2-(2,5-dimethoxyphenyl)ethan-1-amine (2C-H) by Asch

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6 substances in Reaxys

2016-04-19 04h:34m:43s (EST)

O NH 2

1. Query

Search as: As drawn

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Reaxys ID 1452583 View in Reaxys

1/6 CAS Registry Number: 3600-86-0 Chemical Name: 2-(2,5-dimethoxy-phenyl)-ethylamine; 2,5-dimethoxyphenylethylamine; 2,5-Dimethoxy phenethylamine; 2,5dimethoxyphenethylamine; 2-(2,5-dimethoxyphenyl)ethanamine; 2-(2,5-dimethoxyphenyl)ethylamine; (2,5-dimethoxyphenyl)ethylamine Linear Structure Formula: C10H15NO2 Molecular Formula: C10H15NO2 Molecular Weight: 181.235 Type of Substance: isocyclic InChI Key: WNCUVUUEJZEATP-UHFFFAOYSA-N Note:

O NH 2

Substance Label (16) Label References 3

Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys

2C-H

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo; British journal of pharmacology; vol. 136; nb. 4; (2002); p. 510 - 519, View in Reaxys; Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys; Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.; Journal of Pharmacology and Experimental Therapeutics; vol. 321; nb. 3; (2007); p. 1054 - 1061, View in Reaxys; Tirapegui, Cristian; Toro-Sazo, Miguel A.; Cassels, Bruce K.; Journal of the Chilean Chemical Society; vol. 59; nb. 3; (2014); p. 2625 - 2627, View in Reaxys

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys

Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p. 3074 - 3084, View in Reaxys; Goode, David R.; Totten, Ryan K.; Heeres, James T.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 51; nb. 8; (2008); p. 2346 - 2349, View in Reaxys

Dothager, Robin S.; Putt, Karson S.; Allen, Brittany J.; Leslie, Benjamin J.; Nesterenko, Vitaliy; Hergenrother, Paul J.; Journal of the American Chemical Society; vol. 127; nb. 24; (2005); p. 8686 - 8696, View in Reaxys

starting in 8.4.

Genady, Afaf R.; El-Zaria, Mohamed E.; Gabel, Detlef; Journal of Organometallic Chemistry; vol. 689; nb. 20; (2004); p. 3242 - 3250, View in Reaxys

Tietze, Lutz F.; Rackelmann, Nils; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 59; nb. 4; (2004); p. 468 - 477, View in Reaxys

Koike, Takeshi; Takeuchi, Naoki; Chemical and Pharmaceutical Bulletin; vol. 50; nb. 4; (2002); p. 484 488, View in Reaxys

Rangisetty; Dukat; Dowd; Herrick-Davis; DuPre; Gadepalli; Teitler; Kelley; Sharif; Glennon; Journal of Medicinal Chemistry; vol. 44; nb. 20; (2001); p. 3283 - 3291, View in Reaxys

Pegurier, C.Ecile; Curtet, Sophie; Nicolas, Jean-Paul; Boutin, Jean A.; Delagrange, Philippe; Renard, Pierre; Langlois, Michel; Bioorganic and Medicinal Chemistry; vol. 8; nb. 1; (2000); p. 163 - 171, View in Reaxys

amine, column 4

Shao, Hui; Zhang, Qiang; Goodnow, Robert; Chen, Li; Tam, Steve; Tetrahedron Letters; vol. 41; nb. 22; (2000); p. 4257 - 4260, View in Reaxys

Koike, Takeshi; Takeuchi, Naoki; Tobinaga, Seisho; Chemical and Pharmaceutical Bulletin; vol. 47; nb. 1; (1999); p. 128 - 130, View in Reaxys

Boger, Dale L.; Chai, Wenying; Ozer, Rachel S.; Andersson, Carl-Magnus; Bioorganic and Medicinal Chemistry Letters; vol. 7; nb. 4; (1997); p. 463 - 468, View in Reaxys; Boger, Dale L.; Chai, Wenying; Tetrahedron; vol. 54; nb. 16; (1998); p. 3955 - 3970, View in Reaxys

Boger, Dale L.; Goldberg, Joel; Jiang, Weiqin; Chai, Wenying; Ducray, Pierre; Lee, Jae Kyoo; Ozer, Rachel S.; Andersson, Carl-Magnus; Bioorganic and Medicinal Chemistry; vol. 6; nb. 8; (1998); p. 1347 1378, View in Reaxys; Boger, Dale L.; Ducray, Pierre; Chai, Wenying; Jiang, Weiqin; Goldberg, Joel; Bioorganic and Medicinal Chemistry Letters; vol. 8; nb. 17; (1998); p. 2339 - 2344, View in Reaxys

Shen, Shuren; Bremont, Beatrice; Serraz, Isabelle; Andrieux, Jean; Poncet, Annie; Mathe-Allainmat, Monique; Chanut, Evelyne; Trouvin, Jean-Hugues; Langlois, Michel; European Journal of Pharmacology; vol. 307; nb. 2; (1996); p. 133 - 140, View in Reaxys

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2,5-diMeOC6H3CH2C H2NH2

Goodwin; Ruthven; Sandler; Xenobiotica; vol. 24; nb. 2; (1994); p. 129 - 141, View in Reaxys

Patent-Specific Data (3) Prophetic ComLocation in Patent References pound Page/Page column

Patent; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; US2015/38366; (2015); (A1) English, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; EP2835648; (2015); (A1) English, View in Reaxys

