N-ethyl-1-phenylcyclohexan-1-amine (Eticyclidine) [CAS 2201-15-2; InChIKey IFYLVUHLOOCYBG-UHF

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NH

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3 substances in Re2016-03-25 07h:12m:24s (EST) axys

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Reaxys ID 2693343 View in Reaxys

1/3 CAS Registry Number: 2201-15-2 Chemical Name: Cyclohexamine; ethyl-(1-phenyl-cyclohexyl)amine; Aethyl-(1-phenyl-cyclohexyl)-amin; N-ethyl-1-phenylcyclohexylamine; cyclohexamine; N-<1-Phenyl-cyclohexyl>-aethylamin; Aethyl-<1-phenyl-cyclohexyl>-amin Linear Structure Formula: C14H21N Molecular Formula: C14H21N Molecular Weight: 203.327 Type of Substance: isocyclic InChI Key: IFYLVUHLOOCYBG-UHFFFAOYSA-N Note:

NH

Substance Label (10) Label References 3

Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys; Bailey; Legault; Journal - Association of Official Analytical Chemists; vol. 62; nb. 5; (1979); p. 1124 - 1137, View in Reaxys; Kalir; Teomy; Amir; Fuchs; Lee; Holsztynska; Rocki; Domino; Journal of Medicinal Chemistry; vol. 27; nb. 10; (1984); p. 1267 - 1271, View in Reaxys

1h

Brine; Williams; Boldt; Carroll; Journal of Heterocyclic Chemistry; vol. 16; nb. 7; (1979); p. 1425 - 1429, View in Reaxys

IV

Bailey; Journal of Pharmaceutical Sciences; vol. 67; nb. 6; (1978); p. 885 - 886, View in Reaxys

II

Kalir et al.; European Journal of Medicinal Chemistry; vol. 13; (1978); p. 17,18, View in Reaxys

s.S.2

Patent; Sokolovsky; Mordechai; DE2339342; (1974); Chem.Abstr.; vol. 80; nb. 132908, View in Reaxys

1

Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

11

Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

18

Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

9

Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

8

Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

Patent-Specific Data (1) Location in Patent References Claim

Patent; STRATTON, CHARLES W; MITCHELL, WILLIAM M; US2001/2421; (2001); (A1) English, View in Reaxys

Derivative (14) Comment (Deriva- References tive) HCl: F: 233-236grad; IR sp.; UV

Bailey; Legault; Journal - Association of Official Analytical Chemists; vol. 62; nb. 5; (1979); p. 1124 - 1137, View in Reaxys

Hydrochlorid: F: 232-235grad (Tab.3); 13CNMR (Tab.1)

Brine; Williams; Boldt; Carroll; Journal of Heterocyclic Chemistry; vol. 16; nb. 7; (1979); p. 1425 - 1429, View in Reaxys

HCl: F: 234-236grad (unkorr.)

Kalir et al.; European Journal of Medicinal Chemistry; vol. 13; (1978); p. 17,18, View in Reaxys

Hydrochlorid: F: 232-234grad, IR, 1H-NMR, MS

Bailey; Journal of Pharmaceutical Sciences; vol. 67; nb. 6; (1978); p. 885 - 886, View in Reaxys

Hydrochlorid (ver- Patent; Sokolovsky; Mordechai; DE2339342; (1974); Chem.Abstr.; vol. 80; nb. 132908, View in Reaxys mutlich): F: 235grad (S.7) Hydrochlorid C14H21N*HCl. mp: 240-242grad<unkorr.>, 236-237grad<un-

Maddox,V.H. et al.; J. Med. Chem.; vol. 8; (1965); p. 230 - 235, View in Reaxys

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korr.>; pk(a)': 9.7 <50percentig.aq.MeOH> Pikrat: F: 158-159grad

Patent; Tanabe; JP1908767; (1960); Chem.Abstr.; vol. 69; nb. 10195f; (1968), View in Reaxys

Hydrochlorid: F: 230grad

Patent; Tanabe; JP1908767; (1960); Chem.Abstr.; vol. 69; nb. 10195f; (1968), View in Reaxys

Hydrochlorid: F: 236-237grad

Patent; Godefroi, Parcell (Parke, Davis Co.); US3145229; (1960); Chem.Abstr.; vol. 61; nb. 9434a; (1964), View in Reaxys

Hydrochlorid: F: Patent; Parke, Davis u.Co.; US3097136; (1960); Chem.Abstr.; vol. 59; nb. 13881; (1963), View in Reaxys 230-237grad, Ae., Isopropylalk. HCl-Salz, F: 230grad

