2-Methyl-2-propylpropane-1,3-diyl dicarbamate [Meprobamate] by Asch

Query Query

1. Query

NH 2

Results

Date

1 substances in Reaxys

2016-09-03 02h:48m:01s (EST)

H 2N

Search as: As drawn, No mixtures, No charges, No radicals

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Reaxys ID 1788882 View in Reaxys

O NH 2

1/1

CAS Registry Number: 57-53-4 Chemical Name: meprobamate; 4-methyl-4-propyl-2,6-dioxaheptanedioic acid diamide; 4-Methyl-4-propyl-2,6-dioxa-heptandisaeure-diamid; 1,3-Bis-carbamoyloxy-2-methyl-2-propyl-propan; 2,2-Bis-carbamoyloxymethyl-pentan; 2-methyl-2-propyl-1,3propanediol, dicarbamate; Meprobamate Linear Structure Formula: C9H18N2O4 Molecular Formula: C9H18N2O4 Molecular Weight: 218.253 Type of Substance: acyclic InChI Key: NPPQSCRMBWNHMW-UHFFFAOYSA-N Note:

H 2N

Substance Label (1) Label References MBM

Rho, Jong M.; Donevan, Sean D.; Rogawski, Michael A.; Journal of Pharmacology and Experimental Therapeutics; vol. 280; nb. 3; (1997); p. 1383 - 1391, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; EGYT Gyogyszervegyeszeti Gyar; US4316022; (1982); (A1) English, View in Reaxys; Patent; The Regents of the University of Michigan; US4034087; (1977); (A1) English, View in Reaxys

Melting Point (20) 1 of 20

Melting Point [°C]

94 - 96

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys 2 of 20

Melting Point [°C]

97 - 99

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys 3 of 20

Melting Point [°C]

102 - 105

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys 4 of 20

Melting Point [°C]

105 - 106

Ludwig,B.J. et al.; Journal of Medicinal Chemistry; vol. 7; (1964); p. 174 - 177, View in Reaxys; Ludwig,B.J. et al.; Journal of Medicinal Chemistry; vol. 12; nb. 3; (1969); p. 462 - 472, View in Reaxys; Patent; D'Amato; Teotino; FI31146; (1961); Chem.Abstr.; vol. 58; nb. 6702e; (1963), View in Reaxys; Patent; Univ.Oil Prod.; US3173941; (1965); Chem.Abstr.; vol. 62; nb. 16070b; (1965), View in Reaxys 5 of 20

Melting Point [°C]

103 - 104

Patent; Romania, Ministr. Petr. Chem. Ind.; FR1443093; (1966); Chem.Abstr.; vol. 66; nb. 28410v, View in Reaxys 6 of 20

Melting Point [°C]

104 - 106

Patent; Egyesult Gyogyszer es Tapszergyar; HU150469; (1962); Chem.Abstr.; vol. 60; nb. 2790e; (1964), View in Reaxys; Patent; Egyesult Gyogyszer es Tapszergyar; AT239252; (1965); Chem.Abstr.; vol. 62; nb. 16070d; (1965), View in Reaxys 7 of 20

Melting Point [°C]

102 - 102.5

Solvent (Melting Point)

H2O

Fessenden; Coon; Journal of medicinal chemistry; vol. 8; nb. 5; (1965); p. 604 - 608, View in Reaxys 8 of 20

Melting Point [°C]

103 - 105.5

Brandstaetter-Kuhnert et al.; Scientia Pharmaceutica; vol. 31; (1963); p. 140,146, View in Reaxys 9 of 20

Melting Point [°C]

99 - 100

Solvent (Melting Point)

benzene

Schneider,G. et al.; Monatshefte fuer Chemie; vol. 94; (1963); p. 426 - 433, View in Reaxys 10 of 20

Melting Point [°C]

102 - 103

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Solvent (Melting Point)

H2O

Loev,B.; Kormendy,M.F.; Journal of Organic Chemistry; vol. 28; (1963); p. 3421 - 3426, View in Reaxys 11 of 20

Melting Point [°C]

104 - 105

Solvent (Melting Point)

H2O

Ghielmetti; Farmaco, Edizione Scientifica; vol. 11; (1956); p. 1014,1016, View in Reaxys; Ferrari; Chimica e l'Industria (Milan, Italy); vol. 40; (1958); p. 13, View in Reaxys; Patent; Carter Prod.Inc.; US2724720; (1953), View in Reaxys; Patent; Kejha; Hebky; CS97217; Chem.Abstr.; vol. 56; nb. 3355; (1962), View in Reaxys 12 of 20

Melting Point [°C]

104 - 105

Yamamoto,A. et al.; Chemical and Pharmaceutical Bulletin; vol. 10; (1962); p. 522 - 528, View in Reaxys 13 of 20

Melting Point [°C]

105.5 - 106.5

Patent; Millmaster Onyx Corp.; US3219686; (1961); Chem.Abstr.; vol. 64; nb. 6507; (1966), View in Reaxys 14 of 20

Melting Point [°C]

105 - 106

Solvent (Melting Point)

trichloroethene

Ludwig,B.J. et al.; Journal of Medicinal and Pharmaceutical Chemistry; vol. 3; (1961); p. 53 - 64, View in Reaxys 15 of 20

Melting Point [°C]

106

Brandstaetter-Kuhnert; Kuhnert; Scientia Pharmaceutica; vol. 28; (1960); p. 287,302; Chem.Abstr.; nb. 9210; (1960), View in Reaxys 16 of 20

Melting Point [°C]

105

Mastagli,P.; Francois,G.; Bulletin de la Societe Chimique de France; (1960); p. 808 - 810, View in Reaxys 17 of 20

Melting Point [°C]

104.1 - 105.3

Solvent (Melting Point)

xylene

Patent; Berkeley Chem.Corp.; US2837560; (1956), View in Reaxys 18 of 20

Melting Point [°C]

104 - 105.5

Solvent (Melting Point)

aq. ethanol

Patent; Abbott Labor; US2806053; (1956), View in Reaxys 19 of 20

Melting Point [°C]

103 - 105

Patent; Berkeley Chem. Corp.; US2934559; (1956); Chem.Abstr.; nb. 19497; (1960), View in Reaxys 20 of 20

Melting Point [°C]

105 - 106

Solvent (Melting Point)

H2O

Ludwig; Piech; Journal of the American Chemical Society; vol. 73; (1951); p. 5779, View in Reaxys Density (3) 1 of 3

Density [g·cm-3]

1.182

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys 2 of 3

Density [g·cm-3]

1.229

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys 3 of 3

Density [g·cm-3]

1.247

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys Crystal Phase (2) Description (Crys- References tal Phase) Polymorphism

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 1264, View in Reaxys

Rate of transition

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 1264, View in Reaxys

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Further Information (8) Description (Fur- References ther Information) Further information

Brent; Journal - Association of Official Analytical Chemists; vol. 59; (1976); p. 1006,1013, View in Reaxys

Further information

Rouse; Brent; Biomedical Mass Spectrometry; vol. 1; (1974); p. 256,258, View in Reaxys

Further information

Coutts; Journal of pharmaceutical sciences; vol. 62; nb. 5; (1973); p. 769 - 773, View in Reaxys

Further information

Shearer; Rulon; Analytical Profiles of Drug Substances and Excipients; vol. 1; nb. C; (1972); p. 207 - 232, View in Reaxys

Further information

Fales et al.; Archives of Mass Spectral Data; vol. 2; (1971); p. 596, View in Reaxys

Further information

Hamilton; Journal - Association of Official Analytical Chemists; vol. 53; (1970); p. 594,597, View in Reaxys

Further information

Brannon; Hayden; Journal of the Association of Official Agricultural Chemists; vol. 47; (1964); p. 918,927, View in Reaxys