Claim

Patent; Cytovia, Inc.; US6462041; (2002); (B1) English, View in Reaxys

prophetic product

Patent; Syntex (U.S.A.) Inc.; US5231181; (1993); (A1) English, View in Reaxys

Derivative (3) Comment (Derivative)

References

HCl: 1H-NMR; IR spektrum; UV

Bailey; Legault; Verner; Journal - Association of Official Analytical Chemists; vol. 57; nb. 1; (1974); p. 70 78, View in Reaxys

HCl: B.: Verb.I, Pd/C, H2, Reduktion; F: 138-140grad

Wagner et al.; Synthetic Communications; vol. 1; (1971); p. 47, View in Reaxys

HCl-Salz: F: 139grad

Patent; Polaroid Corp.; US3062884; (1955); Chem.Abstr.; vol. 58; nb. 5575d; (1963), View in Reaxys

Boiling Point (6) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

148 - 150

Khafagy,E.Z.; Lambooy,J.P.; Journal of Medicinal Chemistry; vol. 9; (1966); p. 936 940, View in Reaxys

160

Govindachari; Lakshmikantham; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 46; (1957); p. 406,408, View in Reaxys

148

Sugasawa; Shigehara; Chemische Berichte; vol. 74; (1941); p. 459,462, View in Reaxys; Patent; Polaroid Corp.; US3062884; (1955); Chem.Abstr.; vol. 58; nb. 5575d; (1963), View in Reaxys

140

Cromartie; Harley-Mason; Journal of the Chemical Society; (1952); p. 2525, View in Reaxys

100

0.5

Leaf; Neuberger; Biochemical Journal; vol. 43; (1948); p. 606,608; Biochemical Journal; vol. 57; (1954); p. 528, View in Reaxys

150

Buck; Journal of the American Chemical Society; vol. 54; (1932); p. 3661,3662, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5399

Buck; Journal of the American Chemical Society; vol. 54; (1932); p. 3661,3662, View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.0889

Reference Temperature [°C]

Measurement Temperature [°C]

Buck; Journal of the American Chemical Society; vol. 54; (1932); p. 3661,3662, View in Reaxys Association (MCS) (6) 1 of 6

Description (Association Stability constant of the complex with ... (MCS))

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Solvent (Association (MCS))

H2O; various solvent(s)

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

alpha-cyclodextrin

Rekharsky, Mikhail V.; Goldberg, Robert N.; Schwarz, Frederick P.; Tewari, Yadu B.; Ross, Philip D.; Yamashoji, Yuko; Inoue, Yoshihisa; Journal of the American Chemical Society; vol. 117; nb. 34; (1995); p. 8830 - 8840, View in Reaxys 2 of 6

Description (Association Enthalpy of association (MCS)) Solvent (Association (MCS))

H2O; various solvent(s)

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

alpha-cyclodextrin

Description (Association Further physical properties of the complex (MCS)) Solvent (Association (MCS))

H2O; various solvent(s)

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

alpha-cyclodextrin

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

H2O; various solvent(s)

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

cycloheptaamylose

Description (Association Enthalpy of association (MCS)) Solvent (Association (MCS))

H2O; various solvent(s)

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

cycloheptaamylose

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6 of 6

Description (Association Further physical properties of the complex (MCS)) Solvent (Association (MCS))

H2O; various solvent(s)

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

cycloheptaamylose

Bailey, Keith; Legault, Donald; Organic Magnetic Resonance; vol. 21; nb. 6; (1983); p. 391 - 396, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties light-brown

Montgomery; Buon; Eibauer; Guiry; Keenan; McBean; British Journal of Pharmacology; vol. 152; nb. 7; (2007); p. 1121 - 1130, View in Reaxys

Further Information (2) Description (Fur- References ther Information) Further information

Bailey; Legault; Verner; Journal - Association of Official Analytical Chemists; vol. 57; nb. 1; (1974); p. 70 78, View in Reaxys

Further information

Wagner et al.; Synthetic Communications; vol. 1; (1971); p. 47, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Cheng; Castagnoli Jr.; Journal of Medicinal Chemistry; vol. 27; nb. 4; (1984); p. 513 - 520, View in Reaxys 2 of 2

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Bailey, Keith; Legault, Donald; Organic Magnetic Resonance; vol. 21; nb. 6; (1983); p. 391 - 396, View in Reaxys Pharmacological Data (10) 1 of 10

Comment (Pharmacological Data)

Bioactivities present

Khafagy,E.Z.; Lambooy,J.P.; Journal of Medicinal Chemistry; vol. 9; (1966); p. 936 - 940, View in Reaxys; Glennon; Liebowitz; Mack; Journal of Medicinal Chemistry; vol. 21; nb. 8; (1978); p. 822 - 825, View in Reaxys; Patent; Cytovia, Inc.; US6462041; (2002); (B1) English, View in Reaxys; Patent; Roche Diagnostics Corporation; US6525200; (2003); (B1) English, View in Reaxys; Patent; UNIVERSITY COLLEGE LONDON; WO1999/64861; (1999); (A3), View in Reaxys; Patent; ONO PHARMACEUTICAL CO., LTD.; EP1533294; (2005); (A1) English, View in Reaxys; Patent; ASTRAZENECA AB; WO2005/61484; (2005); (A1) English, View in Reaxys; Phillips; Journal of the American Chemical Society; vol. 75; (1953); p. 3621, View in Reaxys; Buck; Journal of the American Chemical Society; vol. 56; (1934); p. 1607, View in Reaxys; Sugasawa; Shigehara; Chemische Berichte; vol. 74; (1941); p. 459,462, View in Reaxys; Cromartie; Harley-Mason; Journal of the Chemical Society; (1952); p. 2525, View in Reaxys; Phillips; Journal of the American Chemical Society; vol. 75; (1953); p. 3521, View in Reaxys; Baltzly et al.; Journal of the American Chemical Society; vol. 72; (1950); p. 382, View in Reaxys; Buck; Journal of the

