9,10-didehydro-N,N-diethyl-6-methylergoline-8β-carboxamide (LSD) [CAS 50-37-3; InChIKey VAYOS by Asch

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Date

14 substances in Reaxys

2016-03-05 01h:20m:29s (EST)

1. Query

N HN

N H

Search as: As drawn

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Reaxys ID 94179 View in Reaxys

1/14 CAS Registry Number: 50-37-3 Chemical Name: 9,10-didehydro-N,N-diethyl-6-methylergoline-8β-carboxamide; [3H]-LSD; d-LSD; LSD; lysergic acid diethylamide; [3H]-LSD; lysergide Linear Structure Formula: C20H25N3O Molecular Formula: C20H25N3O Molecular Weight: 323.438 Type of Substance: heterocyclic InChI Key: VAYOSLLFUXYJDT-RDTXWAMCSA-N Note:

O N

HN H

Substance Label (8) Label References LSD

Pineyro; Deveault; De Montigny; Blier; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 351; nb. 2; (1995); p. 119 - 125, View in Reaxys; Nakahara; Takahashi; Kikura; Biological and Pharmaceutical Bulletin; vol. 18; nb. 9; (1995); p. 1223 - 1227, View in Reaxys; Parker, Matthew A.; Marona-Lewicka, Danuta; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 41; nb. 26; (1998); p. 5148 - 5149, View in Reaxys; Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 - 3134, View in Reaxys; Patent; TEMPLE UNIVERSITY - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; CANNEY, Daniel, J.; BHANDARE, Richie, R.; BLASS, Benjamin, E.; ABOU-GHARBIA, Magid; WO2014/85413; (2014); (A1) English, View in Reaxys

Patent; Zhang, Fang-Jie; Liu, Hshiou-ting; US2006/223998; (2006); (A1) English, View in Reaxys

Merck 5665

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys; Haddjeri, Nasser; De Montigny, Claude; Curet, Olivier; Blier, Pierre; European Journal of Pharmacology; vol. 343; nb. 2-3; (1998); p. 179 - 192, View in Reaxys

D-LSD

Schechter, Martin D.; European Journal of Pharmacology; vol. 341; nb. 2-3; (1998); p. 131 - 134, View in Reaxys

LSD, Merck I., 5665

Watkins, Clare J.; Newberry, Nigel R.; British Journal of Pharmacology; vol. 117; nb. 1; (1996); p. 21 - 28, View in Reaxys

M 5665

Zgombick, John M.; Schechter, Lee E.; Adham, Nika; Kucharewicz, Stefan A.; Weinshank, Richard L.; Branchek, Theresa A.; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 354; nb. 3; (1996); p. 226 236, View in Reaxys

MERCK 5665

Carter; Champney; Hwang; Eglen; European Journal of Pharmacology; vol. 280; nb. 3; (1995); p. 243 - 250, View in Reaxys

LSD (Merck 5507) Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.; Medicinal Chemistry Research; vol. 5; nb. 9; (1995); p. 651 - 663, View in Reaxys Patent-Specific Data (1) Location in Patent References Claim

Patent; Vivus, Inc.; US6037346; (2000); (A1) English, View in Reaxys; Patent; Halikas; James A.; US5102913; (1992); (A1) English, View in Reaxys; Patent; Tam, Peter; Gesundheit, Neil; Wilson, Leland F.; US2002/161016; (2002); (A1) English, View in Reaxys; Patent; Research Foundation of the State University of New York; US5696125; (1997); (A1) English, View in Reaxys; Patent; Bio-Development Limited; EP496839; (1996); (B1) German, View in Reaxys; Patent; NexMed (Holdings), Inc.; US2002/45665; (2002); (A1) English, View in Reaxys; Patent; The Regents of the University of Minnesota; US5028611; (1991); (A1) English, View in Reaxys

Derivative (5) Comment (Deriva- Derivative tive)

References

C23H22O5S*C20 Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak ChemH25N3O ical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys C21H18O5S*C20 Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak ChemH25N3O ical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys 2-[[3-Bromo-2,5dimethyl-4-oxocyclohexa-2,5-dien-(E)-ylidene](3-bromo-4-hydroxy-2,5-dimethyl-phenyl)-meth-

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

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yl]-benzenesulfonic acid; compound with (6aR, 9R)-7-methyl-4,6,6a,7,8,9hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid diethylamide C20H25N3O*C16 Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak ChemH11N2O4S(1-)*N ical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys a(1+) Lg-tartrate (mp: 198-200 degree ; <alpha>=30 degree ); Further Data see Handbook (Fluorescence spectrum, Fluorescence maxima)

Stoll; Hofmann; Helvetica Chimica Acta; vol. 38; (1955); p. 421,432, View in Reaxys; Sprince et al.; Science (Washington, DC, United States); vol. 125; (1957); p. 442, View in Reaxys; Buscaino; Ricerca Scientifica; vol. 21; (1951); p. 519,523, View in Reaxys

Melting Point (4) 1 of 4

Melting Point [°C]

82 - 84

Solvent (Melting Point)

benzene

Ishii, Hisashi; Niwaguchi, Tetsukichi; Nakahara, Yuji; Hayashi, Makoto; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 902 - 905, View in Reaxys 2 of 4

Melting Point [°C]

82 - 83

Solvent (Melting Point)

benzene

Nakahara; Niwaguchi; Yakugaku Zasshi; vol. 94; (1974); p. 407,411; Chem.Abstr.; vol. 81; nb. 91772; (1974), View in Reaxys 3 of 4

Melting Point [°C]

Nakahara; Niwaguchi; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 2337,2339-2341, View in Reaxys 4 of 4

Melting Point [°C]

80 - 85

Solvent (Melting Point)

benzene

Stoll; Hofmann; Helvetica Chimica Acta; vol. 26; (1943); p. 944,947; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 251; (1938); p. 155,160, View in Reaxys Association (MCS) (1) 1 of 1

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

dimethylsulfoxide; aq. phosphate buffer

Temperature (Association (MCS)) [°C]

Partner (Association (MCS))

melanin

Nakahara; Takahashi; Kikura; Biological and Pharmaceutical Bulletin; vol. 18; nb. 9; (1995); p. 1223 - 1227, View in Reaxys Chromatographic Data (1) Chromatographic References data LC (Liquid chromatography)

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman; Rapid Communications in Mass Spectrometry; vol. 27; nb. 15; (2013); p. 1751 - 1762, View in Reaxys

Conformation (1) Object of Investi- References gation

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Conformation

Andrews, Peter R.; Munro, Sharon L. A.; Sadek, Maruse; Wong, Margaret G.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1988); p. 711 - 718, View in Reaxys

Dissociation Exponent (2) 1 of 2

Dissociation Exponent (pK)

7.8

Type (Dissociation Exponent)

a1/apparent

Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc; Environmental Science and Technology; vol. 42; nb. 18; (2008); p. 6809 - 6816, View in Reaxys 2 of 2

Dissociation Exponent (pK)

6.37

Solvent (Dissociation Exponent)

aq. ethanol

Method (Dissociation Exponent)

potentiometric

Type (Dissociation Exponent)

a/apparent

Stoll et al.; Helvetica Chimica Acta; vol. 37; (1954); p. 2039,2051, View in Reaxys Further Information (1) Description (Fur- References ther Information) Further information

Inoue et al.; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 409, View in Reaxys

Optical Rotatory Dispersion (1) References Nakahara; Niwaguchi; Yakugaku Zasshi; vol. 94; (1974); p. 407,411; Chem.Abstr.; vol. 81; nb. 91772; (1974), View in Reaxys; Nakahara; Niwaguchi; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 2337,2339-2341, View in Reaxys Optical Rotatory Power (3) 1 of 3

Patent; Roche Diagnostics Corporation; US6063908; (2000); (A1) English, View in Reaxys

2 of 3

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Nakahara; Niwaguchi; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 2337,2339-2341, View in Reaxys 3 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=0.5

Solvent (Optical Rotatory Power)

pyridine

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Stoll; Hofmann; Helvetica Chimica Acta; vol. 38; (1955); p. 421,432, View in Reaxys Partition octan-1-ol/water (MCS) (1) 1 of 1

log POW

2.95

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Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc; Environmental Science and Technology; vol. 42; nb. 18; (2008); p. 6809 - 6816, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

4000 - 667 cm**(-1)

Troxler; Hofmann; Helvetica Chimica Acta; vol. 40; (1957); p. 1706,1714, View in Reaxys Mass Spectrometry (4) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

tandem mass spectrometry; electrospray ionisation (ESI); high resolution mass spectrometry (HRMS); spectrum

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman; Rapid Communications in Mass Spectrometry; vol. 27; nb. 15; (2013); p. 1751 - 1762, View in Reaxys

electrospray ionisation (ESI); high resolution mass spectrometry (HRMS); spectrum

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman; Rapid Communications in Mass Spectrometry; vol. 27; nb. 15; (2013); p. 1751 - 1762, View in Reaxys

spectrum

collisional activation

Duffin, Kevin L.; Wachs, Timothy; Henion, Jack D.; Analytical Chemistry; vol. 64; nb. 1; (1992); p. 61 - 68, View in Reaxys Inoue et al.; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 409, View in Reaxys; Nakahara; Niwaguchi; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 2337,2339-2341, View in Reaxys

UV/VIS Spectroscopy (3) 1 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Nakahara; Niwaguchi; Yakugaku Zasshi; vol. 94; (1974); p. 407,411; Chem.Abstr.; vol. 81; nb. 91772; (1974), View in Reaxys 2 of 3

Description (UV/VIS Spectroscopy)

UV/VIS

Nakahara; Niwaguchi; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 2337,2339-2341, View in Reaxys 3 of 3

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

ethanol

Comment (UV/VIS Spectroscopy)

210 - 320 nm

Troxler; Hofmann; Helvetica Chimica Acta; vol. 40; (1957); p. 1706,1714, View in Reaxys Fluorescence Spectroscopy (3) Description (Fluo- Solvent (Fluoresrescence Spectro- cence Spectroscopy) scopy)

Comment (FluoReferences rescence Spectroscopy)

Spectrum

aq. methanol

320 - 600 nm; bei 298 K.

Aaron et al.; Clin.chim.Acta; vol. 45; (1973); p. 375,381, View in Reaxys

Maxima

H2O

465 nm; Loesung vom pH 7.

Udenfriend et al.; Journal of Pharmacology and Experimental Therapeutics; vol. 120; (1957); p. 26,29, View in Reaxys

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Maxima

H2O

440 nm; Loesung vom pH 9.

Phosphorescence Spectroscopy (1) Description Solvent (PhosComment (Phos(Phosphoresphorescence phorescence cence SpectroSpectroscopy) Spectroscopy) scopy) Spectrum

aq. methanol

350 - 750 nm; bei 77 K.

