Reaxys
PubChem
Reactions (4)
Substances (1)
Citations (34)
Structure
N° of preparations All Preps | All Reactions
Structure/Compound Data Chemical Name: 2-bromo-lysergide Reaxys Registry Number: 46871
CAS Registry Number: 478-84-2 Type of Substance: heterocyclic Molecular Formula: C20H24BrN3O Linear Structure Formula: C20H24BrN3O Molecular Weight: 402.334 InChI Key: VKRAXSZEDRWLAG-SJKOYZFVSA-N
1
2 prep out of 4 reactions.
Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-bromo-lysergide, Bromolysergide, 2-bromo-5R,8R-lysergic acid diethyl amide, 2-bromo-6-methyl-9,10-didehydro-ergoline-8-carboxylic acid diethylamide, (5R,8R)2-bromo-lysergic acid diethyl amide Identification Substance Label (1) Label
Reference
2; R&1%=H,R&2%=Br,R...
Stanovnik, Branko; Tisler, Miha; Jurgec, Milan; Rucman, Rudolf
Heterocycles, 1981 , vol. 16, # 5 p. 741 - 745 Title/Abstract Full Text Show Details
Derivative (1) Comment (Derivative)
Reference
Available Data
N° of ref.
Identification Physical Data (5) Spectra (5) Bioactivity (4)
34
Troxler; Hofmann
Helvetica Chimica Acta, 1957 , vol. 40, p. 2160,2169 Full Text Show Details
Lg-hydrogentartrate (mp: 130-140 degree ; <alpha>=34 degree ) Further Data see Handbook
Physical Data Melting Point (1) Melting Point
Solvent (Melting Point)
Reference
120 - 127 °C
diethyl ether
Troxler; Hofmann
Helvetica Chimica Acta, 1957 , vol. 40, p. 2160,2169 Full Text Show Details
Optical Rotatory Power (4) Type (Optical Rotatory Power)
Concentration (Optical Rotatory Power)
Solvent (Optical Rotatory Power)
Optical Rotatory Power
Wavelength (Optical Rotatory Power)
Temperature (Optical Rotatory Power)
Reference Sandoz Ltd.
Patent: US4609731 A1, 1986 ; Title/Abstract Full Text Show Details
[alpha]
1 g/100ml
pyridine
17 deg
589 nm
20 °C
Stanovnik, Branko; Tisler, Miha; Jurgec, Milan; Rucman, Rudolf
Heterocycles, 1981 , vol. 16, # 5 p. 741 - 745 Title/Abstract Full Text Show Details
[alpha]
c=0.5
CHCl3
53 deg
589 nm
20 °C
Troxler; Hofmann
Helvetica Chimica Acta, 1957 , vol. 40, p. 2160,2169 Full Text Show Details
[alpha]
c=0.5
pyridine
15 deg
589 nm
20 °C
Troxler; Hofmann
Helvetica Chimica Acta, 1957 , vol. 40, p. 2160,2169 Full Text Show Details
Spectra IR Spectroscopy (1) Description (IR Spectroscopy)
Solvent (IR Spectroscopy)
Comment (IR Spectroscopy)
Reference
Spectrum
nujol
3500 - 650 cm**(-1)
Troxler; Hofmann
Helvetica Chimica Acta, 1957 , vol. 40, p. 2160,2169 Full Text Show Details
UV/VIS Spectroscopy (2) Description (UV/VIS Spectroscopy)
Solvent (UV/VIS Spectroscopy)
Comment (UV/VIS Spectroscopy)
Bowd et al.
Journal of the Chemical Society [Section] B: Physical Organic, 1971 , p. 1509 Full Text View citing articles Show Details
Absorption maxima
Spectrum
Reference
ethanol
210 - 350 nm
Troxler; Hofmann
Helvetica Chimica Acta, 1957 , vol. 40, p. 2160,2169 Full Text Show Details
Fluorescence Spectroscopy (1) Description (Fluorescence Spectroscopy)
Solvent (Fluorescence Spectroscopy)
Comment (Fluorescence Spectroscopy)
Reference
Maxima
H2O
460 nm in Loesung vom pH 1.