Further information

Hynie; Prokes; Chemicke Zvesti; vol. 18; (1964); p. 425,426, View in Reaxys

Liquid/Liquid Systems (MCS) (2) 1 of 2

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

octanol; H2O

Hansch; Bjorkroth; Leo; Journal of Pharmaceutical Sciences; vol. 76; nb. 9; (1987); p. 663 - 687, View in Reaxys 2 of 2

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

aqueous buffer sol./Et2O (pH=1...13) or CHCl3 (pH=3,7)

Muller; Pharmazie; vol. 38; nb. 7; (1983); p. 462 - 466, View in Reaxys Liquid/Solid Systems (MCS) (1) 1 of 1

Description (Liquid/Solid Eutectic Systems (MCS)) Brandstaetter-Kuhnert; Kuhnert; Scientia Pharmaceutica; vol. 28; (1960); p. 287,302; Chem.Abstr.; nb. 9210; (1960), View in Reaxys; Brandstaetter-Kuhnert et al.; Scientia Pharmaceutica; vol. 31; (1963); p. 140,146, View in Reaxys

Solubility (MCS) (4) 1 of 4

Saturation

in pure solvent

Comment (Solubility (MCS))

equation

Jain, Neera; Yalkowsky, Samuel H.; Journal of Pharmaceutical Sciences; vol. 90; nb. 2; (2001); p. 234 - 252, View in Reaxys 2 of 4

Solubility [g·l-1]

4.02

Saturation

in pure solvent

Temperature (Solubility (MCS)) [°C]

Solvent (Solubility (MCS))

H2O

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys 3 of 4

Solubility [g·l-1]

4.86

Saturation

in pure solvent

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Temperature (Solubility (MCS)) [°C]

Solvent (Solubility (MCS))

H2O

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys 4 of 4

Solubility [g·l-1]

Saturation

in pure solvent

Temperature (Solubility (MCS)) [°C]

Solvent (Solubility (MCS))

H2O

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys Surface Tension (1) References Lerk; Lagas; Boelstra; Broersma; Journal of pharmaceutical sciences; vol. 66; nb. 10; (1977); p. 1480 - 1481, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

15N

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Lycka; Cizmarik; Pharmazie; vol. 42; nb. 4; (1987); p. 271 - 272, View in Reaxys 2 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-15N.

Lycka; Cizmarik; Pharmazie; vol. 42; nb. 4; (1987); p. 271 - 272, View in Reaxys 3 of 3

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Turczan; Kram; Journal of pharmaceutical sciences; vol. 56; nb. 12; (1967); p. 1643 - 1645, View in Reaxys IR Spectroscopy (8) 1 of 8

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1600 - 1100 cm**(-1)

Burger, Artur; Schulte, Karl; Archiv der Pharmazie (Weinheim, Germany); vol. 314; nb. 5; (1981); p. 398 - 408, View in Reaxys 2 of 8

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3600 - 3200 cm**(-1)

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Burger, Artur; Schulte, Karl; Archiv der Pharmazie (Weinheim, Germany); vol. 314; nb. 5; (1981); p. 398 - 408, View in Reaxys 3 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Comment (IR Spectroscopy)

1747 cm**(-1)

Burger, Artur; Schulte, Karl; Archiv der Pharmazie (Weinheim, Germany); vol. 314; nb. 5; (1981); p. 398 - 408, View in Reaxys 4 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1728 - 1585 cm**(-1)

Burger, Artur; Schulte, Karl; Archiv der Pharmazie (Weinheim, Germany); vol. 314; nb. 5; (1981); p. 398 - 408, View in Reaxys 5 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1720 - 1597 cm**(-1)

Burger, Artur; Schulte, Karl; Archiv der Pharmazie (Weinheim, Germany); vol. 314; nb. 5; (1981); p. 398 - 408, View in Reaxys 6 of 8

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3460 - 1070 cm**(-1)

Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys 7 of 8

Description (IR Spectroscopy)

Spectrum

Brannon; Hayden; Journal of the Association of Official Agricultural Chemists; vol. 47; (1964); p. 918,927, View in Reaxys; Hamilton; Journal - Association of Official Analytical Chemists; vol. 53; (1970); p. 594,597, View in Reaxys 8 of 8

Description (IR Spectroscopy)

Bands

Yamamoto,A. et al.; Chemical and Pharmaceutical Bulletin; vol. 10; (1962); p. 522 - 528, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) fragmentation pattern

Vanderford, Brett J.; Pearson, Rebecca A.; Rexing, David J.; Snyder, Shane A.; Analytical Chemistry; vol. 75; nb. 22; (2003); p. 6265 - 6274, View in Reaxys Fales et al.; Archives of Mass Spectral Data; vol. 2; (1971); p. 596, View in Reaxys; Brent; Journal - Association of Official Analytical Chemists; vol. 59; (1976); p. 1006,1013, View in Reaxys; Nelson; Kuhlman; Chang; Journal of pharmaceutical sciences; vol. 63; nb. 12; (1974); p. 1959 - 1960, View in Reaxys; Rouse; Brent; Biomedical Mass Spectrometry; vol. 1; (1974); p. 256,258, View in Reaxys; Coutts; Journal of pharmaceutical sciences; vol. 62; nb. 5; (1973); p. 769 - 773, View in Reaxys

Pharmacological Data (49) 1 of 49

Comment (Pharmacological Data)

Bioactivities present

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Schneider,G. et al.; Monatshefte fuer Chemie; vol. 94; (1963); p. 426 - 433, View in Reaxys; Yamamoto,A. et al.; Chemical and Pharmaceutical Bulletin; vol. 10; (1962); p. 522 - 528, View in Reaxys; Patent; EGYT Gyogyszervegyeszeti Gyar; US4316022; (1982); (A1) English, View in Reaxys; Ludwig,B.J. et al.; Journal of Medicinal Chemistry; vol. 7; (1964); p. 174 - 177, View in Reaxys; Fessenden; Coon; Journal of medicinal chemistry; vol. 8; nb. 5; (1965); p. 604 - 608, View in Reaxys; Ludwig,B.J. et al.; Journal of Medicinal Chemistry; vol. 12; nb. 3; (1969); p. 462 - 472, View in Reaxys; Moffett,R.B. et al.; Journal of Medicinal Chemistry; vol. 14; (1971); p. 963 - 968, View in Reaxys; Turk; Krapcho; Michel; Weinryb; Journal of Medicinal Chemistry; vol. 20; nb. 5; (1977); p. 729 732, View in Reaxys; Clarke; Hill; Koo; Lopano; Maseda; Smith; Soled; VonVeh; Vlattas; Journal of Medicinal Chemistry; vol. 21; nb. 8; (1978); p. 785 - 791, View in Reaxys; Ludwig,B.J. et al.; Journal of Medicinal and Pharmaceutical Chemistry; vol. 3; (1961); p. 53 - 64, View in Reaxys; Mastagli,P.; Francois,G.; Bulletin de la Societe Chimique de France; (1960); p. 808 - 810, View in Reaxys; Loev,B.; Kormendy,M.F.; Journal of Organic Chemistry; vol. 28; (1963); p. 3421 - 3426, View in Reaxys; Canonico,A. et al.; Farmaco, Edizione Scientifica; vol. 23; (1968); p. 383 - 398, View in Reaxys; Doan,L.A.; Chatten,L.G.; Journal of Pharmaceutical Sciences; vol. 54; (1965); p. 1605 - 1609, View in Reaxys; Turczan; Kram; Journal of pharmaceutical sciences; vol. 56; nb. 12; (1967); p. 1643 1645, View in Reaxys; Lerk; Lagas; Boelstra; Broersma; Journal of pharmaceutical sciences; vol. 66; nb. 10; (1977); p. 1480 - 1481, View in Reaxys; Patent; Summers, Neena L.; McWherter, Charles A.; Feng, Yiqing; US2006/172932; (2006); (A1) English, View in Reaxys; Patent; UNIVERSITY OF MANITOBA; WO2006/130982; (2006); (A1) English, View in Reaxys; Ludwig; Piech; Journal of the American Chemical Society; vol. 73; (1951); p. 5779, View in Reaxys; Roth et al.; Journal of the American Pharmaceutical Association (1912-1977); vol. 48; (1959); p. 415, View in Reaxys 2 of 49