Bowman et al.; Science (Washington, DC, United States); vol. 122; (1955); p. 32, View in Reaxys References

Aaron et al.; Clin.chim.Acta; vol. 45; (1973); p. 375,381, View in Reaxys

Pharmacological Data (79) 1 of 79

Comment (Pharmacological Data)

Bioactivities present

Leemann,H.G.; Weller,H.; Helvetica Chimica Acta; vol. 43; (1960); p. 1359 - 1364, View in Reaxys; Jacob III; Anderson III; Meshul; Shulgin; Castagnoli Jr.; Journal of Medicinal Chemistry; vol. 20; nb. 10; (1977); p. 1235 - 1239, View in Reaxys; Patent; Ghoshal, Mitali; Vitone, Stephen; Sigler, Gerald F.; McNally, Alan J.; US2001/44118; (2001); (A1) English, View in Reaxys; Patent; Vivus, Inc.; US6037346; (2000); (A1) English, View in Reaxys; Patent; Roche Diagnostics Corporation; US6063908; (2000); (A1) English, View in Reaxys; Patent; Halikas; James A.; US5102913; (1992); (A1) English, View in Reaxys; Patent; Tam, Peter; Gesundheit, Neil; Wilson, Leland F.; US2002/161016; (2002); (A1) English, View in Reaxys; Patent; Research Foundation of the State University of New York; US5696125; (1997); (A1) English, View in Reaxys; Patent; Synaptic Pharmaceutical Corporation; US2003/166066; (2003); (A1) English, View in Reaxys; Patent; Wyeth; US2004/23970; (2004); (A1) English, View in Reaxys; Patent; Bio-Development Limited; EP496839; (1996); (B1) German, View in Reaxys; Patent; MILES INC.; WO1992/4015; (1992); (A1), View in Reaxys; Patent; Renshaw, Perry F.; Cohen, Bruce M.; US2006/39890; (2006); (A1) English, View in Reaxys; Patent; ABBOTT GMBH and CO.KG; WO2006/40177; (2006); (A1) English, View in Reaxys; Patent; Zhang, Fang-Jie; Liu, Hshiou-ting; US2006/223998; (2006); (A1) English, View in Reaxys; Patent; The Board of Governors for Higher Education the State of Rhode Island and Providence Plantation.; US5863928; (1999); (A1) English, View in Reaxys; Stoll et al.; Helvetica Chimica Acta; vol. 37; (1954); p. 2039,2051, View in Reaxys; Stoll; Petrzilka; Helvetica Chimica Acta; vol. 36; (1953); p. 1137,1141, View in Reaxys; Troxler; Hofmann; Helvetica Chimica Acta; vol. 40; (1957); p. 2160,2169, View in Reaxys; Troxler; Hofmann; Helvetica Chimica Acta; vol. 40; (1957); p. 1706,1714, View in Reaxys; Stoll; Hofmann; Helvetica Chimica Acta; vol. 38; (1955); p. 421,432, View in Reaxys; Stoll; Schlientz; Helvetica Chimica Acta; vol. 38; (1955); p. 585,586, View in Reaxys; Aaron et al.; Clin.chim.Acta; vol. 45; (1973); p. 375,381, View in Reaxys; Sprince et al.; Science (Washington, DC, United States); vol. 125; (1957); p. 442, View in Reaxys; Buscaino; Ricerca Scientifica; vol. 21; (1951); p. 519,523, View in Reaxys; Troxler; Hofmann; Helvetica Chimica Acta; vol. 42; (1959); p. 793,800, View in Reaxys; Hofmann,A.; Die Mutterkornalkaloide <Stuttgart 1964> S.169,170, View in Reaxys; Bowman et al.; Science (Washington, DC, United States); vol. 122; (1955); p. 32, View in Reaxys; Stoll et al.; Org.Synth.Isotopes; (1958); p. 405, View in Reaxys; Stoll et al.; Helvetica Chimica Acta; vol. 37; (1954); p. 820,823, View in Reaxys; Patent; E.Lilly and Co.; US2736728; (1954), View in Reaxys; Patent; E.Lilly and Co.; US2774763; (1955), View in Reaxys; Stoll; Hofmann; Helvetica Chimica Acta; vol. 26; (1943); p. 944,947; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 251; (1938); p. 155,160, View in Reaxys; Freter et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 3191, View in Reaxys; Patent; Sandoz; DE820437; (1951); DRP/DRBP Org.Chem., View in Reaxys; Udenfriend et al.; Journal of Pharmacology and Experimental Therapeutics; vol. 120; (1957); p. 26,29, View in Reaxys; Domelsmith; Munchausen; Houk; Journal of Medicinal Chemistry; vol. 20; nb. 10; (1977); p. 1346 - 1348, View in Reaxys; Inoue et al.; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 409, View in Reaxys; Nakahara; Niwaguchi; Yakugaku Zasshi; vol. 94; (1974); p. 407,411; Chem.Abstr.; vol. 81; nb. 91772; (1974), View in Reaxys; Niwaguchi et al.; Yakugaku Zasshi; vol. 96; (1976); p. 673,674,677, View in Reaxys; Nakahara; Niwaguchi; Chemical and Pharmaceutical Bulletin; vol. 19; (1971); p. 2337,2339-2341, View in Reaxys; Johnson; Frescas; Oberlender; Nichols; Journal of Medicinal Chemistry; vol. 34; nb. 5; (1991); p. 1662 - 1668, View in Reaxys; Ishii, Hisashi; Niwaguchi, Tetsukichi; Nakahara, Yuji; Hayashi, Makoto; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 902 - 905, View in Reaxys; Duffin, Kevin L.; Wachs, Timothy; Henion, Jack D.; Analytical Chemistry; vol. 64; nb. 1; (1992); p. 61 - 68, View in Reaxys; Nelson, Chad C.; Analytical Chemistry; vol. 64; nb. 14; (1992); p. 1578 - 1585, View in Reaxys; Stanovnik, Branko; Tisler, Miha; Jurgec, Milan; Rucman, Rudolf; Heterocycles; vol. 16; nb. 5; (1981); p. 741 - 745, View in Reaxys; Andrews; Craik; Martin; Journal of Medicinal Chemistry; vol. 27; nb. 12; (1984); p. 1648 - 1657, View in Reaxys; Arvidsson; Hacksell; Johansson; Nilsson; Lindberg; Sanchez; Wikstroem; Svensson; Hjorth; Carlsson; Journal of Medicinal Chemistry; vol. 27; nb. 1; (1984); p. 45 - 51, View in Reaxys; Hoffman; Nichols; Journal of Medicinal Chemistry; vol. 28; nb. 9; (1985); p. 1252 - 1255, View in Reaxys; Andrews, Peter R.; Munro, Sharon L. 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Comment (Pharmacological Data)

physiological behaviour discussed

Odagaki, Yuji; Kinoshita, Masakazu; Toyoshima, Ryoichi; European Journal of Pharmacology; vol. 726; nb. 1; (2014); p. 109 - 115, View in Reaxys 3 of 79

Comment (Pharmacological Data)

physiological behaviour discussed

Afzal, Muhammad; Shahid, Muhammad; Mehmood, Zahid; Bukhari, Shazia Anwer; Talpur, Mir Munsif Ali; Asian Journal of Chemistry; vol. 26; nb. 2; (2014); p. 531 - 536, View in Reaxys 4 of 79

Comment (Pharmacological Data)

physiological behaviour discussed

Markiewicz, Bartosz; Sznajdrowska, Agata; Chrzanowski, Lukasz; Lawniczak, Lukasz; Zgola-Grzeskowiak, Agnieszka; Kubiak, Krzysztof; Nawrot, Jan; Pernak, Juliusz; New Journal of Chemistry; vol. 38; nb. 7; (2014); p. 3146 - 3153, View in Reaxys 5 of 79

Effect (Pharmacological Data)

ligand binding; inhibition of

Species or Test-System (Pharmacological Data)

cortex homogenate of C57BL/6 mouse

Further Details (Pharma- radioligand displacement assay; radioligand: 0.39 - 0.47 nM [3H]ketanserin cological Data) Results

molecular target: mouse serotonin 2A receptor

Dougherty, John P.; Aloyo, Vincent J.; Psychopharmacology; vol. 215; nb. 3; (2011); p. 581 - 593, View in Reaxys 6 of 79

Effect (Pharmacological Data)

ligand binding; inhibition of

Species or Test-System (Pharmacological Data)

cortex homogenate of C57BL/6 mouse

Further Details (Pharma- radioligand displacement assay; radioligand: 0.39 - 0.47 nM [3H]ketanserin; inhibition concological Data) stant (Ki); Ki related to: mouse serotonin 2A receptor Type (Pharmacological Data)

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Value of Type (Pharmacological Data)

0.8 nmol/l

Dougherty, John P.; Aloyo, Vincent J.; Psychopharmacology; vol. 215; nb. 3; (2011); p. 581 - 593, View in Reaxys 7 of 79

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cells of Candida albicans

Further Details (Pharma- toxicity of title comp. determined by measuring dehydrogenase activity cological Data) Type (Pharmacological Data)

percent cytotoxicity

Value of Type (Pharmacological Data)

17.2 percent

El-Husseiny, Amel Fawzy; Asian Journal of Chemistry; vol. 22; nb. 1; (2010); p. 603 - 614, View in Reaxys 8 of 79

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cells of Candida fructus

Further Details (Pharma- toxicity of title comp. determined by measuring dehydrogenase activity cological Data) Type (Pharmacological Data)

percent cytotoxicity

Value of Type (Pharmacological Data)

20.2 percent

El-Husseiny, Amel Fawzy; Asian Journal of Chemistry; vol. 22; nb. 1; (2010); p. 603 - 614, View in Reaxys 9 of 79

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cells of Candida glabrata

Further Details (Pharma- toxicity of title comp. determined by measuring dehydrogenase activity cological Data) Type (Pharmacological Data)

percent cytotoxicity

Value of Type (Pharmacological Data)

25.4 percent

El-Husseiny, Amel Fawzy; Asian Journal of Chemistry; vol. 22; nb. 1; (2010); p. 603 - 614, View in Reaxys 10 of 79

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cells of Candida oleophila

Further Details (Pharma- toxicity of title comp. determined by measuring dehydrogenase activity cological Data) Type (Pharmacological Data)

percent cytotoxicity

Value of Type (Pharmacological Data)

9.4 percent

El-Husseiny, Amel Fawzy; Asian Journal of Chemistry; vol. 22; nb. 1; (2010); p. 603 - 614, View in Reaxys 11 of 79

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cells of Candida tropicalis

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Further Details (Pharma- toxicity of title comp. determined by measuring dehydrogenase activity cological Data) Type (Pharmacological Data)

percent cytotoxicity

Value of Type (Pharmacological Data)

12.8 percent

El-Husseiny, Amel Fawzy; Asian Journal of Chemistry; vol. 22; nb. 1; (2010); p. 603 - 614, View in Reaxys 12 of 79

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cells of Candida parapsilosis

Further Details (Pharma- toxicity of title comp. determined by measuring dehydrogenase activity cological Data) Type (Pharmacological Data)

percent cytotoxicity

Value of Type (Pharmacological Data)

9.8 percent

El-Husseiny, Amel Fawzy; Asian Journal of Chemistry; vol. 22; nb. 1; (2010); p. 603 - 614, View in Reaxys 13 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing rat 5-HT6 receptors

Concentration (Pharmacological Data)

Ca. 1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

0.2 nmol/l <35S>GTPγS used as radioligand; 20 mmol/l HEPES buffer (pH 7.4), 1 h; Gα activation determined by Scintillation Proximity Assay/antibody-immunocapture procedure; non-specific binding defined at 10 μmol/l GTPγS

Further Details (Pharma- serotonin (5-HT) used for comparison (pEC50: 7.69; Emax at 1 μmol/l=100percent) cological Data) Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

9.17 dimensionless

Results

title comp. stimulated binding <35S>GTPγS to Gα proteins with Emax=72.2percent, thus acting as partial agonist; fig.