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American Chemical Society; vol. 54; (1932); p. 3661,3662, View in Reaxys; Leaf; Neuberger; Biochemical Journal; vol. 43; (1948); p. 606,608; Biochemical Journal; vol. 57; (1954); p. 528, View in Reaxys; Govindachari; Lakshmikantham; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 46; (1957); p. 406,408, View in Reaxys; Baltzly; Buck; Journal of the American Chemical Society; vol. 62; (1940); p. 160,162, View in Reaxys; Wagner et al.; Synthetic Communications; vol. 1; (1971); p. 47, View in Reaxys; Bailey; Legault; Verner; Journal - Association of Official Analytical Chemists; vol. 57; nb. 1; (1974); p. 70 - 78, View in Reaxys; Patent; Polaroid Corp.; US3062884; (1955); Chem.Abstr.; vol. 58; nb. 5575d; (1963), View in Reaxys; Copp, Frederick C.; Franzmann, Karl W.; Grundy, Julian; Whalley, W. Basil; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2455 - 2462, View in Reaxys; Croisy-Delcey, Martine; Huel, Christianne; Bisagni, Emile; Journal of Heterocyclic Chemistry; vol. 25; nb. 2; (1988); p. 655 - 660, View in Reaxys; DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G.; Journal of Medicinal Chemistry; vol. 24; nb. 12; (1981); p. 1432 - 1437, View in Reaxys; Kubo, Akinori; Saito, Naoki; Kawakami, Nanko; Matsuyama, Yasuo; Miwa, Teruyo; Synthesis; nb. 9; (1987); p. 824 - 827, View in Reaxys; Glennon; Liebowitz; Anderson III; Journal of Medicinal Chemistry; vol. 23; nb. 3; (1980); p. 294 - 299, View in Reaxys; Heberer, H.; Kersting, H.; Matschiner, H.; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 3; (1985); p. 487 - 504, View in Reaxys; Cheng; Castagnoli Jr.; Journal of Medicinal Chemistry; vol. 27; nb. 4; (1984); p. 513 - 520, View in Reaxys; Freeman, Jeremiah P.; Fettes-Fields, Mary Kay; Heterocycles; vol. 23; nb. 5; (1985); p. 1073 - 1076, View in Reaxys; Bailey, Keith; Legault, Donald; Organic Magnetic Resonance; vol. 21; nb. 6; (1983); p. 391 - 396, View in Reaxys; Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis; Journal of Medicinal Chemistry; vol. 37; nb. 13; (1994); p. 1929 - 1935, View in Reaxys; Langlois, Michel; Bremont, Beatrice; Shen, Shuren; Poncet, Annie; Andrieux, Jean; et al.; Journal of Medicinal Chemistry; vol. 38; nb. 12; (1995); p. 2050 - 2060, View in Reaxys; Rekharsky, Mikhail V.; Goldberg, Robert N.; Schwarz, Frederick P.; Tewari, Yadu B.; Ross, Philip D.; Yamashoji, Yuko; Inoue, Yoshihisa; Journal of the American Chemical Society; vol. 117; nb. 34; (1995); p. 8830 - 8840, View in Reaxys; Bell; Cantrell; Hogberg; Jaskunas; Johansson; Jordan; Kinnick; Lind; Morin Jr.; Noreen; Oberg; Palkowitz; Parrish; Pranc; Sahlberg; Ternansky; Vasileff; Vrang; West; et al.; Journal of Medicinal Chemistry; vol. 38; nb. 25; (1995); p. 4929 - 4936, View in Reaxys; Cantrell, Amanda S.; Engelhardt, Per; Hoegberg, Marita; Jaskunas, S. Richard; Johansson, Nils Gunnar; Jordan, Christopher L.; Kangasmetsae, Jussi; Kinnick, Michael D.; Lind, Peter; Morin Jr., John M.; Muesing; Noreen, Rolf; Oeberg, Bo; Pranc, Paul; Sahlberg, Christer; Ternansky, Robert J.; Vasileff, Robert T.; Vrang, Lotta; West, Sarah J.; Zhang, Hong; Journal of Medicinal Chemistry; vol. 39; nb. 21; (1996); p. 4261 - 4274, View in Reaxys; Boger, Dale L.; Ozer, Rachel S.; Andersson, Carl-Magnus; Bioorganic and Medicinal Chemistry Letters; vol. 7; nb. 14; (1997); p. 1903 1908, View in Reaxys; Boger, Dale L.; Chai, Wenying; Ozer, Rachel S.; Andersson, Carl-Magnus; Bioorganic and Medicinal Chemistry Letters; vol. 7; nb. 4; (1997); p. 463 - 468, View in Reaxys; Boger, Dale L.; Chai, Wenying; Tetrahedron; vol. 54; nb. 16; (1998); p. 