Comment (Pharmacological Data)

Bioactivities present

Ghielmetti; Farmaco, Edizione Scientifica; vol. 11; (1956); p. 1014,1016, View in Reaxys; Patent; Berkeley Chem.Corp.; US2837560; (1956), View in Reaxys; Ferrari; Chimica e l'Industria (Milan, Italy); vol. 40; (1958); p. 13, View in Reaxys; Patent; Carter Prod.Inc.; US2724720; (1953), View in Reaxys; Patent; Abbott Labor; US2806053; (1956), View in Reaxys; Wright Jr.; Brabander; Greenblatt; Day; Hardy Jr.; Journal of Medicinal Chemistry; vol. 21; nb. 10; (1978); p. 1087 - 1089, View in Reaxys; Brannon; Hayden; Journal of the Association of Official Agricultural Chemists; vol. 47; (1964); p. 918,927, View in Reaxys; Brandstaetter-Kuhnert; Kuhnert; Scientia Pharmaceutica; vol. 28; (1960); p. 287,302; Chem.Abstr.; nb. 9210; (1960), View in Reaxys; Ott; Hardtmann; Denzer; Frey; Gogerty; Leslie; Trapold; Journal of medicinal chemistry; vol. 11; nb. 4; (1968); p. 777 - 787, View in Reaxys; Brandstaetter-Kuhnert et al.; Scientia Pharmaceutica; vol. 31; (1963); p. 140,146, View in Reaxys; Fales et al.; Archives of Mass Spectral Data; vol. 2; (1971); p. 596, View in Reaxys; Brent; Journal - Association of Official Analytical Chemists; vol. 59; (1976); p. 1006,1013, View in Reaxys; Pifferi; Consonni; Banfi; Diena; Journal of medicinal chemistry; vol. 12; nb. 2; (1969); p. 261 - 266, View in Reaxys; Moffett; Journal of medicinal chemistry; vol. 12; nb. 4; (1969); p. 715 - 715, View in Reaxys; Tsukamoto et al.; Chemical and Pharmaceutical Bulletin; vol. 11; (1963); p. 421,424, View in Reaxys; Patent; Kejha; Hebky; CS97217; Chem.Abstr.; vol. 56; nb. 3355; (1962), View in Reaxys; Patent; Berkeley Chem. Corp.; US2934559; (1956); Chem.Abstr.; nb. 19497; (1960), View in Reaxys; Shearer; Rulon; Analytical Profiles of Drug Substances and Excipients; vol. 1; nb. C; (1972); p. 207 - 232, View in Reaxys; Nelson; Kuhlman; Chang; Journal of pharmaceutical sciences; vol. 63; nb. 12; (1974); p. 1959 - 1960, View in Reaxys; Patent; Millmaster Onyx Corp.; US3219686; (1961); Chem.Abstr.; vol. 64; nb. 6507; (1966), View in Reaxys 3 of 49

Comment (Pharmacological Data)

Bioactivities present

Michotte; Massart; Dryon; Pharmaceutica acta Helvetiae; vol. 52; nb. 6-7; (1977); p. 152 - 153, View in Reaxys; Patent; D'Amato; Teotino; FI31146; (1961); Chem.Abstr.; vol. 58; nb. 6702e; (1963), View in Reaxys; Patent; Romania, Ministr. Petr. Chem. Ind.; FR1443093; (1966); Chem.Abstr.; vol. 66; nb. 28410v, View in Reaxys; Rouse; Brent; Biomedical Mass Spectrometry; vol. 1; (1974); p. 256,258, View in Reaxys; Patent; Egyesult Gyogyszer es Tapszergyar; HU150469; (1962); Chem.Abstr.; vol. 60; nb. 2790e; (1964), View in Reaxys; Hynie; Prokes; Chemicke Zvesti; vol. 18; (1964); p. 425,426, View in Reaxys; Hamilton; Journal - Association of Official Analytical Chemists; vol. 53; (1970); p. 594,597, View in Reaxys; Tsukamoto et al.; Chemical and Pharmaceutical Bulletin; vol. 11; (1963); p. 1134,1138, View in Reaxys; Coutts; Journal of pharmaceutical sciences; vol. 62; nb. 5; (1973); p. 769 773, View in Reaxys; Patent; Univ.Oil Prod.; US3173941; (1965); Chem.Abstr.; vol. 62; nb. 16070b; (1965), View in Reaxys; Patent; Egyesult Gyogyszer es Tapszergyar; AT239252; (1965); Chem.Abstr.; vol. 62; nb. 16070d; (1965), View in Reaxys; Valenta; Bartosova; Protiva; Collection of Czechoslovak Chemical Communications; vol. 45; nb. 2; (1980); p. 517 - 528, View in Reaxys; Albright, J. D.; Moran, D. B.; Wright, W. B.; Collins, J. B.; Beer, B.; et al.; Journal of Medicinal Chemistry; vol. 24; nb. 5; (1981); p. 592 - 600, View in Reaxys; Tagami; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 9; (1980); p. 2642 - 2646, View in Reaxys; Muller; Pharmazie; vol. 38; nb. 7; (1983); p. 462 - 466, View in Reaxys; Melzig; Teuscher; Pharmazie; vol. 41; nb. 8; (1986); p. 604 604, View in Reaxys; Brouillette; Grunewald; Journal of Medicinal Chemistry; vol. 27; nb. 2; (1984); p. 202 - 206, View in Reaxys; Vinogradova, V. I.; Yunusov, M. S.; Rezhepov, Zh.; Sadritdinov, F. F.; Pharmaceutical Chemistry Journal; vol. 17; nb. 1; (1983); p. 30 - 31; Khimiko-Farmatsevticheskii Zhurnal; vol. 17; nb. 1; (1983); p. 44 - 45, View in Reaxys; Lycka; Cizmarik; Pharmazie; vol. 42; nb. 4; (1987); p. 271 - 272, View in Reaxys; Hoffmeister; Benz; Heise; et al.; Arzneimittel-Forschung/Drug Research; vol. 32; nb. 4; (1982); p. 347 - 360, View in Reaxys 4 of 49

Comment (Pharmacological Data)