Dupuis, Delphine S.; la Cour, Clotilde Mannoury; Chaput, Christine; Verriele, Laurence; Lavielle, Gilbert; Millan, Mark J.; European Journal of Pharmacology; vol. 588; nb. 2-3; (2008); p. 170 - 177, View in Reaxys 14 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing rat 5-HT6 receptors

Method (Pharmacological Data)

radioligand binding assay; 0.1 nmol/l <125I>SB258,585 used as radioligand; 50 mmol/l Tris (pH 7.4) buffer, 37 deg C, 45 min; non-specific binding defined with 10 μmol/l methiothepin

Further Details (Pharma- 5-HT: serotonin cological Data) Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

8.94 dimensionless

Results

title comp. showed very high affinity for 5-HT6 receptors; table

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15 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay; test cells (Hh2A) incubated with title comp. and <3H>ketanserin as radioligand at 25 deg C for 60 min; scintillation fluid added and radioactivity determined using scintillation counter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3.1 nmol/l

Nichols, David E.; Frescas, Stewart P.; Chemel, Benjamin R.; Rehder, Kenneth S.; Zhong, Desong; Lewin, Anita H.; Bioorganic and Medicinal Chemistry; vol. 16; nb. 11; (2008); p. 6116 - 6123, View in Reaxys 16 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

A549 cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay; test cells (A20) incubated with title comp. and <3H>ketanserin as radioligand at 25 deg C for 60 min; scintillation fluid added and radioactivity determined using scintillation counter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.6 nmol/l

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay; test cells (Hh2A) incubated with title comp. and <3H>INBMeO as radioligand at 25 deg C for 60 min; scintillation fluid added and radioactivity determined using scintillation counter

Further Details (Pharma- <3H>INBmeO: N-(2-<3H>methoxybenzyl)-2-(2-<3H>methoxy-5-methoxy-4-iodophencological Data) yl)ethylamine Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3.5 nmol/l

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

A549 cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay; test cells (A20) incubated with title comp. and <3H>INBMeO as radioligand at 25 deg C for 60 min; scintillation fluid added and radioactivity determined using scintillation counter

Further Details (Pharma- <3H>INBmeO: N-(2-<3H>methoxybenzyl)-2-(2-<3H>methoxy-5-methoxy-4-iodophencological Data) yl)ethylamine Type (Pharmacological Data)

Value of Type (Pharmacological Data)

4.0 nmol/l

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Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.01 - 0.085 mg/kg

Method (Pharmacological Data)

title comp. administered 30 min before 5-min extinction tests; percent responding and response rates on title comp.-appropriate lever determined

Further Details (Pharma- control: saline; percent responding = number of correct responses/total number of responses cological Data) Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

Ca. 0.03 mg/kg

Results

percent of responding to title comp.-appropriate lever was dose-dependent; rate of responding was sign. higher following 0.01 and 0.02 mg/kg of title comp. (figures)

Gresch, Paul J.; Barrett, Robert J.; Sanders-Bush, Elaine; Smith, Randy L.; Journal of Pharmacology and Experimental Therapeutics; vol. 320; nb. 2; (2007); p. 662 - 669, View in Reaxys 20 of 79

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intracerebral

Concentration (Pharmacological Data)

0.1875 - 0.75 μg

Kind of Dosing (Pharma- title comp. was administered dose/side cological Data) Method (Pharmacological Data)

title comp. injected into anterior cingulate cortex (ACC) over 1-min period via bilateral 26gauge guide cannulae implanted surgically; immediately after cannulae replacement percent responding and response rates on title comp.-appropriate lever determined

Further Details (Pharma- control: saline; internal control: artificial cerebrospinal fluid (14percent responding); percent cological Data) responding = number of correct responses/total number of responses Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

0.29 μg

Results

0.1875, 0.375 and 0.75 μg/side of title comp. produced 41, 73.5 and 88.7percent of responding to title comp.-appropriate lever, resp.; response rates did not differ sign. over course of dose-response curve for title comp. (figures)

Gresch, Paul J.; Barrett, Robert J.; Sanders-Bush, Elaine; Smith, Randy L.; Journal of Pharmacology and Experimental Therapeutics; vol. 320; nb. 2; (2007); p. 662 - 669, View in Reaxys 21 of 79

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intracerebral

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Concentration (Pharmacological Data)

0.375 μg

Kind of Dosing (Pharma- title comp. was administered dose/side cological Data) Method (Pharmacological Data)

Further Details (Pharma- control: saline; internal control: artificial cerebrospinal fluid (14percent responding); further cological Data) investigation with M100907, selective 5-HT2A receptor antagonist, administered s.c. 20 min before title comp. injection Results

0.375 μg/side title comp. produced 68percent of responding to title comp.-appropriate lever; s.c. injection of M100907, 5-HT2A receptor antagonist, reduced percent responding to 16percent; effect of M100907 was reversible; response rate did not differ sign. (figures)

Gresch, Paul J.; Barrett, Robert J.; Sanders-Bush, Elaine; Smith, Randy L.; Journal of Pharmacology and Experimental Therapeutics; vol. 320; nb. 2; (2007); p. 662 - 669, View in Reaxys 22 of 79

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.06 mg/kg

Method (Pharmacological Data)

title comp. administered 30 min before 5-min extinction test; percent responding and response rates on title comp.-appropriate lever determined

Further Details (Pharma- control: saline; further investigation with M100907, mianserin, ketanserin, SB206553 and cological Data) WAY-100635, selective serotonin receptor antagonists of different subtypes (injection 45 min prior test) Results

at 0.06 mg/kg title comp. percent of responding to title comp.-appropriate lever was ca. 90percent; M100907, ketanserin and mianserin sign. reduced title comp.-appropriate lever responding in dose-dependent manner; SB206553 and WAY-100635 did not alter it (figure)

Gresch, Paul J.; Barrett, Robert J.; Sanders-Bush, Elaine; Smith, Randy L.; Journal of Pharmacology and Experimental Therapeutics; vol. 320; nb. 2; (2007); p. 662 - 669, View in Reaxys 23 of 79

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.04 mg/kg

Method (Pharmacological Data)

title comp. administered 30 min before 5-min extinction test; percent responding and response rates on title comp.-appropriate lever determined

Further Details (Pharma- control: saline; further investigation with M100907, selective 5-HT2A serotonin receptor ancological Data) tagonists (injection into ACC via bilateral cannulae 20 min prior title comp. administration); ACC: anterior cingulate cortex Results

at 0.04 mg/kg title comp. produced 80percent of title comp.-appropriate lever responding; M100907, selective 5-HT2A receptor antagonist, reduced percent of responding to 12percent; effect of M100907 was reversible; response rates did not differ sign. (figures)

Gresch, Paul J.; Barrett, Robert J.; Sanders-Bush, Elaine; Smith, Randy L.; Journal of Pharmacology and Experimental Therapeutics; vol. 320; nb. 2; (2007); p. 662 - 669, View in Reaxys 24 of 79

Effect (Pharmacological Data)

behavioural symptoms

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Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.06 mg/kg

Method (Pharmacological Data)

title comp. administered 30 min before 5-min extinction test; response rates on title comp.appropriate lever determined

at 0.06 mg/kg title comp. response rate was ca. 25 responses/5 min; M100907, ketanserin, mianserin, SB206553 and WAY-100635 did not sign. alter it (figure)

Gresch, Paul J.; Barrett, Robert J.; Sanders-Bush, Elaine; Smith, Randy L.; Journal of Pharmacology and Experimental Therapeutics; vol. 320; nb. 2; (2007); p. 662 - 669, View in Reaxys 25 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

African green monkey kidney COS-7 cells

Method (Pharmacological Data)

cells expressing human histamine H1 receptor and cotransfected with pNFκ B-Luc incubated with title comp. for 48 h, then assayed for luminescence

Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

< 5 dimensionless

Bakker; Weiner; Ter Laak; Beuming; Zuiderveld; Edelbroek; Hacksell; Timmerman; Brann; Leurs; Molecular Pharmacology; vol. 65; nb. 3; (2004); p. 538 - 549, View in Reaxys 26 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

African green monkey kidney COS-7 cells

Method (Pharmacological Data)

cells expressing human histamine H1 receptor used; homogenates incubated with title comp. for 30 min at 25 deg C in H1-binding buffer in presence of 1 nmol/l <3H>mepyramine; radioactivity determined by liquid scintillation counting

Further Details (Pharma- nonspecific binding determined in presence of 1 μmol/l mianserin cological Data) Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

5.7 dimensionless

Bakker; Weiner; Ter Laak; Beuming; Zuiderveld; Edelbroek; Hacksell; Timmerman; Brann; Leurs; Molecular Pharmacology; vol. 65; nb. 3; (2004); p. 538 - 549, View in Reaxys 27 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Concentration (Pharmacological Data)

1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

competition binding assay; 0.1 nmol/l <125I>-DOI used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer supplemented with 5 mmol/l CaCl2; radioactivity quantified by Packard Topcount plate reader

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Further Details (Pharma- nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); DOI: 1-(2,5-dimecological Data) thoxy-4-iodophenyl)-2-aminopropane; title comp. binding affinity to recombinant 5-HT2A receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

9.12 dimensionless

Results

title comp. displayed extremely high affinity for the 5-HT2A receptor; table

Knight, Antony R.; Misra, Anil; Quirk, Kathleen; Benwell, Karen; Revell, Dean; Kennett, Guy; Bickerdike, Mike; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 370; nb. 2; (2004); p. 114 - 123, View in Reaxys 28 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

CHO-K1 cell membranes expressing human 5-HT2B receptor

Concentration (Pharmacological Data)

1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

competition binding assay; 5 nmol/l <3H>-5-HT used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer supplemented with 4 mmol/l CaCl2; radioactivity quantified by Packard Topcount plate reader