3955 - 3970, View in Reaxys; Boger, Dale L.; Goldberg, Joel; Jiang, Weiqin; Chai, Wenying; Ducray, Pierre; Lee, Jae Kyoo; Ozer, Rachel S.; Andersson, Carl-Magnus; Bioorganic and Medicinal Chemistry; vol. 6; nb. 8; (1998); p. 1347 - 1378, View in Reaxys; Koike, Takeshi; Takeuchi, Naoki; Tobinaga, Seisho; Chemical and Pharmaceutical Bulletin; vol. 47; nb. 1; (1999); p. 128 - 130, View in Reaxys; Goodwin; Ruthven; Sandler; Xenobiotica; vol. 24; nb. 2; (1994); p. 129 - 141, View in Reaxys; Pegurier, C.Ecile; Curtet, Sophie; Nicolas, Jean-Paul; Boutin, Jean A.; Delagrange, Philippe; Renard, Pierre; Langlois, Michel; Bioorganic and Medicinal Chemistry; vol. 8; nb. 1; (2000); p. 163 - 171, View in Reaxys; Shao, Hui; Zhang, Qiang; Goodnow, Robert; Chen, Li; Tam, Steve; Tetrahedron Letters; vol. 41; nb. 22; (2000); p. 4257 - 4260, View in Reaxys; Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p. 3074 - 3084, View in Reaxys; Shen, Shuren; Bremont, Beatrice; Serraz, Isabelle; Andrieux, Jean; Poncet, Annie; Mathe-Allainmat, Monique; Chanut, Evelyne; Trouvin, Jean-Hugues; Langlois, Michel; European Journal of Pharmacology; vol. 307; nb. 2; (1996); p. 133 - 140, View in Reaxys; Boger, Dale L.; Ducray, Pierre; Chai, Wenying; Jiang, Weiqin; Goldberg, Joel; Bioorganic and Medicinal Chemistry Letters; vol. 8; nb. 17; (1998); p. 2339 - 2344, View in Reaxys; Rangisetty; Dukat; Dowd; Herrick-Davis; DuPre; Gadepalli; Teitler; Kelley; Sharif; Glennon; Journal of Medicinal Chemistry; vol. 44; nb. 20; (2001); p. 3283 - 3291, View in Reaxys; Koike, Takeshi; Takeuchi, Naoki; Chemical and Pharmaceutical Bulletin; vol. 50; nb. 4; (2002); p. 484 - 488, View in Reaxys; Venkatachalam; Qazi; Samuel; Uckun; Bioorganic and Medicinal Chemistry; vol. 11; nb. 6; (2003); p. 1095 - 1105, View in Reaxys; Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo; British journal of pharmacology; vol. 136; nb. 4; (2002); p. 510 - 519, View in Reaxys; Blattes, Estelle; Fleury, Maurice-Bernard; Largeron, Martine; Journal of Organic Chemistry; vol. 69; nb. 3; (2004); p. 882 - 890, View in Reaxys; Genady, Afaf R.; El-Zaria, Mohamed E.; Gabel, Detlef; Journal of Organometallic Chemistry; vol. 689; nb. 20; (2004); p. 3242 - 3250, View in Reaxys; Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys; Tao, Houchao; Hwang, Inkyu; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 24; (2004); p. 5979 - 5981, View in Reaxys; Tietze, Lutz F.; Rackelmann, Nils; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 59; nb. 4; (2004); p. 468 - 477, View in Reaxys; Venkatachalam; Uckun, Faith M.; Synthetic Communications; vol. 35; nb. 15; (2005); p. 2039 - 2056, View in Reaxys; Dothager, Robin S.; Putt, Karson S.; Allen, Brittany J.; Leslie, Benjamin J.; Nesterenko, Vitaliy; Hergenrother, Paul J.; Journal of the American Chemical Society; vol. 127; nb. 24; (2005); p. 8686 - 8696, View in Reaxys; Szczepankiewicz, Bruce G.; Kosogof, Christi; Nelson, Lissa T. J.; Liu, Gang; Liu, Bo; Zhao, Hongyu; Serby, Michael D.; Xin, Zhili; Liu, Mei; Gum, Rebecca J.; Haasch, Deanna L.; Wang, Sanyi; Clampit, Jill E.; Johnson, Eric F.; Lubben, Thomas H.; Stashko, Michael A.; Olejniczak, Edward T.; Sun, Chaohong; Dorwin, Sarah A.; Haskins, Kristi; Abad-Zapatero, Cele; Fry, Elizabeth H.; Hutchins, Charles W.; Sham, Hing L.; Rondinone, Cristina M.; Trevillyan, James M.; Journal of Medicinal Chemistry; vol. 49; nb. 12; (2006); p. 3563 - 3580, View in Reaxys; Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.; Journal of Pharmacology and Experimental Therapeutics; vol. 321; nb. 3; (2007); p. 1054 - 1061, View in Reaxys; Montgomery; Buon; Eiba-