Bioactivities present

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Burger, Artur; Schulte, Karl; Archiv der Pharmazie (Weinheim, Germany); vol. 314; nb. 5; (1981); p. 398 - 408, View in Reaxys; Muehlenbruch; Winkler; Archiv der Pharmazie; vol. 314; nb. 7; (1981); p. 646 - 648, View in Reaxys; Gilbert; Aylott; Draffan; Sogtrop; Arzneimittel-Forschung/Drug Research; vol. 32; nb. 5; (1982); p. 571 - 574, View in Reaxys; Gilbert; Aylott; Sogtrop; Draffian; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 10; (1984); p. 1323 - 1327, View in Reaxys; Pieri; Schaffner; Scherschlicht; Polc; Sepinwall; Davidson; Moehler; Cumin; Da Prada; Burkard; Keller; Mueller; Gerold; Cook; Haefely; Arzneimittel-Forschung/Drug Research; vol. 31; nb. 12 a; (1981); p. 2180 - 2201, View in Reaxys; du Cailar; Cadi; Jullien; Griffe; ArzneimittelForschung; vol. 31; nb. 12 a; (1981); p. 2239 - 2243, View in Reaxys; Debruyne; Moulin; Camsonne; Bigot; Journal of Pharmaceutical Sciences; vol. 69; nb. 7; (1980); p. 835 - 838, View in Reaxys; Pham Huu Chanh; Navarro Delmasure Ch.; et al.; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 2; (1984); p. 175 - 181, View in Reaxys; Hansch; Bjorkroth; Leo; Journal of Pharmaceutical Sciences; vol. 76; nb. 9; (1987); p. 663 - 687, View in Reaxys; Lenegre; Avril; Fromage; Milinkevitch; Porsolt; Arzneimittel-Forschung/Drug Research; vol. 38; nb. 4; (1988); p. 558 - 560, View in Reaxys; Ramberger, R.; Burger, A.; Schulte, K.; Berichte der Bunsen-Gesellschaft; vol. 84; nb. 12; (1980); p. 1261 - 1264, View in Reaxys; Sparatore; Novelli; Farmaco; vol. 52; nb. 8-9; (1997); p. 509 - 521, View in Reaxys; Jain, Neera; Yalkowsky, Samuel H.; Journal of Pharmaceutical Sciences; vol. 90; nb. 2; (2001); p. 234 - 252, View in Reaxys; Rho, Jong M.; Donevan, Sean D.; Rogawski, Michael A.; Journal of Pharmacology and Experimental Therapeutics; vol. 280; nb. 3; (1997); p. 1383 - 1391, View in Reaxys; Vanderford, Brett J.; Pearson, Rebecca A.; Rexing, David J.; Snyder, Shane A.; Analytical Chemistry; vol. 75; nb. 22; (2003); p. 6265 6274, View in Reaxys; Obach, R. Scott; Huynh, Phuong; Allen, Mary C.; Beedham, Christine; Journal of Clinical Pharmacology; vol. 44; nb. 1; (2004); p. 7 - 19, View in Reaxys; Mahar Doan, Kelly M.; Humphreys, Joan E.; Webster, Lindsey O.; Wring, Stephen A.; Shampine, Larry J.; Serabjit-Singh, Cosette J.; Adkison, Kimberly K.; Polli, Joseph W.; Journal of Pharmacology and Experimental Therapeutics; vol. 303; nb. 3; (2002); p. 1029 1037, View in Reaxys; Ator, Nancy A.; Griffiths, Roland R.; Journal of Pharmacology and Experimental Therapeutics; vol. 282; nb. 3; (1997); p. 1442 - 1457, View in Reaxys; Votano, Joseph R.; Parham, Marc; Hall, L. Mark; Hall, Lowell H.; Kier, Lemont B.; Oloff, Scott; Tropsha, Alexander; Journal of Medicinal Chemistry; vol. 49; nb. 24; (2006); p. 7169 - 7181, View in Reaxys; Summerfield, Scott G.; Read, Kevin; Begley, David J.; Obradovic, Tanja; Hidalgo, Ismael J.; Coggon, Sara; Lewis, Ann V.; Porter, Rod A.; Jeffrey, Phil; Journal of Pharmacology and Experimental Therapeutics; vol. 322; nb. 1; (2007); p. 205 - 213, View in Reaxys 5 of 49

Comment (Pharmacological Data)

Bioactivities present

Patent; The Regents of the University of Michigan; US4034087; (1977); (A1) English, View in Reaxys; Lee, Ivan T.; Chen, Shiuhwei; Schetz, John A.; European Journal of Pharmacology; vol. 578; nb. 2-3; (2008); p. 123 - 136, View in Reaxys; Friden, Markus; Winiwarter, Susanne; Jerndal, Gunilla; Bengtsson, Ola; Hong, Wan; Bredberg, Ulf; Hammarlund-Udenaes, Margareta; Antonsson, Madeleine; Journal of Medicinal Chemistry; vol. 52; nb. 20; (2009); p. 6233 - 6243, View in Reaxys; Vincent, Fabien; Nguyen, Margaret T.; Emerling, Daniel E.; Kelly, Michael G.; Duncton, Matthew A.J.; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 23; (2009); p. 6793 6796, View in Reaxys; Kung, Ching-Hsin; Kwon, Chul-Hoon; Medicinal Chemistry Research; vol. 19; nb. 5; (2010); p. 498 - 513, View in Reaxys; Hen, Naama; Bialer, Meir; Yagen, Boris; Journal of Medicinal Chemistry; vol. 55; nb. 6; (2012); p. 2835 - 2845, View in Reaxys; Dagenais, Claude; Avdeef, Alex; Tsinman, Oksana; Dudley, Adam; Beliveau, Richard; European Journal of Pharmaceutical Sciences; vol. 38; nb. 2; (2009); p. 121 - 137, View in Reaxys; Gonzalez, Lorie A.; Gatch, Michael B.; Taylor, Cynthia M.; Bell-Horner, Cathy L.; Forster, Michael J.; Dillon, Glenn H.; Journal of Pharmacology and Experimental Therapeutics; vol. 329; nb. 2; (2009); p. 827 - 837, View in Reaxys; Benet, Leslie Z.; Broccatelli, Fabio; Oprea, Tudor I.; AAPS Journal; vol. 13; nb. 4; (2011); p. 519 - 547, View in Reaxys; Zimmerlin, Alfred; Trunzer, Markus; Faller, Bernard; Drug Metabolism and Disposition; vol. 39; nb. 6; (2011); p. 1039 - 1046, View in Reaxys; Aboul-Enein; El-Azzouny; Saleh; Maklad; Mini-Reviews in Medicinal Chemistry; vol. 12; nb. 7; (2012); p. 671 - 700, View in Reaxys; Aeberli; Gogerty; Houlihan; Journal of medicinal chemistry; vol. 10; nb. 4; (1967); p. 636 - 642, View in Reaxys; Valzelli; Giacalone; Garattini; European journal of pharmacology; vol. 2; nb. 2; (1967); p. 144 - 146, View in Reaxys; Casadio; Pala; Crescenzi; Marazzi-Uberti; Coppi; Turba; Journal of medicinal chemistry; vol. 11; nb. 1; (1968); p. 97 - 100, View in Reaxys; Loev; Macko; Fried; Journal of medicinal chemistry; vol. 12; nb. 5; (1969); p. 854 - 859, View in Reaxys; Harada; Yamashita; Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan; vol. 89; nb. 9; (1969); p. 1205 1211, View in Reaxys; Ludwig; Powell; Berger; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 462 - 472, View in Reaxys; Jenis; Payne; Goldbaum; JAMA : the journal of the American Medical Association; vol. 207; nb. 2; (1969); p. 361 - 362, View in Reaxys; Nelson; Sherwood; Journal of Medicinal Chemistry; vol. 17; nb. 8; (1974); p. 904 - 907, View in Reaxys; Aoyagi; Kimura; Murata; Chemical and Pharmaceutical Bulletin; vol. 22; nb. 5; (1974); p. 1008 - 1013, View in Reaxys 6 of 49

Comment (Pharmacological Data)

Bioactivities present

Speth; Wastek; Johnson; Yamamura; Life Sciences; vol. 22; nb. 10; (1978); p. 859 - 866, View in Reaxys; Allen; Greenblatt; Noel; Clinical Toxicology; vol. 11; nb. 5; (1977); p. 501 - 515, View in Reaxys; Mohler; Okada; Heitz Ph.; Ulrich; Life Sciences; vol. 22; nb. 11; (1978); p. 985 - 996, View in Reaxys; Frey, Hans-Hasso; Bartels, Imke; Epilepsy Research; vol. 27; nb. 3; (1997); p. 151 - 164, View in Reaxys; Rex; Voigt; Voits; Fink; Pharmacology Biochemistry and Behavior; vol. 59; nb. 3; (1998); p. 677 - 683, View in Reaxys; De Vry; Benz; Schreiber; Traber; European Journal of Pharmacology; vol. 249; nb. 3; (1993); p. 331 - 339, View in Reaxys; Heffner; Downs; Meltzer; Wiley; Williams; Journal of Pharmacology and Experimental Therapeutics; vol. 251; nb. 1; (1989); p. 105 - 112, View in Reaxys; Dennison; Edwards; Volans; Human Toxicology; vol. 4; nb. 2; (1985); p. 215 - 217, View in Reaxys; Albright; Moran; Wright Jr.; et al.; Journal of Medicinal Chemistry; vol. 24; nb. 5; (1981); p. 592 -