Further Details (Pharma- nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); title comp. binding cological Data) affinity to recombinant 5-HT2B receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

9.01 dimensionless

Results

title comp. displayed high affinity for the 5-HT2B receptor; table

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2C receptor

Concentration (Pharmacological Data)

1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

competition binding assay; 1 nmol/l <3H>-5-HT used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer; radioactivity quantified by Packard Topcount plate reader

Further Details (Pharma- nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); title comp. binding cological Data) affinity to recombinant 5-HT2C receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

8.96 dimensionless

Results

title comp. displayed high affinity for the 5-HT2C receptor; table

Effect (Pharmacological Data)

agonist

Endpoint of Effect (Phar- arachidonic acid (AA) release macological Data)

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Species or Test-System (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

Concentration (Pharmacological Data)

0.0001 - 10 μmol/l

Method (Pharmacological Data)

cells labeled with <3H>AA for 4 h; washed three times with DMEM and incubated with title comp. for 30 min at 37 deg C; <3H>AA in medium counted

Further Details (Pharma- 5-HT = 5-hydroxytryptamine; DMEM = Dulbecco's modified Eagle's medium; control: without cological Data) title comp. Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

20 nmol/l

Results

title comp. stimulated the <3H>AA accumulation conc.-dependently (table)

Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 1; (2003); p. 229 - 237, View in Reaxys 31 of 79

Effect (Pharmacological Data)

agonist

Endpoint of Effect (Phar- IPs accumulation macological Data) Species or Test-System (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

Concentration (Pharmacological Data)

0.001 - 10 μmol/l

Method (Pharmacological Data)

cells loaded with myo-<2-3H(N)>inositol and pretreated with 10 μmol/l pargyline and 10 mmol/l LiCl for 15 min at 37 deg C in CMRL-1066 media; then title comp. added for 30 min; <3H>IPs of cell lysate separated by ion-exchange chromatography and counted

Further Details (Pharma- 5-HT = 5-hydroxytryptamine; IPs = a mixture of inositol mono- bis-, and triphosphate; control: cological Data) without title comp. Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

9.8 nmol/l

Results

title comp. stimulated the <3H>IPs accumulation conc.-dependently (table)

Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 1; (2003); p. 229 - 237, View in Reaxys 32 of 79

Effect (Pharmacological Data)

receptor; binding activity

Endpoint of Effect (Phar- <125I>2,5-dimethoxy-4-iodoamphetamine (DOI) binding macological Data) Species or Test-System (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

Concentration (Pharmacological Data)

1E-05 - 10 μmol/l

Method (Pharmacological Data)

competition binding study; cells incubated with 2E-1 nmol/l <125I>DOI in the presence title comp. for 60 min at 25 deg C in Tris-EDTA buffer, pH 7.4; nonspecific binding determ. with 10 μmol/l cinanserin; filter-bound radioactivity counted

Further Details (Pharma- 5-HT = 5-hydroxytryptamine; control: without title comp. cological Data) Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3.5 nmol/l

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Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.; Journal of Pharmacology and Experimental Therapeutics; vol. 304; nb. 1; (2003); p. 229 - 237, View in Reaxys 33 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

HEK293 cells expressing rTAR1

Concentration (Pharmacological Data)

0.8 μmol/l

Method (Pharmacological Data)

cells incubated in KRH with 100 μmol/l 3-isobutyl-1-methylxanthine and title comp. for 1 h at 37 deg C; cAMP content measured using competitive binding of <3H>cAMP to a cAMPbinding protein

Further Details (Pharma- HEK: human embryonic kidney; rTAR1: rat trace amine receptor 1; reference comp.: forcological Data) skolin; KRH: Krebs-Ringer-HEPES buffer Results

title comp. induced cAMP production acting as agonist (diagram)

Bunzow; Sonders; Arttamangkul; Harrison; Zhang; Quigley; Darland; Suchland; Pasumamula; Kennedy; Olson; Magenis; Amara; Grandy; Molecular Pharmacology; vol. 60; nb. 6; (2001); p. 1181 - 1188, View in Reaxys 34 of 79

Effect (Pharmacological Data)

secretion stimulant

Species or Test-System (Pharmacological Data)

Chinese hamster ovary-K1 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

cells incubated with <3H>myo-inositol for 24 h and <3H>AA for 4 h at 37 deg C, before incubation with title comp. for 10 min; IP accumulation and AA release measured simultaneously

Further Details (Pharma- cells expressing human 5-HT2C-VSV receptors; 5-HT: 5-hydroxytryptamine; VSV: edited recological Data) ceptor containing valine, serine and valine at positions 156, 158 and 160, respectively; AA: arachidonic acid; IP: inositol phosphates Results

maximal effect on stimulation of AA release (relative efficacy): 0.23 (relative to that of 5-HT)

Berg, Kelly A.; Cropper, Jodie D.; Niswender, Colleen M.; Sanders-Bush, Elaine; Emeson, Ronald B.; Clarke, William P.; British Journal of Pharmacology; vol. 134; nb. 2; (2001); p. 386 - 392, View in Reaxys 35 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary-K1 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

cells incubated with <3H>myo-inositol for 24 h and <3H>AA for 4 h at 37 deg C, before incubation with title comp. for 10 min; IP accumulation and AA release measured simultaneously

maximal effect on stimulation of IP accumulation (relative efficacy): 0.07 (relative to that of 5-HT)

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mouse ileum cells membranes

Method (Pharmacological Data)

5-HT7 receptors; title comp. was initially incubated with masking drugs and <3H>mesulergine (10 nmol/l, 25 μl) in phosphate buffer at 37 deg C for 10 min and then 60 min with membrane homogenate; constant of inhibition (Ki) was calculated

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Further Details (Pharma- masking drugs: cinanserin (30 nmol/l), RS 102221 (3 μmol/l), raclopride (1 μmol/l), prazosin cological Data) (0.1 μmol/l), yohimbine (0.1 μmol/l) Results

two site competition with high and low affinity values of pKi (9.4 and 6.6) were obtained; percentage fraction was 86 and 14 percent respectively

Hemedah, Maggie; Coupar, Ian M.; Mitchelson, Fred J.; European Journal of Pharmacology; vol. 387; nb. 3; (2000); p. 265 - 272, View in Reaxys 37 of 79

Effect (Pharmacological Data)

drug dependence

Endpoint of Effect (Phar- 50 percent LSD-lever responding produced macological Data) Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.01 - 0.08 mg/kg

Kind of Dosing (Pharma- as tartrate 30 min before testing cological Data) Method (Pharmacological Data)

in vivo; two-lever drug discrimination assay; (+)-lysergic acid diethylamide (LSD)-trained rats (200-220 g) maintained at 22-24 deg C, 12-h light/dark cycle and 40-50 percent relative humidity with free access to water and rationed amount of supplemental feed

Further Details (Pharma- percent of rats selecting LSD lever ( percent SDL) for eachdose of title comp. determined; cological Data) degree of substitution determined by max. percentADL for all doses of title comp.; no substitution: <= 59 percent SDL; partial substitution: 60-79 percent SDL; complete substitution: > 80 percent SDL Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

0.012 mg/kg

Results

dose (mg/kg)/ percent SDL: 0.01/46, 0.02/78, 0.04/81, 0.08/100 - full substitution

Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 42; nb. 20; (1999); p. 4257 - 4263, View in Reaxys 38 of 79

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

jejunum of Wistar rat

Sex

not specified

Concentration (Pharmacological Data)

10 - 100 nmol/l

Method (Pharmacological Data)

isolated rat jejunum, 3 - 4 cm length; gassed Krebs-Henseleit solution, 37 deg C; incubation with title compd., 40 min later 5-hydroxytryptamine in increasing concn. (-7.5 to -4 log mol/ l) at 10 min intervals; isotonic transducer, contractions measured

Further Details (Pharma- experiment was carried out in the presence of ondansetron (1 μmol/l) - blockade of 5-HT3 cological Data) receptors; control: contraction obtained with acetylcholine (1μmol/l) Results

depression of the maximal response to 5-hydroxytryptamine at 30 nmol/l, dose dependent effect

Hemedah; Coupar; Mitchelson; British journal of pharmacology; vol. 126; nb. 1; (1999); p. 179 - 188, View in Reaxys 39 of 79

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

homogenate of Wistar rat jejunum

Sex

not specified

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Method (Pharmacological Data)

phosphate buffer (50 mmol/l) with <3H>-mesulergine (10 nmol/l) and title comp. (at least 5 different concn., quadruplicate) incubated for 10 min at 37 deg C; homogenate added; incubation 60 min at 37 deg C; filtration; LSC of filter

Further Details (Pharma- 5-HT7 receptor assay; other receptors blocked by masking drugs added prior to first incucological Data) bation: cinanserin (30 nmol/l), RS 102221 (3 μmol/l), raclopride (1 μmol/l), prazosin (0.1 μmol/l), and yohimbine (0.1 μmol/l) Results

apparent pKB = 7.6

Hemedah; Coupar; Mitchelson; British journal of pharmacology; vol. 126; nb. 1; (1999); p. 179 - 188, View in Reaxys 40 of 79

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

homogenate of guinea-pig ileum

Sex

not specified

Kind of Dosing (Pharma- title comp. used in the concn. range of -11 to -7 log mol/l cological Data) Method (Pharmacological Data)

inhibition of <3H>-mesulergine binding (diagram); pKi = 9.4

Hemedah; Coupar; Mitchelson; British journal of pharmacology; vol. 126; nb. 1; (1999); p. 179 - 188, View in Reaxys 41 of 79

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

membranes of Wistar rats whole brain minus cerebellum

Sex

not specified

Kind of Dosing (Pharma- title comp. used in the concn. range ca. -11 to -6 log mol/l cological Data) Method (Pharmacological Data)

homogenized brain, membrane isolated; phosphate buffer (50 mmol/l) with <3H>-mesulergine (10 nmol/l) and title comp. (13 concn., duplicates) incub. for 10 min at 37 deg C; membrane homogenate added; incub. 60 min at 37 deg C; filtration; LSC of filter

inhibition of <3H>-mesulergine binding (diagram); pKi = 8.1

Hemedah; Coupar; Mitchelson; British journal of pharmacology; vol. 126; nb. 1; (1999); p. 179 - 188, View in Reaxys 42 of 79

Comment (Pharmacological Data)

in vivo activity in the two-lever drug discrimination paradigm in rats trained to discriminate saline from LSD tartrate, ED50: 0.037 μmol/kg (0.016 mg/kg)

Monte, Aaron P.; Marona-Lewicka, Danuta; Lewis, Mechelle M.; Mailman, Richard B.; Wainscott, David B.; Nelson, David L.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 41; nb. 12; (1998); p. 2134 - 2145, View in Reaxys 43 of 79

Comment (Pharmacological Data)

in vivo (rats, i.p.) effectivity in drug discrimination assay: ED50=40 nmol/kg (training drug: LSD)

Parker, Matthew A.; Marona-Lewicka, Danuta; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 41; nb. 26; (1998); p. 5148 - 5149, View in Reaxys 44 of 79

Effect (Pharmacological Data)

blocking of 5-hydroxytryptamin-stimulated cAMP concn.

