 of 1

Media (Concentration in the Environment)

coal gasification effluent

Location

Nanjing, China

Contamination Concentration

0.098 mg/l

Method, Remarks (Con- filtered effluent sample 1 was passed through C18 SPE column; elution with 25, 50, 75, 80, centration in the Environ- 85, 90, 95, 100 percent methanol/water solutions; 50 percent fraction of effluent sample 1; ment) GC-MS Jin; Yang; Yu; Yin; Bulletin of Environmental Contamination and Toxicology; vol. 63; nb. 3; (1999); p. 399 - 406, View in Reaxys

Reaxys ID 3687602 View in Reaxys

NH 2 Cl

2/7 Chemical Name: α,α-dimethylbenzylamine hydrochloride; 1methyl-1-phenyl-ethylamine; hydrochloride; 1-Methyl-1-phenylaethylamin; Hydrochlorid; dimethylbenzyl ammonium chloride Linear Structure Formula: C9H13N*ClH Molecular Formula: C9H13N*ClH Molecular Weight: 171.67 Type of Substance: isocyclic InChI Key: GFHYLSUXGARRTC-UHFFFAOYSA-N Note:

H

Substance Label (1) Label References IIIn

Tomashenko; Sokolov; Tomashevskii; Potekhin; De Meijere; Russian Journal of Organic Chemistry; vol.

43; nb. 10; (2007); p. 1421 - 1426, View in Reaxys

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Patent-Specific Data (2) Location in Patent References Patent; G.D. Searle and Co.; US6337398; (2002); (B1) English, View in Reaxys Claim

Patent; Drew Chemical Corporation; US4724142; (1988); (A1) English, View in Reaxys; Patent; Drew Chemical Corporation; US4725613; (1988); (A1) English, View in Reaxys; Patent; Walex Products Company; US4818524; (1989); (A1) English, View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

240 - 241

Cope; Foster; Towle; Journal of the American Chemical Society; vol. 71; (1949); p. 3929,3933, View in Reaxys 2 of 3

Melting Point [°C]

240

Comment (Melting Point) Decomposition.

Baker; Ingold; Journal of the Chemical Society; (1927); p. 262, View in Reaxys 3 of 3

Melting Point [°C]

235.5

Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33, View in Reaxys

Reaxys ID 9478472 View in Reaxys

3/7 Linear Structure Formula: C9H11D2N Molecular Formula: C9H13N Molecular Weight: 137.193 Type of Substance: isocyclic InChI Key: KDFDOINBXBEOLZ-QFIQSOQBSA-N Note:

2H

NH 2 2H

Reaxys ID 17012056 View in Reaxys

4/7 Chemical Name: bis-(2-ammonium-2-phenylpropane) sulfate; 1methyl-2-phenyl-ethylamine sulfate; 1-Methyl-2-phenyl-aethylamin-sulfat Linear Structure Formula: 2{C6H5CH2CH(CH3)NH3}(1+)*SO4 (2-)={C H N}2SO 9 14 4 Molecular Formula: 2C9H14N*O4S Molecular Weight: 368.497 InChI Key: XJUUTOHHKNYREC-UHFFFAOYSA-N Note:

OH 2

NH 2 S O O

HO

Reaxys ID 3720792 View in Reaxys

NH 2

5/7

O

Chemical Name: 1-methyl-1-phenyl-ethylamine; nitrite; 1-Methyl-1-phenyl-aethylamin; Nitrit Linear Structure Formula: C9H13N*HNO2 Molecular Formula: C9H13N*HNO2 Molecular Weight: 182.222 Type of Substance: isocyclic InChI Key: SWWADPQTWRZAAE-UHFFFAOYSA-N Note:

OH N

Melting Point (1) 1 of 1

Melting Point [°C]

98 - 99

Comment (Melting Point) Decomposition.

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Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33, View in Reaxys

Reaxys ID 3834567 View in Reaxys

6/7 Chemical Name: 1-methyl-1-phenyl-ethylamine; picrate; 1Methyl-1-phenyl-aethylamin; Picrat Linear Structure Formula: C9H13N*C6H3N3O7 Molecular Formula: C6H3N3O7*C9H13N Molecular Weight: 364.315 Type of Substance: isocyclic InChI Key: UHMJLNUMSLGTGY-UHFFFAOYSA-N Note:

O O

N O

NH 2 HO

N O

O

N O

Melting Point (1) 1 of 1

Melting Point [°C]

237

Comment (Melting Point) Decomposition.

Girault-Vexlearschi; Bulletin de la Societe Chimique de France; (1956); p. 589,596, View in Reaxys

Reaxys ID 4998970 View in Reaxys

7/7 CAS Registry Number: 72235-69-9 Chemical Name: cumylamine-d6 Linear Structure Formula: C9H7D6N Molecular Formula: C9H13N Molecular Weight: 141.161 Type of Substance: isocyclic InChI Key: KDFDOINBXBEOLZ-WFGJKAKNSA-N Note:

2H 2H

2H

NH 2 2H 2H

Boiling Point (1) Boiling Point [°C] 74 - 75

2H

Pressure (Boiling Point) [Torr]

References

10

Leffler, J. E.; Zupancic, J. J.; Journal of the American Chemical Society; vol. 102; nb. 1; (1980); p. 259 - 267, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Leffler, J. E.; Zupancic, J. J.; Journal of the American Chemical Society; vol. 102; nb. 1; (1980); p. 259 - 267, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3320 - 1285 cm**(-1)

Leffler, J. E.; Zupancic, J. J.; Journal of the American Chemical Society; vol. 102; nb. 1; (1980); p. 259 - 267, View in Reaxys

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