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600, View in Reaxys; Albright; Moran; Wright Jr.; Collins; Beer; Lippa; Greenblatt; Journal of medicinal chemistry; vol. 24; nb. 5; (1981); p. 592 - 600, View in Reaxys; Sternbach; Journal of Medicinal Chemistry; vol. 22; nb. 1; (1979); p. 1 - 7, View in Reaxys; Krapcho; Turk; Journal of Medicinal Chemistry; vol. 22; nb. 2; (1979); p. 207 - 210, View in Reaxys; Cymbalist; Shapero; Journal of Pharmacy and Pharmacology; vol. 26; nb. 2; (1974); p. 109 - 112, View in Reaxys; Moffett; Robert; Skaletzky; Journal of medicinal chemistry; vol. 14; nb. 10; (1971); p. 963 - 968, View in Reaxys; Minoli; Marazzi-Uberti; Casadio; Journal of medicinal chemistry; vol. 15; nb. 9; (1972); p. 998 998, View in Reaxys; Casadio; Pala; Mantegani; Marazzi-Uberti; Coppi; Turba; Journal of medicinal chemistry; vol. 13; nb. 6; (1970); p. 1092 - 1095, View in Reaxys; Franko; Ward; Gilbert; Woodard; Toxicology and applied pharmacology; vol. 19; nb. 1; (1971); p. 93 - 102, View in Reaxys; Casadio; Pala; Bruzzese; Turba; Marazzi-Uberti; Journal of medicinal chemistry; vol. 13; nb. 3; (1970); p. 418 - 421, View in Reaxys; BERGER, F M; The Journal of pharmacology and experimental therapeutics; vol. 112; nb. 4; (1954); p. 413 - 23, View in Reaxys; Patent; Mendes; Etienne; Vernieres; Jean-Claude; Simiaud; Jacques; Keane; Peter E.; (6 pag.); US4996213; (1991), View in Reaxys 7 of 49

Comment (Pharmacological Data)

Bioactivities present

FUJIMORI, H; COBB, D P; The Journal of pharmacology and experimental therapeutics; vol. 148; (1965); p. 151 7, View in Reaxys; HEISE, G A; BOFF, E; Psychopharmacology; vol. 3; (1962); p. 264 - 82, View in Reaxys; Spencer, P S; British journal of pharmacology and chemotherapy; vol. 25; nb. 2; (1965); p. 442 - 55, View in Reaxys; Patent; YOUNG, James, W.; BRANDT, Steven; (42 pag.); WO2009/310788; (1993); (A1), View in Reaxys; Patent; Vernieres; Jean-Claude; Mendes; Etienne; Morre; Michel; Keane; Peter; Simiand; Jacques; (14 pag.); US4788188; (1988), View in Reaxys; BERGER, F M; The Journal of pharmacology and experimental therapeutics; vol. 104; nb. 2; (1952); p. 229 - 33, View in Reaxys; RANDALL, L O; SCHALLEK, W; HEISE, G A; KEITH, E F; BAGDON, R E; The Journal of pharmacology and experimental therapeutics; vol. 129; (1960); p. 163 - 71, View in Reaxys; WITKIN, L B; SPITALETTA, P; PLUMMER, A J; Arch Int Pharmacodyn Ther (1899-1996); vol. 124; (1960); p. 105 - 15, View in Reaxys; Horovitz, Z P; Piala, J J; High, J P; Burke, J C; Leaf, R C; International journal of neuropharmacology; vol. 5; nb. 6; (1966); p. 405 - 11, View in Reaxys; BRUCE W. HORROM; T. E. LYNES; Journal of medicinal chemistry; vol. 6; nb. 5; (1963); p. 528 - 532, View in Reaxys; B. J. Ludwig; Frank J. Stiefel; L. S. Powell; Julius Diamond; Journal of medicinal chemistry; vol. 7; nb. 2; (1964); p. 174 - 177, View in Reaxys; J.D.McColl; F.L.Chubb; C.F.Lee; A.Hajdd; J.Komlossy; Journal of medicinal chemistry; vol. 6; nb. 5; (1963); p. 584 - 587, View in Reaxys; W.H . HUNTER; R,. M. QUINTON; P. H. SHERMAN; C. R. WORTHING; R. J. BOSCOTT; Journal of medicinal chemistry; vol. 7; nb. 2; (1964); p. 167 - 174, View in Reaxys; P. Skolnick; S.M. Paul; Annual reports in medicinal chemistry; vol. 16; (1981); p. 21 - 29, View in Reaxys; R. Ian Fryer; Annual reports in medicinal chemistry; vol. 5; (1969); p. 1 - 30, View in Reaxys; Cornelius K. Cain; Annual reports in medicinal chemistry; vol. 1; (1965); p. 30 - 39, View in Reaxys; Roszkowski AP; The Journal of pharmacology and experimental therapeutics; vol. 129; (1960); p. 75 - 81, View in Reaxys; European journal of medicinal chemistry; vol. 12; (1977); p. 447, View in Reaxys; Dissertationes Pharmaceuticae, 1971, 23, 281.; vol. 23; (1971); p. 281, View in Reaxys; The Merck Index, 12th edition, View in Reaxys 8 of 49

Comment (Pharmacological Data)

Bioactivities present

The Merck Index, 5908, 12 th edition, 1996; (1996), View in Reaxys; American Hospital Formulary Service Drug Information, View in Reaxys; BARNES J.; J. Ir. Med. Assoc.; vol. 41; nb. 244; (1957); p. 119 - 120, View in Reaxys; Japanese journal of pharmacology; vol. 56; (1960); p. 377, View in Reaxys; Poisoning; Toxicology, Symptoms, Treatments, 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970, 2, 73.; vol. 2; (1970); p. 73, View in Reaxys; WOODWARD MG.; Northwest Med.; vol. 56; nb. 3; (1957); p. 321 - 322, View in Reaxys; SINGERMAN A.; Prensa Med. Argent.; vol. 44; nb. 12; (1957); p. 915 - 918, View in Reaxys; COLLINS-DINEEN M.; Ohio Med.; vol. 52; nb. 12; (1956); p. 1304 - 1305, View in Reaxys; Clarke's Analysis of Drugs and Poisons, View in Reaxys; Diamantis W; Kletzkin M; International journal of neuropharmacology; vol. 5; nb. 4; (1966); p. 305 - 310, View in Reaxys; http:// www2.siri.org/msds/tox/f/q104/q544.html, View in Reaxys; http://www.pharmgkb.org/do/serve?objId=PA450377&objCls=Drug#tabview=tab1, View in Reaxys; SEYMOUR L. SHAPIRO; VINCENT A. PARRINO; ELAINE S. ISAACS; LOUIS FREEDMAN; Journal of medicinal chemistry; vol. 5; nb. 1; (1962); p. 69 - 76, View in Reaxys; B. J. LUDWIG; J. F. DOUGLAS; L. S. POWELL; M. MEYER; F. M. BERGER; Journal of medicinal chemistry; vol. 3; nb. 1; (1961); p. 53 - 64, View in Reaxys; B. MELANDER; Journal of medicinal chemistry; vol. 1; nb. 5; (1959); p. 443 - 457, View in Reaxys; M. W. KLOHS; F. KELLER; R. E. WILLIAMS; M. I. TOEKES; G. E. CRONHEIM; Journal of medicinal chemistry; vol. 1; nb. 1; (1959); p. 95 - 103, View in Reaxys; Paul A. J. Janssen; Corn. Van De Westeringh; Anton H. M. Jageneau; Paul J. A. Demoen; Bert K. F. Hermans; Georges H. P. Van Daele; Karel H. L. Schellekens; Cyriel A. M. Van Der Eycken; Carlos J. E. Niemegeers; Journal of medicinal chemistry; vol. 1; nb. 3; (1959); p. 281 - 297, View in Reaxys; de JONGE M; FUNCKE AB; Arch Int Pharmacodyn Ther (1899-1996); vol. 137; nb. 1; (1962); p. 375 - 382, View in Reaxys; Poirier, Agnes; Cascais, Anne-Christine; Bader, Urs; Portmann, Renee; Brun, Marie-Elise; Walter, Isabelle; Hillebrecht, Alexander; Ullah, Mohammed; Funk, Christoph; Drug Metabolism and Disposition; vol. 42; nb. 9; (2014); p. 1411 - 1422, View in Reaxys; Patent; Timothy J. Barberich; US2005/267176; (A1); (2005), View in Reaxys 9 of 49