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Species or Test-System (Pharmacological Data)

murine fibroblasts (LMtk-) cell line

Concentration (Pharmacological Data)

<= 10 μmol/l

Exposure Period (Pharmacological Data)

30 min

Method (Pharmacological Data)

cell line membrane preincubated (HEPES-buffered saline, pH 7.4, 37 deg C, 20 min) in presence of title compd., then incubated in presence of 5-hydroxytryptamine (10 min); detn. of intracellular cAMP (radioimmunoassay)

Results

affinity const. Ki = 6.0 nM; apparent dissociation constant Kb = 8.0 nM; no intrinsic activity observed

Adham, Nika; Zgombick, John M.; Bard, Jonathan; Journal of Pharmacology and Experimental Therapeutics; vol. 287; nb. 2; (1998); p. 508 - 514, View in Reaxys 45 of 79

Effect (Pharmacological Data)

binding affinity

Species or Test-System (Pharmacological Data)

murine fibroblasts (LMtk-) cell line

Concentration (Pharmacological Data)

0.5 - 60 nmol/l

Exposure Period (Pharmacological Data)

30 min

Method (Pharmacological Data)

3H-labelled title compd. (76.7 Ci/mmol) used; cell line membrane incubated (37 deg C)

Further Details (Pharma- Kd - equilibrium dissociation const.; Bmax - maximal binding density cological Data) Results

Kd = 4.0 nM; Bmax = 189 fmol/mg protein; binding isotherm given (diagram)

Adham, Nika; Zgombick, John M.; Bard, Jonathan; Journal of Pharmacology and Experimental Therapeutics; vol. 287; nb. 2; (1998); p. 508 - 514, View in Reaxys 46 of 79

Effect (Pharmacological Data)

neuroregulatoric

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

10 μg/kg

Kind of Dosing (Pharma- daily dose via osmotic minipumps for 2 d cological Data) Method (Pharmacological Data)

250-300 g rats (12 h light/dark cycle); extracellular recording of firing rate (FR) of dorsal raphe 5-HT neurons (DR) performed with single barrelled glass micropipettes; without/with 0.75 mg/kg s.c. (-)-pindolol (PIN)

Further Details (Pharma- title comp. effect on DR studied cological Data) Results

DR suppressed (graph; diagram)

Haddjeri, Nasser; De Montigny, Claude; Curet, Olivier; Blier, Pierre; European Journal of Pharmacology; vol. 343; nb. 2-3; (1998); p. 179 - 192, View in Reaxys 47 of 79

Effect (Pharmacological Data)

drug interaction

Species or Test-System (Pharmacological Data)

Fawn-Hooded rats

Sex

male

Route of Application

intraperitoneal

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Concentration (Pharmacological Data)

0.04 mg/kg

Kind of Dosing (Pharma- used as tartrate cological Data) Method (Pharmacological Data)

in vivo; rats trained to discriminate MDMA (1.5 mg/kg); MDMA (0.15 mg/kg) and title comp. injected; number of responses and needed time on MDMA or saline lever analyzed

Further Details (Pharma- MDMA: 3,4-methylenedioxymethamphetamine; experiment was terminated after accumucological Data) lation of 10 responses on one of two levers; control, saline-treated trained rats Results

rats treated with title comp. produced a saline-like response; co-administration MDMA and title comp. synergized; maximal MDMA response; required time to reach 10 responses increased by approximately 522 percent compared to control

Schechter, Martin D.; European Journal of Pharmacology; vol. 341; nb. 2-3; (1998); p. 131 - 134, View in Reaxys 48 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary 1C19 cells

Concentration (Pharmacological Data)

Ca. 3E-10 - 3E-07 mol/l

Method (Pharmacological Data)

ability of title comp. to activate PLC-mediated IP accumulation studied; cells labeled with 1 μCi/ml myo-<3H>inositol (24 h, 37 deg C) incubated with title comp. for 10 min; mono-, di-, triphosphates of inositol separated by ion exchange chromatography

Further Details (Pharma- radioactivity counted by liquid scintillation; cells expressing human 5-HT2C receptors; 5-HT: cological Data) 5-hydroxitryptamine; PLC: phospholipase C; IP: inositol phosphates; 5-HT used asyreference comp. (pEC = 7.43); Emax: maximal response Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

7.80 dimensionless

Results

Emax title comp./Emax 5-HT = 0.17 (table)

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 49 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary 1C19 cells

Concentration (Pharmacological Data)

Ca. 3E-10 - 3E-07 mol/l

Method (Pharmacological Data)

ability of title comp. to activate PLA2-mediated arachidonic acid release studied; cells labeled with 0.1 μCi/ml <14C>arachidonic acid (4 h, 37 deg C) incubated with title comp. for 10 min; radioactivity measured by liquid scintillation counting

Further Details (Pharma- cells expressing human 5-HT2C receptors; 5-HT: 5-hydroxytryptamine; PLA2: phospholipase cological Data) A2; 5-HT used as reference comp. (pEC50 = 7.34); Emax: maximal response Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

8.11 dimensionless

Results

Emax title comp./Emax 5-HT = 0.39 (table)

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 50 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary FA4 cells

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Concentration (Pharmacological Data)

0.3 μmol/l

Method (Pharmacological Data)

Further Details (Pharma- radioactivity counted by liquid scintillation; cells expressing human 5-HT2A receptors; 5-HT: cological Data) 5-hydroxytryptamine; PLC: phospholipase C; IP: inositol phosphates; 5-HT used as reference comp.; Emax: maximal response Results

Emax title comp./Emax 5-HT ca. 0.10 (figure)

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 51 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary FA4 cells

Concentration (Pharmacological Data)

0.3 μmol/l

Method (Pharmacological Data)

Further Details (Pharma- cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; PLA2: phospholipase cological Data) A2; 5-HT used as reference comp.; Emax: maximal response Results

Emax title comp./Emax 5-HT ca. 0.55 (figure)

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 52 of 79

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Chinese hamster ovary FA4 cells

Concentration (Pharmacological Data)

0.3 μmol/l

Method (Pharmacological Data)

ability of title comp. to increase Ca(2+) conc. studied; cells loaded with Fura-2; intracellular Ca(2+) conc. determined by measuring fluorescence (340/380 nm)

Further Details (Pharma- cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; 5-HT used as refercological Data) ence comp.; Emax: maximal response Comment (Pharmacological Data)

No effect

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.; Molecular Pharmacology; vol. 54; nb. 1; (1998); p. 94 - 104, View in Reaxys 53 of 79

Comment (Pharmacological Data)

in vivo drug discrimination: ED50 = 0.040 mmol/kg in LSD-trained male prague-Dawley rats; in vitro affinity at <3H>ketanserin-labeled rat cortical 5-HT2A and <3H>-8-OH-DPAT-labeled rat hippocampal 5-HT1A receptors (male Sprague-Dawley rat)

Monte, Aaron P.; Marona-Lewicka, Danuta; Parker, Matthew A.; Wainscott, David B.; Nelson, David L.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 39; nb. 15; (1996); p. 2953 - 2961, View in Reaxys 54 of 79

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

Dunkin-Hartley guinea-pig, superior cervical ganglion

Sex

male

Concentration (Pharmacological Data)

3 - 30 nmol/l

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Method (Pharmacological Data)

grease-gap technique; animals killed by pentabarbitone i.p. injection; title comp. superfused over the ganglion 15-20 min after 5-hydroxytryptamine (5-HT); concentration-response curve (CRC)

Results

reduced concentration-dependently but not proportionally the depolarization response of 5HT in the presence of granisetron (1 μM)

Watkins, Clare J.; Newberry, Nigel R.; British Journal of Pharmacology; vol. 117; nb. 1; (1996); p. 21 - 28, View in Reaxys 55 of 79

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

Dunkin-Hartley ,guinea-pig superior cervical ganglion

Sex

male

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

grease-gap technique; animals killed by pentabarbitone i.p. injection; title comp. superfused over the ganglion 15-20 min after the last application of 2-methyl-5-hydroxytryptamine (100 and 300 μM)

Comment (Pharmacological Data)

No effect

Watkins, Clare J.; Newberry, Nigel R.; British Journal of Pharmacology; vol. 117; nb. 1; (1996); p. 21 - 28, View in Reaxys 56 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mutant A5.46S 5-HT2C receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharma- Ki: binding affinity cological Data) Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.3 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 57 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

wild-type 5-HT2C receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharma- Ki: binding affinity cological Data) Type (Pharmacological Data)

Value of Type (Pharmacological Data)

6.4 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 58 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

mutant S5.46A 5-HT2A receptors expressed in COS-1 cells

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Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharma- Ki: binding affinity cological Data) Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.1 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 59 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

wild-type 5-HT2A receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharma- Ki: binding affinity cological Data) Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.24 nmol/l

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.; Molecular Pharmacology; vol. 50; nb. 1; (1996); p. 34 - 42, View in Reaxys 60 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

NIH-3T3 fibroblast

Concentration (Pharmacological Data)

0.1 - 50 nmol/l

Method (Pharmacological Data)

recombinant human 5-HT1Dα receptor subtype stably expressed in cells; radioligand binding study with <3H>-labelled title comp.

Further Details (Pharma- equilibrium dissociation constant (Kd) cological Data) Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.1 nmol/l

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Y-1 adrenocortical tumor cells

Concentration (Pharmacological Data)

0.1 - 50 nmol/l

Method (Pharmacological Data)

recombinant human 5-HT1Dβ receptor subtype stably expressed in cells; radioligand binding study with <3H>-labelled title comp.