Patent; Tanabe Seiyaku Co.Ltd.; JP652662; (1959); Chem.Abstr.; vol. 58; nb. 13842; (1963), View in Reaxys

Picrat, F: 158-159grad

Patent; Tanabe Seiyaku Co.Ltd.; JP652662; (1959); Chem.Abstr.; vol. 58; nb. 13842; (1963), View in Reaxys

Hydrochlorid. mp: 236-237grad

Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

Hydrochlorid. mp: Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys 236-237grad<aus Propan-2-ol +Et2O> Melting Point (2) 1 of 2

Melting Point [°C]

221

Patent; Sokolovsky; Mordechai; DE233942; (1974); Chem.Abstr.; vol. 80; nb. 132908, View in Reaxys 2 of 2

Melting Point [°C]

95

Patent; Tanabe Seiyaku Co.Ltd.; JP652662; (1959); Chem.Abstr.; vol. 58; nb. 13842; (1963), View in Reaxys Boiling Point (7) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

103 - 105

0.5

Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys

69 - 71

0.04

Maddox,V.H. et al.; J. Med. Chem.; vol. 8; (1965); p. 230 - 235, View in Reaxys

95

0.3

Patent; Tanabe; JP1908767; (1960); Chem.Abstr.; vol. 69; nb. 10195f; (1968), View in Reaxys

104 - 108

2.5

Patent; Godefroi, Parcell (Parke, Davis Co.); US3145229; (1960); Chem.Abstr.; vol. 61; nb. 9434a; (1964), View in Reaxys; Patent; Parke, Davis u.Co.; US3097136; (1960); Chem.Abstr.; vol. 59; nb. 13881; (1963), View in Reaxys; Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

114 - 116

5

Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

110 - 112

2.5

Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys

85 - 89

0.1

Chiavarelli et al.; Gazzetta Chimica Italiana; vol. 83; (1953); p. 347,354, View in Reaxys

Refractive Index (3) Refractive Index Wavelength (Refractive Index) [nm]

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

1.5324

589

20

Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys

1.5285

589

25.5

Maddox,V.H. et al.; J. Med. Chem.; vol. 8; (1965); p. 230 - 235, View in Reaxys

1.5299

589

19

Chiavarelli et al.; Gazzetta Chimica Italiana; vol. 83; (1953); p. 347,354, View in Reaxys

Further Information (2)

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Description (Further Information)

References

Further information

Bailey; Legault; Journal - Association of Official Analytical Chemists; vol. 62; nb. 5; (1979); p. 1124 - 1137, View in Reaxys

Further information

Patent; Sokolovsky; Mordechai; DE2339342; (1974); Chem.Abstr.; vol. 80; nb. 132908, View in Reaxys

Liquid/Liquid Systems (MCS) (1) 1 of 1

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Kalir et al.; European Journal of Medicinal Chemistry; vol. 13; (1978); p. 17,18, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

1H

Bailey; Journal of Pharmaceutical Sciences; vol. 67; nb. 6; (1978); p. 885 - 886, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