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uer; Guiry; Keenan; McBean; British Journal of Pharmacology; vol. 152; nb. 7; (2007); p. 1121 - 1130, View in Reaxys; Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys; Patent; Syntex (U.S.A.) Inc.; US5231181; (1993); (A1) English, View in Reaxys; Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys; Goode, David R.; Totten, Ryan K.; Heeres, James T.; Hergenrother, Paul J.; Journal of Medicinal Chemistry; vol. 51; nb. 8; (2008); p. 2346 - 2349, View in Reaxys; Patent; Anderson, David; Beutel, Bruce; Bosse, Todd D.; Clark, Richard; Cooper, Curt; Dandliker, Peter; David, Caroline; Gu, Yu-Gui; Hansen, Todd Matthew; Hinman, Mira; Kalvin, Douglas; Larson, Daniel P.; Lynch, Linda; Ma, Zhenkun; Motter, Christopher; Palazzo, Fabio; Rosenberg, Teresa; Rehm, Tamara; Sanders, William; Tufano, Michael; Wagner, Rolf; Weitzberg, Moshe; Yong, Hong; Zhang, Tianyuan; US2003/232818; (2003); (A1) English, View in Reaxys; Patent; ELI LILLY AND COMPANY; WO2004/789; (2003); (A1) English, View in Reaxys; Patent; Astellas Pharma Inc.; EP2149560; (2010); (A1) English, View in Reaxys; Marugan, Juan J.; Zheng, Wei; Motabar, Omid; Southall, Noel; Goldin, Ehud; Sidransky, Ellen; Aungst, Ronald A.; Liu, Ke; Sadhukhan, Subir Kumar; Austin, Christopher P.; European Journal of Medicinal Chemistry; vol. 45; nb. 5; (2010); p. 1880 - 1897, View in Reaxys; Patent; KALYPSYS, INC.; WO2006/63294; (2006); (A2) English, View in Reaxys; Patent; Laboratoires Fournier S.A.; US2007/99960; (2007); (A1) English, View in Reaxys; Afon'kin; Kostrikin; Shumeiko; Popov; Russian Journal of Organic Chemistry; vol. 47; nb. 5; (2011); p. 731 - 745, View in Reaxys; Selvakumar, Jayaraman; Ramanathan, Chinnasamy Ramaraj; Organic and Biomolecular Chemistry; vol. 9; nb. 22; (2011); p. 7643 - 7646, View in Reaxys; Wang, Jin-Liang; Zhang, Jun; Zhou, Zhi-Ming; Li, Zhi-Huai; Xue, Wei-Zhe; Xu, Di; Hao, Li-Ping; Han, Xiao-Feng; Fei, Fan; Liu, Ting; Liang, Ai-Hua; European Journal of Medicinal Chemistry; vol. 49; (2012); p. 183 - 190, View in Reaxys; Zhang, Jun; Wang, Jin-Liang; Zhou, Zhi-Ming; Li, Zhi-Huai; Xue, WeiZhe; Xu, Di; Hao, Li-Ping; Han, Xiao-Feng; Fei, Fan; Liu, Ting; Liang, Ai-Hua; Bioorganic and Medicinal Chemistry; vol. 20; nb. 14; (2012); p. 4208 - 4216, View in Reaxys; Islas-Jacome, Alejandro; Cardenas-Galindo, Luis E.; Jerezano, Alberto V.; Tamariz, Joaquin; Gonzalez-Zamora, Eduardo; Gamez-Montano, Rocio; Synlett; vol. 23; nb. 20; (2012); p. 2951 - 2956, View in Reaxys; Benington; Morin; Journal of medicinal chemistry; vol. 11; nb. 4; (1968); p. 896 - 897, View in Reaxys; Macchia; Manera; Martinotti; Necetti; Orlandini; Rossello; Scatizzi; European Journal of Medicinal Chemistry; vol. 30; nb. 11; (1995); p. 869 - 880, View in Reaxys; Saez; Borges; Gonzalez; Cassels; General Pharmacology; vol. 25; nb. 1; (1994); p. 211 - 216, View in Reaxys; Glennon; Ismaiel; Chaurasia; Titeler; Drug Development Research; vol. 22; nb. 1; (1991); p. 25 - 36, View in Reaxys; DeMarinis; Bryan; Shah; Hieble; Pendleton; Journal of Medicinal Chemistry; vol. 24; nb. 12; (1981); p. 1432 - 1437, View in Reaxys; SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL; Chemical reviews; vol. 83; nb. 6; (1983); p. 633 - 649, View in Reaxys; B Macchia; M Macchia; C Manera; E Martinotti; S Nencetti; E Orlandini; A Rossello; R Scatizzi; European journal of medicinal chemistry; vol. 30; (1995); p. 869 - 880, View in Reaxys; Suryavanshi, Padmakar A.; Sridharan, Vellaisamy; Maiti, Swarupananda; Menendez, J. Carlos; Chemistry - A European Journal; vol. 20; nb. 28; (2014); p. 8791 - 8799, View in Reaxys; Li, Zhenyu; Jia, Lejiao; Wang, Jifeng; Wu, Xingkang; Shi, Guowei; Lu, Chunhua; Shen, Yuemao; Chemical Biology and Drug Design; vol. 85; nb. 2; (2015); p. 181 - 188, View in Reaxys; Tirapegui, Cristian; Toro-Sazo, Miguel A.; Cassels, Bruce K.; Journal of the Chilean Chemical Society; vol. 59; nb. 3; (2014); p. 2625 - 2627, View in Reaxys; Patent; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; US2015/38366; (2015); (A1) English, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; EP2835648; (2015); (A1) English, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 2 of 10