Comment (Pharmacological Data)

Bioactivities present

Kumar, Manish; Dillon, Glenn H.; European Journal of Pharmacology; vol. 775; (2016); p. 149 - 158, View in Reaxys; Inyang, Mandu; Flowers, Riley; McAvoy, Drew; Dickenson, Eric; Bioresource Technology; vol. 216; (2016); p. 778 - 784, View in Reaxys; Acharya, Pratap Chandra; Vasi, Ruqaiya; Suares, Divya; Journal of

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Chromatography B: Analytical Technologies in the Biomedical and Life Sciences; vol. 1029-1030; (2016); p. 16 - 21, View in Reaxys; Phan, Hop V.; McDonald, James A.; Hai, Faisal I.; Price, William E.; Khan, Stuart J.; Fujioka, Takahiro; Nghiem, Long D.; International Biodeterioration and Biodegradation; vol. 113; (2016); p. 49 - 56, View in Reaxys; Noguera-Oviedo, Katia; Aga, Diana S.; Journal of Hazardous Materials; vol. 316; (2016); p. 242 251, View in Reaxys; Schacherer, Joseph; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 284 - 288, View in Reaxys; Habermann, Nina; Mardin, Balca R.; Yakneen, Sergei; Korbel, Jan O.; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 308 - 313, View in Reaxys; Pan, Qiaowei; Anderson, Jennifer; Bertho, Sylvain; Herpin, Amaury; Wilson, Catherine; Postlethwait, John H.; Schartl, Manfred; Guiguen, Yann; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 258 - 262, View in Reaxys; Burger, Gertraud; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 289 - 295, View in Reaxys; Quintana-Murci, Lluis; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 278 - 283, View in Reaxys; Boichard, Didier; Ducrocq, Vincent; Croiseau, Pascal; Fritz, Sébastien; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 274 - 277, View in Reaxys; Mignerot, Laure; Coelho, Susana M.; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 252 - 257, View in Reaxys; Ehrlich, Stanislav Dusko; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 319 - 323, View in Reaxys; Prunet, Nathanaël; Meyerowitz, Elliot M.; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 240 - 246, View in Reaxys; Grelon, Mathilde; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 247 - 251, View in Reaxys; Panaud, Olivier; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 296 - 299, View in Reaxys; Gayon, Jean; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 225 - 230, View in Reaxys; Dujon, Bernard; Pelletier, Georges; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 223 - 224, View in Reaxys; Koszul, Romain; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 324 - 328, View in Reaxys; Bourgeron, Thomas; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 300 - 307, View in Reaxys 10 of 49

Comment (Pharmacological Data)

Bioactivities present

Danchin, Antoine; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 329 - 335, View in Reaxys; Fischer, Alain; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 314 - 318, View in Reaxys; Kremer, Antoine; Comptes Rendus - Biologies; vol. 339; nb. 7-8; (2016); p. 263 - 267, View in Reaxys; Mawasi, Hafiz; Bibi, David; Bialer, Meir; Bioorganic and Medicinal Chemistry; vol. 24; nb. 18; (2016); p. 4246 - 4253, View in Reaxys; Wang, Jianlong; Wang, Shizong; Journal of Environmental Management; vol. 182; (2016); p. 620 - 640, View in Reaxys 11 of 49

Comment (Pharmacological Data)

physiological behaviour discussed

Kumar, Manish; Dillon, Glenn H.; European Journal of Pharmacology; vol. 775; (2016); p. 149 - 158, View in Reaxys 12 of 49

Comment (Pharmacological Data)

physiological behaviour discussed

Poirier, Agnes; Cascais, Anne-Christine; Bader, Urs; Portmann, Renee; Brun, Marie-Elise; Walter, Isabelle; Hillebrecht, Alexander; Ullah, Mohammed; Funk, Christoph; Drug Metabolism and Disposition; vol. 42; nb. 9; (2014); p. 1411 - 1422, View in Reaxys 13 of 49

Effect (Pharmacological Data)

antiepileptic

Species or Test-System (Pharmacological Data)

Swiss-Webster mouse

Sex

male

Route of Application

intraperitoneal

Further Details (Pharmacological Data)

maximal electroshock seizure test

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

127 mg/kg

Kung, Ching-Hsin; Kwon, Chul-Hoon; Medicinal Chemistry Research; vol. 19; nb. 5; (2010); p. 498 - 513, View in Reaxys 14 of 49

Effect (Pharmacological Data)

antiepileptic

Species or Test-System (Pharmacological Data)

Swiss-Webster mouse

Sex

male

Route of Application

intraperitoneal

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Further Details (Pharmacological Data)

subcutaneous pentylenetetrazole seizure threshold test

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

66 mg/kg

Kung, Ching-Hsin; Kwon, Chul-Hoon; Medicinal Chemistry Research; vol. 19; nb. 5; (2010); p. 498 - 513, View in Reaxys 15 of 49

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

fatty acid amide hydrolase of human

Concentration (Pharmacological Data)

1 μmol/l

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

-5.33 percent

Location

supporting information

Vincent, Fabien; Nguyen, Margaret T.; Emerling, Daniel E.; Kelly, Michael G.; Duncton, Matthew A.J.; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 23; (2009); p. 6793 - 6796, View in Reaxys 16 of 49

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

fatty acid amide hydrolase of human

Concentration (Pharmacological Data)

1 μmol/l

Results

molecular target: fatty acid amide hydrolase

Location

supporting information

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

MCF-7 cell membranes expressing human sigma1 receptor

Method (Pharmacological Data)

radioligand binding assay; incubation with title comp. and <3H>-(+)-pentazocine (1 nM) for 180 min at 37 deg C, pH 8.0; filter-bound radioactivity quantified by liquid scintillation counting; nonspecific binding defined by haloperidol or BD1063

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

> 100,000 nmol/l

Lee, Ivan T.; Chen, Shiuhwei; Schetz, John A.; European Journal of Pharmacology; vol. 578; nb. 2-3; (2008); p. 123 - 136, View in Reaxys 18 of 49

Effect (Pharmacological Data)

transport

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Concentration (Pharmacological Data)

5 - 50 μmol/l

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Method (Pharmacological Data)

rats anesthetized; left internal carotid artery catheterized; perfused with oxygenated KRB contg. title comp., atenolol and antipyrine; 30 s later, sacrificed; brains removed; homogenized; analyzed by HPLC-MS/MS; brain permeability of title comp. detd.

Further Details (Pharmacological Data)

MS/MS: tandem mass spectrometry; KRB: Krebs-Ringer bicarbonate buffer (pH 7.4)

Results

brain permeability of title comp. was 0.32E-3 cm/s; table

Summerfield, Scott G.; Read, Kevin; Begley, David J.; Obradovic, Tanja; Hidalgo, Ismael J.; Coggon, Sara; Lewis, Ann V.; Porter, Rod A.; Jeffrey, Phil; Journal of Pharmacology and Experimental Therapeutics; vol. 322; nb. 1; (2007); p. 205 - 213, View in Reaxys 19 of 49

Effect (Pharmacological Data)

transport

Species or Test-System (Pharmacological Data)

multidrug resistant-Madin-Darby canine kidney type II cells

Concentration (Pharmacological Data)

3 μmol/l

Method (Pharmacological Data)

cells seeded on rat type I collagen-coated polycarbonate membranes in Transwell plates; title comp. added on apical/basolateral side; incub. in presence of elacridar, 37 deg C; 60 min later, sampled from RC; title comp. permeation detd.; Papp calcd.