IR

Bailey; Journal of Pharmaceutical Sciences; vol. 67; nb. 6; (1978); p. 885 - 886, View in Reaxys Mass Spectrometry (1) References Bailey; Legault; Journal - Association of Official Analytical Chemists; vol. 62; nb. 5; (1979); p. 1124 - 1137, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Maddox,V.H. et al.; J. Med. Chem.; vol. 8; (1965); p. 230 - 235, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Maddox,V.H. et al.; J. Med. Chem.; vol. 8; (1965); p. 230 - 235, View in Reaxys; Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys; Patent; STRATTON, CHARLES W; MITCHELL, WILLIAM M; US2001/2421; (2001); (A1) English, View in Reaxys; Brine; Williams; Boldt; Carroll; Journal of Heterocyclic Chemistry; vol. 16; nb. 7; (1979); p. 1425 - 1429, View in Reaxys; Chiavarelli et al.; Gazzetta Chimica Italiana; vol. 83; (1953); p. 347,354, View in Reaxys; Kalir et al.; European Journal of Medicinal Chemistry; vol. 13; (1978); p. 17,18, View in Reaxys; Patent; Tanabe; JP1908767; (1960); Chem.Abstr.; vol. 69; nb. 10195f; (1968), View in Reaxys; Patent; Godefroi, Parcell (Parke, Davis Co.); US3145229; (1960); Chem.Abstr.; vol. 61; nb. 9434a; (1964), View in Reaxys; Bailey; Journal of Pharmaceutical Sciences; vol. 67; nb. 6; (1978); p. 885 - 886, View in Reaxys; Patent; Parke, Davis u.Co.; US3097136; (1960); Chem.Abstr.; vol. 59; nb. 13881; (1963), View in Reaxys; Patent; Parke; Davis and Co.; GB861350; (1958); Chem.Abstr.; vol. 55; nb. 17583; (1961), View in Reaxys; Bailey; Legault; Journal - Association of Official Analytical Chemists; vol. 62; nb. 5; (1979); p. 1124 - 1137, View in Reaxys; Patent; Tanabe Seiyaku Co.Ltd.; JP652662; (1959); Chem.Abstr.; vol. 58; nb. 13842; (1963), View in Reaxys; Patent; Sokolovsky; Mordechai; DE233942; (1974); Chem.Abstr.; vol. 80; nb. 132908, View in Reaxys; Patent; Sokolovsky; Mordechai; DE2339342; (1974); Chem.Abstr.; vol. 80; nb. 132908, View in Reaxys; Kalir; Teomy; Amir; Fuchs; Lee; Holsztynska; Rocki; Domino; Journal of Medicinal Chemistry; vol. 27; nb. 10; (1984); p. 1267 - 1271, View in Reaxys; Patent; Bristol, David William; King, Clifford Riley; Mitchener, JR., Joseph Pike; Audia, Vicki Haynes; US2008/293695; (2008); (A1) English, View in Reaxys; Hansen, Kasper B.; Mullasseril, Praseeda; Dawit, Sara; Kurtkaya, Natalie L.; Yuan, Hongjie; Vance, Katie M.; Orr, Anna G.; Kvist, Trine; Ogden, Kevin K.; Le, Phuong; Vellano, Kimberly M.; Lewis, Iestyn; Kurtkaya, Serdar; Du, Yuhong; Qui, Min; Murphy; Snyder, James P.; Braeuner-Osborne, Hans; Traynelis, Stephen F.; Journal of Pharmacology and Experimental Therapeutics; vol. 333; nb. 3; (2010); p. 650 - 662, View in Reaxys; Martin; Katzen; Woods; Tripathi; Harris; May; The Journal of pharmacology and experimental therapeutics; vol. 231; nb. 3; (1984); p. 539 - 544, View in Reaxys; Zukin; Proceedings of the National Academy of Sciences of the United States of America; vol. 76; nb. 10; (1979); p. 5372 - 5376, View in Reaxys 2 of 2

Comment (Pharmacological Data)

reversible inhibitor of butyrylcholinesterase (BChE)

Kalir; Teomy; Amir; Fuchs; Lee; Holsztynska; Rocki; Domino; Journal of Medicinal Chemistry; vol. 27; nb. 10; (1984); p. 1267 - 1271, View in Reaxys

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Use (1) Use Pattern

References

Anti-abuse

Patent; Bristol, David William; King, Clifford Riley; Mitchener, JR., Joseph Pike; Audia, Vicki Haynes; US2008/293695; (2008); (A1) English, View in Reaxys

Reaxys ID 6784662 View in Reaxys

2/3 Chemical Name: Cyclohexamine hydrochloride Linear Structure Formula: C14H21N*ClH Molecular Formula: C14H21N*ClH Molecular Weight: 239.788 Type of Substance: isocyclic InChI Key: BDNANSUXFSDBMA-UHFFFAOYSA-N Note:

NH Cl

H

Substance Label (1) Label References 3a

Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

236 - 238

Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Maddox,V.H. et al.; J. Med. Chem.; vol. 8; (1965); p. 230 - 235, View in Reaxys; Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys; Pinchasi; Maayani; Sokolovsky; Biochemical Pharmacology; vol. 26; nb. 18; (1977); p. 1671 - 1679, View in Reaxys; Kloog; Rehavi; Maayani; Sokolovsky; European Journal of Pharmacology; vol. 45; nb. 3; (1977); p. 221 - 227, View in Reaxys

Reaxys ID 6790243 View in Reaxys

3/3 O

O

Linear Structure Formula: C14H21N*C6H3N3O7 Molecular Formula: C6H3N3O7*C14H21N Molecular Weight: 432.433 Type of Substance: isocyclic InChI Key: WKFDERGBAGKQHH-UHFFFAOYSA-N Note:

N

NH

O HO

N O

O

N O

Substance Label (1) Label References 3b

Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

164 - 166

Kalir; Edery; Pelah; Balderman; Porath; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 473 - 477, 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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