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

RD-HGA16 cells expressing human TAAR 1 receptor

Method (Pharmacological Data)

hTAAR1 activation assay; title comp. incubated with test cells in presence of Calcium 3 dye as fluorescent substrate (HAM's F-12 medium, 10percent FBS, 5percent CO2/95percent air, 37 deg C, 1 h); title comp. effect on internal calcium mobilization assessed; fluorimetry

Further Details (Pharmacological Data)

hTAAR1: human trace amine receptor 1; Emax: maximal title comp. efficacy

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2010 nmol/l

Results

title comp. exhibited Emax 69percent

Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella; Bioorganic and Medicinal Chemistry; vol. 16; nb. 15; (2008); p. 7415 - 7423, View in Reaxys 3 of 10

Effect (Pharmacological Data)

partial agonist

Species or Test-System (Pharmacological Data)

CHO-1C19 cells expressing human 5-HT2A receptors

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Method (Pharmacological Data)

cells in serum-free medium labeled with 1 μCi/ml myo-<3H>inositol 24 h and with 0.1 μCi/ml <3H>AA 4 h at 37 deg C; then treated 10 min with title comp.; dose-response curve for total IP accumulation and AA release calculated

Further Details (Pharmacological Data)

control: vehicle; AA: arachidonic acid; IP: inositol phosphate; CHO: Chinese hamster ovary; data expressed as percent of maximal response to 5-HT; 5-HT: serotonin; PLA2 and PLC: phospholipase A2 and phospholipase C, resp.; RE: relative efficacy

Results

title comp. behaved as very weak partial agonist for PLC-mediated IP response (RE = ca. 2percent) but elicited no PLA2-mediated AA release (figures, table)

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.; Journal of Pharmacology and Experimental Therapeutics; vol. 321; nb. 3; (2007); p. 1054 - 1061, View in Reaxys 4 of 10

Effect (Pharmacological Data)

partial agonist

Species or Test-System (Pharmacological Data)

CHO-1C19 cells expressing human 5-HT2C receptors

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Results

title comp. behaved as weak partial agonist for PLC-mediated IP response (RE = ca. 15percent) but elicited no PLA2-mediated AA release in 5-HT2C receptors (figures, table)

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

NIH-3T3 cell membranes expressing rat 5-HT2A receptor

Method (Pharmacological Data)

in vitro; radioligand binding assay; 0.5 nmol/l <3H>ketanserin used as radioligand; assay buffer, pH 7.4; 37 deg C; incubated for 30 min; liquid scintillation counting; nonspecific binding determined with 10 μmol/l ketanserin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2820 nmol/l

Rangisetty; Dukat; Dowd; Herrick-Davis; DuPre; Gadepalli; Teitler; Kelley; Sharif; Glennon; Journal of Medicinal Chemistry; vol. 44; nb. 20; (2001); p. 3283 - 3291, View in Reaxys 6 of 10

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

A-9 cell membranes expressing rat 5-HT2C receptor

Method (Pharmacological Data)

in vitro; radioligand binding assay; 2.0 nmol/l <3H>mesulergine used as radioligand; assay buffer, pH 7.4; 37 deg C; incubated for 30 min; liquid scintillation counting; nonspecific binding determined with 1 μmol/l mesulergine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

6400 nmol/l

Rangisetty; Dukat; Dowd; Herrick-Davis; DuPre; Gadepalli; Teitler; Kelley; Sharif; Glennon; Journal of Medicinal Chemistry; vol. 44; nb. 20; (2001); p. 3283 - 3291, View in Reaxys 7 of 10

Effect (Pharmacological Data)

receptor; binding activity

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Species or Test-System (Pharmacological Data)

NIH-3T3 cell membranes expressing rat 5-HT2A receptors

Kind of Dosing (Pharmacological Data)

as hydrochloride

Method (Pharmacological Data)

in vitro; radioligand competition binding assay; 0.5 nmol/l <3H>ketanserin used as radioligand; binding buffer, pH 7.4; 37 deg C; incubated for 30 min; liquid scintillation counting; nonspecific binding determined using 10 μmol/l ketanserin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3000 nmol/l

Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p. 3074 - 3084, View in Reaxys 8 of 10

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

A-9 cell membranes expressing rat 5-HT2C receptors

Kind of Dosing (Pharmacological Data)

as hydrochloride salt

Method (Pharmacological Data)

in vitro; radioligand competition binding assay; 2.0 nmol/l <3H>mesulegrine used as radioligand; binding buffer, pH 7.4; 37 deg C; incubated for 30 min; liquid scintillation counting; nonspecific binding determined using 1 μmol/l mesulegrine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

5520 nmol/l

Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon; Journal of Medicinal Chemistry; vol. 43; nb. 16; (2000); p. 3074 - 3084, View in Reaxys 9 of 10

Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

white Wistar rat

Sex

female

Route of Application

intraperitoneal

Exposure Period (Pharmacological Data)

24 h

Method (Pharmacological Data)

in vivo

Further Details (Pharmacological Data)

body weight: 150-200 g; no food; water ab libitium

Results

metabolites in urine: corr. phenylacetic acid: 25 percent, fully O-de-Me corr. phenylacetic acid: 1.2 percent, 3-methoxytyramine: 0.8 percent; unchanged amine: 2.2 (mean value; prior to assay, conj. metabolites were hydrolyzed)

Goodwin; Ruthven; Sandler; Xenobiotica; vol. 24; nb. 2; (1994); p. 129 - 141, View in Reaxys 10 of 10

Comment (Pharmacological Data)

in vitro (isolated rabbit ear artery) α1-adrenergic agonist activity (EC50=1.1*10-5 M)

DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G.; Journal of Medicinal Chemistry; vol. 24; nb. 12; (1981); p. 1432 - 1437, View in Reaxys Ecotoxicology (3) 1 of 3