Further Details (Pharmacological Data)

Papp: passive membrane permeability; RC: receiver compartment; cell system used had a high transepithelial electrical resistance ranging from 1800-1200 Ω cm2

Results

passive membrane permeability of title comp. from apical to basolateral side was 9.3E-6 cm/s; table

Effect (Pharmacological Data)

tissue; binding to

Species or Test-System (Pharmacological Data)

rat brain homogenate

Concentration (Pharmacological Data)

1000 μg/kg

Method (Pharmacological Data)

brain homogenate spiked with title comp.; 100 μl aliquot loaded into equilibrium dialysis plate; dialysis carried out for 5 h at 37 deg C using orbital microplate shaker; samples extracted; analyzed by HPLC-MS/MS; unbound fraction of title comp. detd.

Further Details (Pharmacological Data)

MS/MS: tandem mass spectrometry

Results

unbound fraction of title comp. in brain tissue homogenate was 0.6380; fig., table

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human liver cytosol

Concentration (Pharmacological Data)

50 μmol/l

Kind of Dosing (Pharmacological Data)

DMSO stock; final solvent conc. 1 percent (v/v)

Method (Pharmacological Data)

aldehyde oxidase study; phthalazine (2 μmol/l) preincubated with title comp. at 37 deg C; reaction mixture containing cytosol, EDTA and potassium phosphate buffer (pH 7.4) added; 2.5 min incubation; 1-phthalazinone in filtrate analysed by HPLC-MS

Further Details (Pharmacological Data)

EDTA: ethylenediaminetetraacetic acid

Results

enzyme activity was inhibited to 88 percent

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Obach, R. Scott; Huynh, Phuong; Allen, Mary C.; Beedham, Christine; Journal of Clinical Pharmacology; vol. 44; nb. 1; (2004); p. 7 - 19, View in Reaxys 22 of 49

Comment (Pharmacological Data)

effect on CNS and analgesic activity in mice (test, effect, dose): behaviour depression, score 28, 300 mg/kg, p.o.

Sparatore; Novelli; Farmaco; vol. 52; nb. 8-9; (1997); p. 509 - 521, View in Reaxys 23 of 49

Effect (Pharmacological Data)

membrane currents; inhibition of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat embryonic hippocampal neurones

Concentration (Pharmacological Data)

3 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in warm (65-75 deg C) bathing solution with rapid stirring

Method (Pharmacological Data)

neurones were incubated at room temp., pH 7.4; single-channel outside-out patch clamp at -80 mV; addition of 2 μmol/l GABA in presence of title comp.; burst duration of GABAactivated single-channel currents was assayed

Further Details (Pharmacological Data)

medium was supplemented with tetrodotoxin and strychnine (both 1 μmol/l); control: without title comp.; GABA: γ-aminobutiric acid

Results

title comp. prolonged burst duration of single channel-currents; unitary currents exhibited flickering, suggesting channel block (figure, table)

Rho, Jong M.; Donevan, Sean D.; Rogawski, Michael A.; Journal of Pharmacology and Experimental Therapeutics; vol. 280; nb. 3; (1997); p. 1383 - 1391, View in Reaxys 24 of 49

Effect (Pharmacological Data)

membrane currents; inhibition of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat embryonic hippocampal neurones

Concentration (Pharmacological Data)

1E-05 - 0.01 mol/l

Kind of Dosing (Pharmacological Data)

dissolved in warm (65-75 deg C) bathing solution with rapid stirring

Method (Pharmacological Data)

neurones were incubated at room temp., pH 7.4; whole-cell patch clamp at -60 mV; addition of 10 μmol/l NMDA and 10 μmol/l glycine in presence of title comp.; NMDA-activated inward membrane currents was assayed

Further Details (Pharmacological Data)

medium was supplemented with tetrodotoxin and strychnine (both 1 μmol/l); control: without title comp.; NMDA: N-methyl-D-aspartate

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

4 mmol/l

Rho, Jong M.; Donevan, Sean D.; Rogawski, Michael A.; Journal of Pharmacology and Experimental Therapeutics; vol. 280; nb. 3; (1997); p. 1383 - 1391, View in Reaxys 25 of 49

Effect (Pharmacological Data)

membrane currents; induction of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat embryonic hippocampal neurones

Concentration (Pharmacological Data)

0.3 - 10 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in warm (65-75 deg C) bathing solution with rapid stirring

Method (Pharmacological Data)

neurones were incubated at room temp., pH 7.4; whole-cell patch clamp at -60 mV; application of title comp. alone or in presence of GABA (1 μmol/l) ; basal and GABA-induced membrane currents was assayed

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Further Details (Pharmacological Data)

control: without title comp.; medium was supplemented with tetrodotoxin and strychnine (both 1 μmol/l); GABA: γ-aminobutyric acid

Results

title comp. concentration-dependently induced inward currents; title comp. potentiated inward currents elicited by GABA (EC50=2.4 mmol/l); at higher concentrations title comp. blocked GABAA receptors (IC50=12.6 mmol/l) (figure)

Rho, Jong M.; Donevan, Sean D.; Rogawski, Michael A.; Journal of Pharmacology and Experimental Therapeutics; vol. 280; nb. 3; (1997); p. 1383 - 1391, View in Reaxys 26 of 49

Effect (Pharmacological Data)

membrane currents; induction of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat embryonic hippocampal neurones

Concentration (Pharmacological Data)

10 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in warm (65-75 deg C) bathing solution with rapid stirring

Method (Pharmacological Data)

neurones were incubated at room temp. (pH 7.4) with tetrodotoxin and strychnine (both 1 μmol/l); whole-cell patch clamp at -40 mV; effect of title comp. applied to medium on membrane currents was assayed

Further Details (Pharmacological Data)

control: without title comp.; further investigations using various levels of holding potential from -40 to +60 mV, or various (33-148 mmol/l) external Cl(1-) concentration, or γ-aminobutiric acid receptor (GABAA) antagonists

Results

title comp. induced inward currents; effect of title comp. was reversed by changing holding potential to positive; equilibrium potential depended on external Cl(1-) concentration; effect of title comp. was inhibited by GABAA receptor blockers (figure)

Rho, Jong M.; Donevan, Sean D.; Rogawski, Michael A.; Journal of Pharmacology and Experimental Therapeutics; vol. 280; nb. 3; (1997); p. 1383 - 1391, View in Reaxys 27 of 49

Effect (Pharmacological Data)

membrane currents; effect on

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat embryonic hippocampal neurones

Concentration (Pharmacological Data)

10 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in warm (65-75 deg C) bathing solution with rapid stirring

Method (Pharmacological Data)

neurones were incubated at room temp., pH 7.4; whole-cell patch clamp at -60 mV; addition of 1-3 μmol/l GABA in presence of title comp.; deactivation time constants of GABAactivated currents was assayed

Further Details (Pharmacological Data)

medium was supplemented with tetrodotoxin and strychnine (both 1 μmol/l); control: without title comp.; GABA: γ-aminobutiric acid

Results

title comp. prolonged by more than 2.5 fold mean deactivation time (figure)

Rho, Jong M.; Donevan, Sean D.; Rogawski, Michael A.; Journal of Pharmacology and Experimental Therapeutics; vol. 280; nb. 3; (1997); p. 1383 - 1391, View in Reaxys 28 of 49

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

baboon

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

3.2 - 100 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. blended for 3 min into a volume of 60 ml of a matrix prepared with 1-2 g/l of BIO-Serv Agent K in distilled water flavored with orange-drink powder (52 g/l)

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Method (Pharmacological Data)

four of six baboons trained to discriminate lorazepam (1.8 mg/kg, p.o.); treated with title comp. or vehicle (quinine SO4); post 60 min lever responses counted; generalization and drug-discrimination performance determined

Further Details (Pharmacological Data)

control: without title comp.; baboons: LE, ML, MS, RA, RF (Papio anubis) and LO (Papio cynocephalus); generalization: peak mean percentage of lorazepam-lever responding by 80 percent or more

Comment (Pharmacological Data)

No effect

Ator, Nancy A.; Griffiths, Roland R.; Journal of Pharmacology and Experimental Therapeutics; vol. 282; nb. 3; (1997); p. 1442 - 1457, View in Reaxys 29 of 49

Comment (Pharmacological Data)

amnesic activity and no analgesic activity

Lenegre; Avril; Fromage; Milinkevitch; Porsolt; Arzneimittel-Forschung/Drug Research; vol. 38; nb. 4; (1988); p. 558 - 560, View in Reaxys 30 of 49

Comment (Pharmacological Data)

inhibition of 3H-adenosine acceptance in BKEz7.