Further Details (Pharma- equilibrium dissociation constant (Kd) cological Data) Type (Pharmacological Data)

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Value of Type (Pharmacological Data)

4.9 nmol/l

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Y-1 adrenocortical tumor cells

Method (Pharmacological Data)

recombinant human 5-HT1Dβ receptor subtype stably expressed in cells; potency to inhibit forskolin-stimulated cAMP accumulation; radioimmunoassay

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2.9 nmol/l

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

NIH-3T3 fibroblast

Method (Pharmacological Data)

recombinant human 5-HT1Dα receptor subtype stably expressed in fibroblasts; potency to inhibit forskolin-stimulated cAMP accumulation; radioimmunoassay

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2.0 nmol/l

Effect (Pharmacological Data)

neuron stimulant

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat piriform cortical interneurons

Sex

male

Concentration (Pharmacological Data)

3 - 100 nmol/l

Method (Pharmacological Data)

brain slices perfused with normal ACSF with title comp. for 10 min at 34 deg C; extracellular recordings conducted from interneurons (layer III) using glass microelectrodes; firing rates recorded

Further Details (Pharma- 5-hydroxytryptamine (5-HT) as reference comp.; further investigation in presence of 5cological Data) HT2A receptor antagonist MDL 100,907; ACSF: artificial cerebrospinal fluid Results

title comp. induced concentration-dependent increase in firing rate of almost every cell excited by 5-HT; maximal excitation achieved by 100 nmol/l title comp. was 39 percent of effect of 100 μmol/l 5-HT; effect was mediated by 5-HT2A receptors (figure)

Marek, Gerard J.; Aghajanian, George K.; Journal of Pharmacology and Experimental Therapeutics; vol. 278; nb. 3; (1996); p. 1373 - 1382, View in Reaxys 65 of 79

Effect (Pharmacological Data)

neuron stimulant

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat piriform cortical interneurons

Sex

male

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Concentration (Pharmacological Data)

3 - 100 nmol/l

Method (Pharmacological Data)

brain slices perfused with normal ACSF with title comp. for 10 min at 34 deg C before treatment with 5-HT, or NE, or AMPA; extracellular recordings conducted from interneurons (layer III) using glass microelectrodes; firing rates recorded

Further Details (Pharma- 5-HT: 5-hydroxytryptamine; NE: norepinephrine; AMPA: α-amino-3-hydroxy-5-methyl-4-isocological Data) xazolepropionate; ACSF: artificial cerebrospinal fluid Results

100 nmol/l title comp. substantially blocked 5-HT-induced excitation of interneurons but not effect of 100 μmol/l NE; 10 and 100 nmol/l title comp. increased excitatory effect of AMPA to 202 percent and 344 percent, respectively (figure, table)

Marek, Gerard J.; Aghajanian, George K.; Journal of Pharmacology and Experimental Therapeutics; vol. 278; nb. 3; (1996); p. 1373 - 1382, View in Reaxys 66 of 79

Comment (Pharmacological Data)

the ability to displace <3H>-8-hydroxy-2-(di-n-propylamio)tetralin from rat hippocamal homogenate and <3H>ketanserin from rat cortex homogenate

Monte, Aaron P.; Marona-Lewicka, Danuta; Kanthasamy, Arthi; Sanders-Bush, Elaine; Nichols, David E.; Journal of Medicinal Chemistry; vol. 38; nb. 6; (1995); p. 958 - 966, View in Reaxys 67 of 79

Comment (Pharmacological Data)

in vivo potency in producing the LSD-like discriminative stimulus effect in rats trained to discriminate 0.08 mg/kg LSD tartrate from saline ED50=48 nmol/kg

Monte, Aaron P.; Marona-Lewicka, Danuta; Kanthasamy, Arthi; Sanders-Bush, Elaine; Nichols, David E.; Journal of Medicinal Chemistry; vol. 38; nb. 6; (1995); p. 958 - 966, View in Reaxys 68 of 79

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

Dunkin-Hartley guinea-pig ileum

Sex

male

Method (Pharmacological Data)

250-350 g pigs killed, ileal segments suspended in Krebs solution + (μM) cocaine 10, corticosterone 10, pargyline 5, indomethacin, atropine 1 at 37 deg C, pH 7.4

Further Details (Pharma- contractions induced by 30 nM substance P for 30 s, 5 min dose-cycle; 60 min equilibration cological Data) with title comp., then relaxation induced by 1E-10 - 1E-5 5-carboxamidotryptamine (5-CT); pKB = -log(title comp. conc. M)/(conc. ratio-1) Results

concentration-dependent inhibition of 5-CT effect, pKB: 8.1

Carter; Champney; Hwang; Eglen; European Journal of Pharmacology; vol. 280; nb. 3; (1995); p. 243 - 250, View in Reaxys 69 of 79

Effect (Pharmacological Data)

neuroregulatoric

Species or Test-System (Pharmacological Data)

Sprague Dawley rat dorsal raphe 5-HT neurons

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

2 - 10 μg/kg

Method (Pharmacological Data)

weighting 200-250 g; implated with an osmotic minipump; neurons preparation; pretreatment with or without 20 mg/kg/d s.c. x 14 d; injected in a lateral vein of the tail; dose-response curve

Further Details (Pharma- 5-HT=5-hydroxytryptamine; firing activity cological Data) Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

6.1 μg/kg

Results

dose-dependently reduced the spontaneous firing activity; no effect of prolonged tianeptine administration

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Pineyro; Deveault; De Montigny; Blier; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 351; nb. 2; (1995); p. 119 - 125, View in Reaxys 70 of 79

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

rat

Method (Pharmacological Data)

in vivo; two-lever drug discrimination test in rats trained to discriminate LSD from saline; 4 6 dose levels; 8 - 12 rats tested at each dose

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.04 μmol/kg

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.; Medicinal Chemistry Research; vol. 5; nb. 9; (1995); p. 651 - 663, View in Reaxys 71 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

rat frontal cortex homogenate

Exposure Period (Pharmacological Data)

15 min

Method (Pharmacological Data)

radioligand binding; by competition with 0.75 nM <3H>ketanserin; 37 deg C; specific binding defined with 10 μM cinanserin; liquid scintillation analysis

Further Details (Pharma- affinity for serotonin 5-HT2A receptors cological Data) Type (Pharmacological Data)

Value of Type (Pharmacological Data)

4.4 nmol/l

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.; Medicinal Chemistry Research; vol. 5; nb. 9; (1995); p. 651 - 663, View in Reaxys 72 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

rat hippocampal homogenate

Exposure Period (Pharmacological Data)

10 min

Method (Pharmacological Data)

radioligand binding; by competition with 0.75 nM <3H>8-OH-DPAT; 37 deg C; specific binding determined with 10 μM 5-HT; liquid scintillation analysis

Further Details (Pharma- affinity for serotonin 5-HT1A receptors cological Data) Type (Pharmacological Data)

Value of Type (Pharmacological Data)

5.1 nmol/l

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.; Medicinal Chemistry Research; vol. 5; nb. 9; (1995); p. 651 - 663, View in Reaxys 73 of 79

Effect (Pharmacological Data)

AUC

Species or Test-System (Pharmacological Data)

dark-agouti rat

Sex

male

Route of Application

intraperitoneal

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Concentration (Pharmacological Data)

0.5 mg/kg

Kind of Dosing (Pharma- drug administered once a day for 10 successive days cological Data) Exposure Period (Pharmacological Data)

10 d

Method (Pharmacological Data)

rats 5 weeks old; back hair shaved before experiment; blood samples collected 5, 15, 30, 60, 120, 360 min after drug administration; newly grown hair samples collected 4 weeks after first drug administration

Further Details (Pharma- drug level in plasma and hair determination; GC/MS; HPLC cological Data) Type (Pharmacological Data)

AUC

Value of Type (Pharmacological Data)

10.9 μg*min/ml

Results

concentration in hair <H> = 4.4 ng/mg; drug incorporation rate ICR (<H>/AUC) = 0.4

Nakahara; Takahashi; Kikura; Biological and Pharmaceutical Bulletin; vol. 18; nb. 9; (1995); p. 1223 - 1227, View in Reaxys 74 of 79

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat brain

Sex

male

Concentration (Pharmacological Data)

0.5 nmol/l

Method (Pharmacological Data)

in vitro; animals (250-300 g) injected s.c. with either 0.5 mg/kg quipazine, 1 mg/kg ketanserin, 0.0125 mg/kg MDL 100,907; 30 min later brain removed; brain sections incubated with 125Ilabeled title comp.; autoradiography performed

Results

title comp. bound mainly to the choroid plexus; pretreatments had no effect

Smith; Barrett; Sanders-Bush; Journal of Pharmacology and Experimental Therapeutics; vol. 275; nb. 2; (1995); p. 1050 - 1057, View in Reaxys 75 of 79

Comment (Pharmacological Data)

discriminative stimulus properties in rat trained to discriminate saline treatment from ip injection of LSD tartate (two-level drug discrimination assay), ED50=0.046 μM/kg

Hoffman; Nichols; Journal of Medicinal Chemistry; vol. 28; nb. 9; (1985); p. 1252 - 1255, View in Reaxys 76 of 79

Comment (Pharmacological Data)

5-HT activity in the biochemical test 5-HT-like behavioral syndrome in the rat

Arvidsson; Hacksell; Johansson; Nilsson; Lindberg; Sanchez; Wikstroem; Svensson; Hjorth; Carlsson; Journal of Medicinal Chemistry; vol. 27; nb. 1; (1984); p. 45 - 51, View in Reaxys 77 of 79

Comment (Pharmacological Data)

effect on body temperature (150 μg/kg, i.p., rabbits) (Δt = 2.56 deg C after 60 min)

Maj; Vetulani; Michaluk; Rogoz; Skuza; Arzneimittel-Forschung/Drug Research; vol. 33; nb. 6; (1983); p. 841 - 846, View in Reaxys 78 of 79

Comment (Pharmacological Data)

effect on dose-dependent contractile responses in the middle cerebral artery of the goat induced by 5-hydroxytryptamine

Marin; Salaices; Gomez; Lluch; Journal of Pharmacy and Pharmacology; vol. 33; nb. 11; (1981); p. 715 - 719, View in Reaxys 79 of 79

Comment (Pharmacological Data)

increases the cyclic GMP content in human blood platelets

Laubscher; Pletscher; Journal of Pharmacy and Pharmacology; vol. 32; nb. 8; (1980); p. 601 - 602, View in Reaxys Concentration in the Environment (8) 1 of 8

Media (Concentration in the Environment)

sewage water

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Location

Barcelona, Spain

Contamination Concentration

2.8 ng/l

Method, Remarks (Con- samples collected from major STP of Barcelona; influent 24-h composite samples collected centration in the Environ- every day during first week of July 2007; solid-phase extraction-liquid chromatography-elecment) trospray-tandem mass spectrometry Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 3134, View in Reaxys 2 of 8

Media (Concentration in the Environment)

sewage water

Location

Barcelona, Spain

Contamination Concentration

0.3 ng/l

Method, Remarks (Con- samples collected from major STP of Barcelona; effluent 24-h composite samples collected centration in the Environ- every day during first week of July 2007; solid-phase extraction-liquid chromatography-elecment) trospray-tandem mass spectrometry Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 3134, View in Reaxys 3 of 8

Media (Concentration in the Environment)

sewage water

Location

Valencia, Spain

Contamination Concentration

1.6 ng/l

Method, Remarks (Con- samples collected from STP of tourist cites of Valencia; effluent 24-h composite samples centration in the Environ- collected on 26th of July 2007; solid-phase extraction-liquid chromatography-electrosprayment) tandem mass spectrometry Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 3134, View in Reaxys 4 of 8