Effect (Ecotoxicology)

antagonist

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

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Concentration (Ecotoxicology)

Ca. 1E-09 - 0.0001 mol/l

Kind of Dosing (Ecotoxi- used as hydrochloride salt; dissolved in Barth's solution cology) Method (Ecotoxicology)

cultured cells expressing rat 5-HT2A receptors voltage-clamped at membrane potential of -70 mV; cells superfused with title comp. preapplied for 2 min prior to challenge with 100 nmol/l of 5-HT; 5-HT-evoked currents recorded

Further Details (Ecotoxi- 5-HT: 5-hydroxytryptamine cology) Type (Ecotoxicology)

pIC50

Value of Type (Ecotoxicology)

4.75 dimensionless

Results

title comp. behaved as 5-HT2A receptor antagonist; it reversibly and concentration-dependently blocked 5-HT-evoked currents (figure, table)

Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 2 of 3

Effect (Ecotoxicology)

membrane current; effect on

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Kind of Dosing (Ecotoxi- used as hydrochloride; 6 - 7 concentrations were applied cology) Method (Ecotoxicology)

oocytes expressing rat 5-HT2A receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; addition of increasing concentrations of title comp. for 10 s; stimulation of membrane currents was determined

Further Details (Ecotoxi- 5-HT: serotonin cology) Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

> 10000 nmol/l

Results

title comp. was almost ineffective (table)

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; HuidobroToro, J Pablo; British journal of pharmacology; vol. 136; nb. 4; (2002); p. 510 - 519, View in Reaxys 3 of 3

Effect (Ecotoxicology)

membrane current; induction of

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Kind of Dosing (Ecotoxi- used as hydrochloride; 6-7 concentrations were applied cology) Method (Ecotoxicology)

oocytes expressing rat 5-HT2C receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; addition of increasing concentrations of title comp. for 10 s; stimulation of membrane currents was determined

Further Details (Ecotoxi- 5-HT: serotonin; Imax: maximal current relative to that evoked by 5-HT cology) Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

3967 nmol/l

Results

Imax = 76 percent

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Reaxys ID 3714171 View in Reaxys

2/6 CAS Registry Number: 3166-74-3 Chemical Name: 2,5-dimethoxyphenethylamine hydrochloride; 2,5-dimethoxy-phenethylamine; hydrochloride; 2,5-Dimethoxyphenaethylamin; Hydrochlorid Linear Structure Formula: C10H15NO2*ClH Molecular Formula: C10H15NO2*ClH Molecular Weight: 217.696 Type of Substance: isocyclic InChI Key: PJMQBIMLDBAWRK-UHFFFAOYSA-N Note:

O NH 2 Cl

Substance Label (3) Label References 25H

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys

PEA 5b*HCl

Macchia, B.; Macchia, M.; Manera, C.; Martinotti, E.; Nancetti, S.; et al.; European Journal of Medicinal Chemistry; vol. 30; nb. 11; (1995); p. 869 - 880, View in Reaxys

2,5-DMPEA*HCl

Bailey, Keith; Legault, Donald; Organic Magnetic Resonance; vol. 21; nb. 6; (1983); p. 391 - 396, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

142 - 143

Solvent (Melting Point)

ethanol

Leaf; Neuberger; Biochemical Journal; vol. 43; (1948); p. 606,608; Biochemical Journal; vol. 57; (1954); p. 528, View in Reaxys 2 of 2

Melting Point [°C]

139

Sugasawa; Shigehara; Chemische Berichte; vol. 74; (1941); p. 459,462, View in Reaxys; Baltzly; Buck; Journal of the American Chemical Society; vol. 62; (1940); p. 164,166; Journal of the American Chemical Society; vol. 64; (1942); p. 3040, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

13C

Solvents (NMR Spectro- D2O scopy) Bailey, Keith; Legault, Donald; Organic Magnetic Resonance; vol. 21; nb. 6; (1983); p. 391 - 396, View in Reaxys Pharmacological Data (7) 1 of 7

Comment (Pharmacological Data)

Bioactivities present

Glennon; Liebowitz; Mack; Journal of Medicinal Chemistry; vol. 21; nb. 8; (1978); p. 822 - 825, View in Reaxys; Sugasawa; Shigehara; Chemische Berichte; vol. 74; (1941); p. 459,462, View in Reaxys; Leaf; Neuberger; Biochemical Journal; vol. 43; (1948); p. 606,608; Biochemical Journal; vol. 57; (1954); p. 528, View in Reaxys; Clark et al.; J. Med. Chem.; vol. 8; (1965); p. 353, View in Reaxys; Baltzly; Buck; Journal of the American Chemical Society; vol. 62; (1940); p. 164,166; Journal of the American Chemical Society; vol. 64; (1942); p. 3040, View in Reaxys; Bailey, Keith; Legault, Donald; Organic Magnetic Resonance; vol. 21; nb. 6; (1983); p. 391 - 396, View in Reaxys; Macchia, B.; Macchia, M.; Manera, C.; Martinotti, E.; Nancetti, S.; et al.; European Journal of Medicinal Chemistry; vol. 30; nb. 11; (1995); p. 869 - 880, View in Reaxys; Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys; Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 1200, View in Reaxys; Huang, Xi-Ping; Setola, Vincent; Yadav, Prem N.; Allen, John A.; Rogan, Sarah C.; Hanson, Bonnie J.; Revankar, Chetana; Robers, Matt; Doucette, Chris; Roth, Bryan L.; Molecular Pharmacology; vol. 76; nb. 4; (2009); p. 710 - 722, View in Reaxys; Daly; Creveling; Witkop; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 273 - 280, View in Reaxys 2 of 7