Melzig; Teuscher; Pharmazie; vol. 41; nb. 8; (1986); p. 604 - 604, View in Reaxys 31 of 49

Comment (Pharmacological Data)

TD50 = 125 mg/kg (mice)

Brouillette; Grunewald; Journal of Medicinal Chemistry; vol. 27; nb. 2; (1984); p. 202 - 206, View in Reaxys 32 of 49

Comment (Pharmacological Data)

anticinvulsant activity in mice, subcutaneous Metrazol-induced convulsions: ED50 = 31.5 mg/kg, and maximal electroshock-induced convulsions: ED50 = 120 mg/kg

Brouillette; Grunewald; Journal of Medicinal Chemistry; vol. 27; nb. 2; (1984); p. 202 - 206, View in Reaxys 33 of 49

Comment (Pharmacological Data)

pharmacokinetics, healthy male volunteers, 100 mg p.o. or 200 mg p.r. in various formulations in combination with diphenhydramine, acetylsalicylic acid, codeine, pentaerythritol tetranitrate: AUC (0 - infinite) 21.15 - 51.69 μg/ml

Gilbert; Aylott; Sogtrop; Draffian; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 10; (1984); p. 1323 - 1327, View in Reaxys 34 of 49

Comment (Pharmacological Data)

Gilbert; Aylott; Sogtrop; Draffian; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 10; (1984); p. 1323 - 1327, View in Reaxys 35 of 49

Comment (Pharmacological Data)

Gilbert; Aylott; Sogtrop; Draffian; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 10; (1984); p. 1323 - 1327, View in Reaxys 36 of 49

Comment (Pharmacological Data)

potentiation of hypnotic action of chloral (400 mg/kg i.p.) or pentobarbital (45 mg/kg i.p.) at 200 and 300 mg/kg p.o.,respectively, without potentiation of toxicity in white mice (Swiss strain) of either sex

Pham Huu Chanh; Navarro Delmasure Ch.; et al.; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 2; (1984); p. 175 - 181, View in Reaxys 37 of 49

Comment (Pharmacological Data)

LD 50: 686 mg/kg (mice), sedative activity

Vinogradova, V. I.; Yunusov, M. S.; Rezhepov, Zh.; Sadritdinov, F. F.; Pharmaceutical Chemistry Journal; vol. 17; nb. 1; (1983); p. 30 - 31; Khimiko-Farmatsevticheskii Zhurnal; vol. 17; nb. 1; (1983); p. 44 - 45, View in Reaxys 38 of 49

Comment (Pharmacological Data)

inhibition of orientation motility, ED 50 = 168 mg/kg p.o.; male mouse

Hoffmeister; Benz; Heise; et al.; Arzneimittel-Forschung/Drug Research; vol. 32; nb. 4; (1982); p. 347 - 360, View in Reaxys 39 of 49

Comment (Pharmacological Data)

inhibition of induced fighting behavior, ED 50 = 104 mg/kg p.o.; male mouse

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Hoffmeister; Benz; Heise; et al.; Arzneimittel-Forschung/Drug Research; vol. 32; nb. 4; (1982); p. 347 - 360, View in Reaxys 40 of 49

Comment (Pharmacological Data)

potentiation of anaesthesia (hexobarbital 100 mg/kg s.c.) = 79 mg/kg p.o.; male mouse

Hoffmeister; Benz; Heise; et al.; Arzneimittel-Forschung/Drug Research; vol. 32; nb. 4; (1982); p. 347 - 360, View in Reaxys 41 of 49

Comment (Pharmacological Data)

inhibition of the capability of "balance", ED 50 = 73 mg/kg p.o. and of traction ED 50 = 152 mg/kg p.o.; male mouse

Hoffmeister; Benz; Heise; et al.; Arzneimittel-Forschung/Drug Research; vol. 32; nb. 4; (1982); p. 347 - 360, View in Reaxys 42 of 49

Comment (Pharmacological Data)

anticonvulsive effect / pentetrazol-shock, ED 50 = 94 mg/kg p.o. and electro-convulsive shock, ED 50 = 107 mg/kg p.o.; male mouse

Hoffmeister; Benz; Heise; et al.; Arzneimittel-Forschung/Drug Research; vol. 32; nb. 4; (1982); p. 347 - 360, View in Reaxys 43 of 49

Comment (Pharmacological Data)

co-administraion to pentaerythritol mononitrate; pharmacokinetics ib dogs

Gilbert; Aylott; Draffan; Sogtrop; Arzneimittel-Forschung/Drug Research; vol. 32; nb. 5; (1982); p. 571 - 574, View in Reaxys 44 of 49

Comment (Pharmacological Data)

72-h LD50(male mice, p.o.): 1421 mg/kg, 1415 mg/kg (with placebo), 1512 mg/kg <with midazolam (3 mg/kg, i.v.)>; 72-h LD50(female mice, p.o.): 1206 mg/kg, 1377 mg/kg (with placebo), 1196 mg/kg <with midazolam (3 mg/kg, i.v.)>

Pieri; Schaffner; Scherschlicht; Polc; Sepinwall; Davidson; Moehler; Cumin; Da Prada; Burkard; Keller; Mueller; Gerold; Cook; Haefely; Arzneimittel-Forschung/Drug Research; vol. 31; nb. 12 a; (1981); p. 2180 - 2201, View in Reaxys 45 of 49

Comment (Pharmacological Data)

pharmacokinetics after oral application in human spittle and serum

Muehlenbruch; Winkler; Archiv der Pharmazie; vol. 314; nb. 7; (1981); p. 646 - 648, View in Reaxys 46 of 49

Comment (Pharmacological Data)

in vitro inhibition of <3H>diazepam binding assay in rats cortex

Albright, J. D.; Moran, D. B.; Wright, W. B.; Collins, J. B.; Beer, B.; et al.; Journal of Medicinal Chemistry; vol. 24; nb. 5; (1981); p. 592 - 600, View in Reaxys 47 of 49

Comment (Pharmacological Data)

time required to fall asleep 68 min, duration of sleeping 7.03 h , heart rate 76.79 beats/ min, P.A.syst 112.41mm Hg, P.A.diast 69.92 mm Hg (patients, 250 mg, p.o.)

du Cailar; Cadi; Jullien; Griffe; Arzneimittel-Forschung; vol. 31; nb. 12 a; (1981); p. 2239 - 2243, View in Reaxys 48 of 49

Comment (Pharmacological Data)

serum concentration data (humans)

Debruyne; Moulin; Camsonne; Bigot; Journal of Pharmaceutical Sciences; vol. 69; nb. 7; (1980); p. 835 - 838, View in Reaxys 49 of 49

Comment (Pharmacological Data)

Table II

Moffett,R.B. et al.; Journal of Medicinal Chemistry; vol. 14; (1971); p. 963 - 968, View in Reaxys Use (2) Use Pattern

References

Tranquilizer

Patent; Summers, Neena L.; McWherter, Charles A.; Feng, Yiqing; US2006/172932; (2006); (A1) English, View in Reaxys

Muscle relaxant

Patent; UNIVERSITY OF MANITOBA; WO2006/130982; (2006); (A1) English, View in Reaxys

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