Media (Concentration in the Environment)

sewage water

Location

Gandia, Spain

Contamination Concentration

1.1 ng/l

Method, Remarks (Con- samples collected from STP of tourist cites of Gandia; influent 24-h composite samples colcentration in the Environ- lected on 26th of July 2007; solid-phase extraction-liquid chromatography-electrospray-tanment) dem mass spectrometry Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 3134, View in Reaxys 5 of 8

Media (Concentration in the Environment)

sewage water

Location

Benicassim, Spain

Contamination Concentration

3.0 ng/l

Method, Remarks (Con- samples collected from STP of tourist cites of Benicassim; influent 24-h composite samples centration in the Environ- collected on 26th of July 2007; solid-phase extraction-liquid chromatography-electrosprayment) tandem mass spectrometry Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 3134, View in Reaxys 6 of 8

Media (Concentration in the Environment)

sewage water

Location

Benicassim, Spain

Contamination Concentration

0.6 ng/l

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Method, Remarks (Con- samples collected from STP of tourist cites of Benicassim; effluent 24-h composite samples centration in the Environ- collected on 26th of July 2007; solid-phase extraction-liquid chromatography-electrosprayment) tandem mass spectrometry Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 3134, View in Reaxys 7 of 8

Media (Concentration in the Environment)

sewage water

Location

Valencia, Spain

Contamination Concentration

4.7 ng/l

Method, Remarks (Con- samples collected from STP of tourist cites of Valencia; influent 24-h composite samples centration in the Environ- collected on 26th of July 2007; solid-phase extraction-liquid chromatography-electrosprayment) tandem mass spectrometry Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 3134, View in Reaxys 8 of 8

Media (Concentration in the Environment)

sewage water

Location

Gandia, Spain

Contamination Concentration

0.2 ng/l

Method, Remarks (Con- samples collected from STP of tourist cites of Gandia; effluent 24-h composite samples centration in the Environ- collected on 26th of July 2007; solid-phase extraction-liquid chromatography-electrosprayment) tandem mass spectrometry Postigo, Cristina; Lopez De Alda, Maria J.; Barcelo, Damia; Analytical Chemistry; vol. 80; nb. 9; (2008); p. 3123 3134, View in Reaxys Use (11) Use Pattern

Location

References

Parkinson's disease (PD)

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

Pharmaceuticals

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

inducing or facilitating micturition in combination with 5-HT1A receptor agonist, 5HT1A/7 receptor agonist, cholinesterase inhibitor, NMDA receptor agonist, noradrenaline/dopamine precursor

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

multiple sclerosis (MS)

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

spinal cord injury (SCI)

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

urinary retention

Page/Page column 20-23

Patent; UNIVERSITÉ LAVAL; GUERTIN, Pierre; WO2015/127558; (2015); (A1) English, View in Reaxys

hallucinogen

Patent; Renshaw, Perry F.; Cohen, Bruce M.; US2006/39890; (2006); (A1) English, View in Reaxys

interact with the GABA chloride channel complex

Patent; ABBOTT GMBH and CO.KG; WO2006/40177; (2006); (A1) English, View in Reaxys

sedative

Patent; ABBOTT GMBH and CO.KG; WO2006/40177; (2006); (A1) English, View in Reaxys

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hypnotic

Patent; ABBOTT GMBH and CO.KG; WO2006/40177; (2006); (A1) English, View in Reaxys

tranquilizer

Patent; ABBOTT GMBH and CO.KG; WO2006/40177; (2006); (A1) English, View in Reaxys

Reaxys ID 4121105 View in Reaxys

2/14 CAS Registry Number: 113-41-7; 15232-63-0; 17676-08-3; 23511-96-8; 32426-57-6; 35606-16-7; 91829-38-8 Chemical Name: LSD tartrate; (+)-lysergic acid diethylamide (+)tartrate; lysergic acid diethylamide bitartrate; D-Lysergic acid diethylamide tartrate; N,N-Diethyl-D-lysergamid-tartrat Linear Structure Formula: C20H25N3O*C4H6O6 Molecular Formula: C4H6O6*C20H25N3O Molecular Weight: 473.526 Type of Substance: heterocyclic InChI Key: HQMPRARIZOUKRO-KEZWHQCISA-N Note:

O O N

OH OH

Substance Label (1) Label References d-LSD

Odagaki; Fuxe; Journal of Pharmacology and Experimental Therapeutics; vol. 274; nb. 1; (1995); p. 337 - 344, View in Reaxys

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

Patent; Wurtman, Richard J.; Lee, Robert K. K.; US2002/173511; (2002); (A1) English, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

193 - 197

Patent; Soc. Farm. Italia; FR1338023; (1961); Chem.Abstr.; vol. 60; nb. 3026f; (1964), View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patent; Soc. Farm. Italia; FR1338023; (1961); Chem.Abstr.; vol. 60; nb. 3026f; (1964), View in Reaxys Pharmacological Data (6) 1 of 6

Comment (Pharmacological Data)

Bioactivities present

Patent; Soc. Farm. Italia; FR1338023; (1961); Chem.Abstr.; vol. 60; nb. 3026f; (1964), View in Reaxys; Oberlender, Robert; Pfaff, Robert C.; Johnson, Michael P.; Huang, Xuemei; Nichols, David E.; Journal of Medicinal Chemistry; vol. 35; nb. 2; (1992); p. 203 - 211, View in Reaxys; Oberlender; Ramachandran; Johnson; Huang; Nichols; Journal of Medicinal Chemistry; vol. 38; nb. 18; (1995); p. 3593 - 3601, View in Reaxys; Parker, Matthew A.; Marona-Lewicka, Danuta; Kurrasch, Deborah; Shulgin, Alexander T.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 41; nb. 6; (1998); p. 1001 - 1005, View in Reaxys; Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 42; nb. 20; (1999); p. 4257 - 4263, View in Reaxys; Odagaki; Fuxe; Journal of Pharmacology and Experimental Therapeutics; vol. 274; nb. 1; (1995); p. 337 - 344, View in Reaxys; Patent; Wurtman, Richard J.; Lee, Robert K. K.; US2002/173511; (2002); (A1) English, View in Reaxys; Hashimoto; Hayashi; Nakahara; Niwaguchi; Ishii; European Journal of Pharmacology; vol. 45; nb. 4; (1977); p. 341 - 348, View in Reaxys; Teitler, Milt; Scheick, Cynthia; Howard, Paul; Sullivan III, Joseph E.; Iwamura, Tatsunori; Glennon, Richard A.; Medicinal Chemistry Research; vol. 7; nb. 4; (1997); p. 207 - 218, View in Reaxys; Parker; Marona-Lewicka; Kurrasch; Shulgin; Nichols; Journal of Medicinal Chemistry; vol. 41; nb. 6; (1998); p. 1001 - 1005, View in Reaxys; To; Bonhaus; Eglen; Jakeman; British Journal of Pharmacology; vol. 115; nb. 1; (1995); p. 107 - 116, View in Reaxys; Oberlender; Pfaff; Johnson; Huang; Nichols; Journal of Medicinal Chemistry; vol. 35; nb. 2; (1992); p. 203 - 211, View in Reaxys; Markstein; Hoyer; Engel; Naunyn-

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Schmiedeberg's archives of pharmacology; vol. 333; nb. 4; (1986); p. 335 - 341, View in Reaxys; De Vivo; Maayani; The Journal of pharmacology and experimental therapeutics; vol. 238; nb. 1; (1986); p. 248 - 253, View in Reaxys; Nichols; Jadhav; Oberlender; Zabik; Bossart; Hamada; Miller; Journal of Medicinal Chemistry; vol. 27; nb. 9; (1984); p. 1108 - 1111, View in Reaxys; Spencer, P S; British journal of pharmacology and chemotherapy; vol. 25; nb. 2; (1965); p. 442 - 55, View in Reaxys; ; (2012); Type: Review, Lab: EFF_071212, Owner: EFFECT, Number: 000, Revision: 07.12.2012 00:00:00, View in Reaxys; Eshleman, Amy J.; Forster, Michael J.; Wolfrum, Katherine M.; Johnson, Robert A.; Janowsky, Aaron; Gatch, Michael B.; Psychopharmacology; vol. 231; nb. 5; (2014); p. 875 888, View in Reaxys 2 of 6

Comment (Pharmacological Data)

physiological behaviour discussed

Eshleman, Amy J.; Forster, Michael J.; Wolfrum, Katherine M.; Johnson, Robert A.; Janowsky, Aaron; Gatch, Michael B.; Psychopharmacology; vol. 231; nb. 5; (2014); p. 875 - 888, View in Reaxys 3 of 6

Comment (Pharmacological Data)

in vivo (male Sprague-Dawley rats) ability to discriminate serotonin-releasing agents and hallucinogens from saline: ED50=0.04 μmol/kg

Parker, Matthew A.; Marona-Lewicka, Danuta; Kurrasch, Deborah; Shulgin, Alexander T.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 41; nb. 6; (1998); p. 1001 - 1005, View in Reaxys 4 of 6

in vivo hallucinogenic effect in LSD-trained rats ED50=0.02 μmol/kg (ip); in vitro binding at 5-HT2 serotonin receptor in rat frontal cortex

Comment (Pharmacological Data)

Oberlender; Ramachandran; Johnson; Huang; Nichols; Journal of Medicinal Chemistry; vol. 38; nb. 18; (1995); p. 3593 - 3601, View in Reaxys 5 of 6

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat hippocampal membrane

Sex

male

Method (Pharmacological Data)

rat weight 200 - 250 g; decapitation; hippocampal membrane isolation; title comp. 15 min incubation at 30 deg C with 0.3 μmol/l <γ-32P>GTP and 2 mmol/l MgCl2; <32P>phosphate determined by liquid scintillation

Further Details (Pharma- GTP hydrolysis by high-affinity GTPase in 5-HT1A receptor-coupled G protein cological Data) Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

11 nmol/l

Results

agonist; correlation with inhibition of forskolin-stimulated adenylyl cyclase activity in guinea pig or rat hippocampal membranes (diagram)

Odagaki; Fuxe; Journal of Pharmacology and Experimental Therapeutics; vol. 274; nb. 1; (1995); p. 337 - 344, View in Reaxys 6 of 6

Comment (Pharmacological Data)

in vivo drug discrimination potency in d-LSD tartrate-trained rats, ED50 27.5 nmol/kg; in vitro binding affinity for rat cortical homogenate 5-HT2 receptors; in vitro binding affinity for rat hippocampal 5-HT1A receptors

Oberlender, Robert; Pfaff, Robert C.; Johnson, Michael P.; Huang, Xuemei; Nichols, David E.; Journal of Medicinal Chemistry; vol. 35; nb. 2; (1992); p. 203 - 211, View in Reaxys

Reaxys ID 10619199 View in Reaxys

3/14 Chemical Name: LSD hydrochloride; d-lysergic acid diethylamine hydrochloride Linear Structure Formula: C20H25N3O*ClH Molecular Formula: C20H25N3O*ClH Molecular Weight: 359.899 Type of Substance: heterocyclic InChI Key: PUMCBUMWYUTCBD-KEZWHQCISA-N Note:

O N

HN H

Substance Label (1)

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Label

References

LSD

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

Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

Blair, Joseph B.; Marona-Lewicka, Danuta; Kanthasamy, Arthi; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.; Journal of Medicinal Chemistry; vol. 42; nb. 6; (1999); p. 1106 - 1111, 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; Whitaker; Seeman; Psychopharmacology; vol. 59; nb. 1; (1978); p. 1 - 5, View in Reaxys; ; (2012); Type: Review, Lab: EFF_071212, Owner: EFFECT, Number: 000, Revision: 07.12.2012 00:00:00, View in Reaxys 2 of 4

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

Value of Type (Pharmacological Data)

0.40 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 4

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

Value of Type (Pharmacological Data)

0.81 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 4 of 4

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

EC50

Value of Type (Pharmacological Data)

0.22 nmol/l

Results

intrinsic activity was 84 percent

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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

Reaxys ID 25263076 View in Reaxys

4/14 Chemical Name: [3H]LSD Linear Structure Formula: C20H22 (3)H3N3O Molecular Formula: C20H25N3O Molecular Weight: 329.414 InChI Key: VAYOSLLFUXYJDT-QZGBZKRISA-N Note:

N O HN N H 3H

3H 3H

Substance Label (1) Label References [3H]LSD

Waszkielewicz, Anna M.; Cegla, Marek; Zeslawska, Ewa; Nitek, Wojciech; Sloczyska, Karolina; Marona, Henryk; Bioorganic and Medicinal Chemistry; vol. 23; nb. 15; (2015); p. 4197 - 4217, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Rosse, Gerard; Schaffhauser, Herve; Current Topics in Medicinal Chemistry; vol. 10; nb. 2; (2010); p. 207 - 221, View in Reaxys; Waszkielewicz, Anna M.; Cegla, Marek; Zeslawska, Ewa; Nitek, Wojciech; Sloczyska, Karolina; Marona, Henryk; Bioorganic and Medicinal Chemistry; vol. 23; nb. 15; (2015); p. 4197 - 4217, View in Reaxys

Reaxys ID 4121106 View in Reaxys

5/14 CAS Registry Number: 113-41-7 Chemical Name: LSD-tartrat Linear Structure Formula: C20H25N3O*C4H6O6 Molecular Formula: C4H6O6*C20H25N3O Molecular Weight: 473.526 Type of Substance: heterocyclic InChI Key: HQMPRARIZOUKRO-AJLBZGGQSA-N Note:

O OH O H HN

N H

H OH O

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Bowd et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1973); p. 1312, View in Reaxys Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Fluorescence

Bowd et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1973); p. 1312, View in Reaxys

Phosphorescence Spectroscopy (1) Description References (Phosphorescence Spectroscopy) Phosphorescence Bowd et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1973); p. 1312, View in Reaxys

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Reaxys ID 6841306 View in Reaxys

6/14 Linear Structure Formula: C21H18O5S*C20H25N3O Molecular Formula: C20H25N3O*C21H18O5S Molecular Weight: 705.875 Type of Substance: heterocyclic InChI Key: ZSSHFTXVEIGWNH-SNAJOTIRSA-N Note:

O O

HN N H

Substance Label (1) Label References V*LSD

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

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

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Solvent (Liquid/Liquid Systems (MCS))

H2O

Partner (Liquid/Liquid Systems (MCS))

chloroform; buffer, pH 2.5

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

CHCl3

Comment (UV/VIS Spectroscopy)

320 - 720 nm

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

CHCl3

Absorption Maxima (UV/ 406 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

26300

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

Reaxys ID 6841550 View in Reaxys

7/14 O

Linear Structure Formula: C23H22O5S*C20H25N3O Molecular Formula: C20H25N3O*C23H22O5S Molecular Weight: 733.929 Type of Substance: heterocyclic InChI Key: UMKUQMPTCYOYEZ-SNAJOTIRSA-N Note:

O S

O N

N H HO

Substance Label (1) Label References

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III*LSD

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

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

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Solvent (Liquid/Liquid Systems (MCS))

H2O

Partner (Liquid/Liquid Systems (MCS))

chloroform; buffer, pH 2.7

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

CHCl3

Comment (UV/VIS Spectroscopy)

320 - 720 nm

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

CHCl3

Absorption Maxima (UV/ 370 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

15500

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

Reaxys ID 6841663 View in Reaxys

8/14 Linear Structure Formula: C23H20Br2O5S*C20H25N3O Molecular Formula: C20H25N3O*C23H20Br2O5S Molecular Weight: 891.721 Type of Substance: heterocyclic InChI Key: BZZJEKAMVVEFHW-DIPMGBITSA-N Note:

O E

Br N

HN N H

Br HO

Substance Label (1) Label References LSD*II, A

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

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

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Solvent (Liquid/Liquid Systems (MCS))

H2O

Partner (Liquid/Liquid Systems (MCS))

chloroform; buffer, pH 3.0

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Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

CHCl3

Comment (UV/VIS Spectroscopy)

320 - 720 nm

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

CHCl3

Absorption Maxima (UV/ 412 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

23800

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

Reaxys ID 6841961 View in Reaxys

9/14 Linear Structure Formula: C20H25N3O*C16H11N2O4S(1-)*Na(1+) Molecular Formula: C16H11N2O4S*C20H25N3O*Na Molecular Weight: 673.768 Type of Substance: heterocyclic InChI Key: GXDFYJKGPOSPHA-ROIBWGDASA-M Note:

N N

O–

O N

Na +

N H

Substance Label (1) Label References VI*LSD

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

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

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Solvent (Liquid/Liquid Systems (MCS))

H2O

Partner (Liquid/Liquid Systems (MCS))

chloroform; buffer, pH 2.0

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Spectrum

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Solvent (UV/VIS Spectroscopy)

CHCl3

Comment (UV/VIS Spectroscopy)

320 - 720 nm

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

CHCl3

Absorption Maxima (UV/ 495 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

18300

Skalican, Zdenek; Kobliha, Zbynek; Halamek, Emil; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 3; (1994); p. 575 - 581, View in Reaxys

Reaxys ID 9082736 View in Reaxys

10/14 Linear Structure Formula: C20H24TN3O Molecular Formula: C20H25N3O Molecular Weight: 325.43 Type of Substance: heterocyclic InChI Key: VAYOSLLFUXYJDT-NQYDAWTJSA-N Note:

O N

HN H

Substance Label (1) Label References (2-3H)-LSD

Nagasaki, Tohru; Sakai, Katsunori; Segawa, Masaharu; Katsuyama, Yoshihiko; Haga, Nobuhiro; Koike, Masahiro; Kawada, Kenji; Takechi, Shozo; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 44; nb. 14; (2001); p. 993 - 1004, View in Reaxys

Reaxys ID 15797861 View in Reaxys

11/14

Chemical Name: (+)-d-lysergic acid diethylamide (+)-tartrate Linear Structure Formula: C4H6O6*2C20H25N3O Molecular Formula: C4H6O6*2C20H25N3O Molecular Weight: 796.964 InChI Key: HQMPRARIZOUKRO-AJLBZGGQSA-N Note:

2 HN

O N

OH O

Substance Label (1) Label References d-LSD

Reissig, Chad J.; Rabin, Richard A.; Winter, Jerrold C.; Dlugos, Cynthia A.; European Journal of Pharmacology; vol. 583; nb. 1; (2008); p. 40 - 47, View in Reaxys

Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Reissig, Chad J.; Rabin, Richard A.; Winter, Jerrold C.; Dlugos, Cynthia A.; European Journal of Pharmacology; vol. 583; nb. 1; (2008); p. 40 - 47, View in Reaxys 2 of 3

Effect (Pharmacological Data)

protein expression; induction of

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Species or Test-System (Pharmacological Data)

Fischer 344 rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.1 - 1 mg/kg

Kind of Dosing (Pharma- dissolved in saline cological Data) Method (Pharmacological Data)

title comp. administered; after 90 min rats perfused with saline; forebrains fixed, sectioned; expression of c-Fos protein analysed by immunocytochemistry

Further Details (Pharma- control: saline cological Data) Results

title comp. dose-depend. induced expression of c-Fos protein in nuclei of prefrontal cortex

Reissig, Chad J.; Rabin, Richard A.; Winter, Jerrold C.; Dlugos, Cynthia A.; European Journal of Pharmacology; vol. 583; nb. 1; (2008); p. 40 - 47, View in Reaxys 3 of 3

Effect (Pharmacological Data)

protein expression; induction of

Species or Test-System (Pharmacological Data)

Fischer 344 rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.1 - 1 mg/kg

Kind of Dosing (Pharma- dissolved in saline cological Data) Method (Pharmacological Data)

title comp. administered; after 90 min forebrains sectioned; neurons, astrocytes, oligodendrocytes and microglia labeled with specific cell markers; c-Fos labeled with antibody; colocalization of c-Fos with cell markers performed microscopically

Further Details (Pharma- control: saline cological Data) Results

title comp. induced expression of c-Fos protein in subpopulations of NeuN-labeled neurons and in oligodendrocytes, but not in pyramidal neurons, astrocytes and microglia

Reissig, Chad J.; Rabin, Richard A.; Winter, Jerrold C.; Dlugos, Cynthia A.; European Journal of Pharmacology; vol. 583; nb. 1; (2008); p. 40 - 47, View in Reaxys

Reaxys ID 25337035 View in Reaxys

Linear Structure Formula: C4H4O4*C20H25N3O Molecular Formula: C4H4O4*C20H25N3O Molecular Weight: 439.511 InChI Key: PBZHMSZIBQNTPH-ZYXUSYCASA-N Note:

Z O

12/14

OH OH O

N H

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Johnson; Ary; Teiger; Kassel; Journal of medicinal chemistry; vol. 16; nb. 5; (1973); p. 532 - 537, View in Reaxys

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Reaxys ID 25679261 View in Reaxys

13/14 Linear Structure Formula: C20H25N3O*H(1+) Molecular Formula: C20H25N3O*H Molecular Weight: 324.446 InChI Key: VAYOSLLFUXYJDT-RDTXWAMCSA-O Note:

N H+

HN N

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Vermeulen, Erik S.; Schmidt, Anne W.; Sprouse, Jeffrey S.; Wikstroem, Hakan V.; Grol, Cor J.; Journal of Medicinal Chemistry; vol. 46; nb. 25; (2003); p. 5365 - 5374, View in Reaxys

Reaxys ID 28058985 View in Reaxys

14/14 (3)HN

Linear Structure Formula: C20H24 3O Molecular Formula: C20H25N3O Molecular Weight: 325.43 InChI Key: VAYOSLLFUXYJDT-ZYMNUHEPSA-N Note:

N O H N

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