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

NIH-3T3 cell membranes expressing rat 5-HT2A receptor

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Method (Pharmacological Data)

competition binding assay for ability of title comp. to displace (+/-)-<125I>-DOI ((+/-)<125I>-4-iodo-2,5-dimethoxyphenylisopropylamine; 0.25 nmol/l)

Further Details (Pharmacological Data)

5-HT: 5-hydroxytryptamine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

227 nmol/l

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys 3 of 7

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

NIH-3T3 cells expressing rat 5-HT2A receptor

Method (Pharmacological Data)

title comp. ability to stimulate hydrolysis of radiolabeled phosphatidylinositides assessed by measurement of radiolabeled inositol phosphate accumulation in cells

Further Details (Pharmacological Data)

5-HT: 5-hydroxytryptamine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

12877 nmol/l

Results

intrinsic activity was 82 percent

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys 4 of 7

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay for ability of title comp. to displace (+/-)-<125I>-DOI ((+/-)<125I>-4-iodo-2,5-dimethoxyphenylisopropylamine; 0.25 nmol/l)

Further Details (Pharmacological Data)

HEK: human embryonic kidney; positive control: 5-hydroxytryptamine (5-HT), Ki value of 4.84 nmol/l

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

377 nmol/l

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys 5 of 7

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay for ability of title comp. to displace <3H>ketanserin (10 nmol/l)

Further Details (Pharmacological Data)

HEK: human embryonic kidney; positive control: 5-hydroxytryptamine (5-HT), Ki value of 77.6 nmol/l

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1999 nmol/l

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys

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6 of 7

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

HEK-293 cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

title comp. ability to stimulate hydrolysis of radiolabeled phosphatidylinositides assessed by measurement of radiolabeled inositol phosphate accumulation in cells

Further Details (Pharmacological Data)

HEK: human embryonic kidney; positive control: 5-hydroxytryptamine (5-HT), EC50 value of 5.17 nmol/l

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

1021 nmol/l

Results

intrinsic activity was 96 percent

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.; Molecular Pharmacology; vol. 70; nb. 6; (2006); p. 1956 - 1964, View in Reaxys 7 of 7

Comment (Pharmacological Data)

α-adrenoceptor agonistic activity on isolated guinea-pig ileum (α2); intrinsic activity

Macchia, B.; Macchia, M.; Manera, C.; Martinotti, E.; Nancetti, S.; et al.; European Journal of Medicinal Chemistry; vol. 30; nb. 11; (1995); p. 869 - 880, View in Reaxys

Reaxys ID 3866148 View in Reaxys

3/6 CAS Registry Number: 108774-13-6 Chemical Name: 2,5-dimethoxy-phenethylamine; picrate; 2,5Dimethoxy-phenaethylamin; Picrat Linear Structure Formula: C10H15NO2*C6H3N3O7 Molecular Formula: C6H3N3O7*C10H15NO2 Molecular Weight: 410.34 Type of Substance: isocyclic InChI Key: AXORMOWWFDSRKG-UHFFFAOYSA-N Note:

O O

NH 2

O HO

N O

Melting Point (1) 1 of 1

Melting Point [°C]

166.5 - 167.5

Djerassi et al.; Journal of Organic Chemistry; vol. 21; (1956); p. 975,977, View in Reaxys

Reaxys ID 11306106 View in Reaxys 2

4/6

Chemical Name: 2-(2,5-di([2H3]methoxy)phenyl)ethylamine; 2,5-di([2H3]methoxy)phenethylamine Linear Structure Formula: C10H9 (2)H6NO2 Molecular Formula: C10H15NO2 Molecular Weight: 187.187 InChI Key: WNCUVUUEJZEATP-WFGJKAKNSA-N Note:

O NH 2

2 2H

Substance Label (1) Label References 5

Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys

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Reaxys ID 11306107 View in Reaxys 2H 2H

5/6

Chemical Name: 2,5-di([2H3]methoxy)phenethylamine hydrochloride Linear Structure Formula: C10H9 (2)H6NO2*HCl Molecular Formula: C10H15NO2*ClH Molecular Weight: 223.648 InChI Key: PJMQBIMLDBAWRK-TXHXQZCNSA-N Note:

O NH 2 HCl 2H

O 2H

NMR Spectroscopy (3) 1 of 3

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

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

300

Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

300

Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys 3 of 3

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

13C

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

75.5

Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; fast atom bombardment (FAB)

Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys

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Reaxys ID 26969025 View in Reaxys

6/6 Chemical Name: 2,5-dimethoxy-[13C6]-phenethylamine hydrochloride Linear Structure Formula: C4 (13)C6H15NO2*ClH Molecular Formula: C10H15NO2*ClH Molecular Weight: 223.63 InChI Key: PJMQBIMLDBAWRK-WJPZTKJYSA-N Note:

O H 13C

13C

H 13C 13 13CH C

NH 2

HCl

Substance Label (1) Label References 4a

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

136.5 - 137.3

Solvent (Melting Point)

isopropyl alcohol; ethanol

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

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

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelmass spectrome- led Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387, View in Reaxys try (HRMS); spectrum

15/15

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