Udenfriend et al.
Journal of Pharmacology and Experimental Therapeutics, 1957 ,
vol. 120, p. 26,29 Full Text Show Details
Phosphorescence Spectroscopy (1) Description (Phosphorescence Spectroscopy)
Reference
Phosphorescence
Bowd et al.
Journal of the Chemical Society [Section] B: Physical Organic, 1971 , p. 1509 Full Text View citing articles Show Details
Bioactivity Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Reference
Sibley, David R.; Monsma JR., Frederick J.; Hamblin, Mark
Patent: US2002/91235 A1, 2002 ; Title/Abstract Full Text Show Details
Troxler; Hofmann
Helvetica Chimica Acta, 1957 , vol. 40, p. 2160,2169 Full Text Show Details
Udenfriend et al.
Journal of Pharmacology and Experimental Therapeutics, 1957 , vol. 120, p. 26,29 Full Text Show Details
Bowd et al.
Journal of the Chemical Society [Section] B: Physical Organic, 1971 , p. 1509 Full Text View citing articles Show Details
Stanovnik, Branko; Tisler, Miha; Jurgec, Milan; Rucman, Rudolf
Heterocycles, 1981 , vol. 16, # 5 p. 741 - 745 Title/Abstract Full Text Show Details
Lopez-Rodriguez, Maria L.; Porras, Esther; Benhamu, Bellinda; Ramos, Jose. A.; Morcillo, M. Jose; Lavandera, Jose L.
Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 10 p. 1097 - 1100 Title/Abstract Full Text View citing articles Show Details
Nagasaki, Tohru; Sakai, Katsunori; Segawa, Masaharu; Katsuyama, Yoshihiko; Haga, Nobuhiro; Koike, Masahiro; Kawada, Kenji; Takechi, Shozo
Journal of Labelled Compounds and Radiopharmaceuticals, 2001 , vol. 44, # 14 p. 993 - 1004 Title/Abstract Full Text Show Details
Ebersole, Barbara J.; Visiers, Irache; Weinstein, Harel; Sealfon, Stuart C.
Molecular Pharmacology, 2003 , vol. 63, # 1 p. 36 - 43 Title/Abstract Full Text View citing articles Show Details
Glennon, Richard A.
Journal of Medicinal Chemistry, 2003 , vol. 46, # 14 p. 2795 - 2812 Title/Abstract Full Text View citing articles Show Details
Lopez-Rodriguez, Maria L.; Porras, Esther; Morcillo, M. Jose; Benhamu, Bellinda; Soto, Luis J.; Lavandera, Jose L.; Ramos, Jose A.; Olivella, Mireia; Campillo, Mercedes; Pardo, Leonardo
Journal of Medicinal Chemistry, 2003 , vol. 46, # 26 p. 5638 - 5650 Title/Abstract Full Text View citing articles Show Details
Berg, Kelly A.; Stout, Brian D.; Cropper, Jodie D.; Maayani, Saul; Clarke, William P.
Molecular Pharmacology, 1999 , vol. 55, # 5 p. 863 - 872 Title/Abstract Full Text View citing articles Show Details
Guang, Wei; Wang, Hongyan; Su, Tao; Weinstein, I. Bernard; Jia, Bei Wang
Molecular Pharmacology, 2004 , vol. 66, # 5 p. 1285 - 1292 Title/Abstract Full Text View citing articles Show Details
Kolaczkowski, Marcin; Nowak, Mateusz; Pawlowski, Maciej; Bojarski, Andrzej J.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 23 p. 6732 - 6741 Title/Abstract Full Text View citing articles Show Details
Sandoz Ltd.
Patent: US4609731 A1, 1986 ; Title/Abstract Full Text Show Details
Burt; Creese; Snyder
Molecular pharmacology, 1976 , vol. 12, # 5 p. 800 - 812 Title/Abstract Full Text Show Details
Bennett Jr; Snyder
Molecular Pharmacology, 1976 , vol. 12, # 3 p. 373 - 389 Title/Abstract Full Text View citing articles Show Details
Lovell; Freedman
Molecular Pharmacology, 1976 , vol. 12, # 4 p. 620 - 630 Title/Abstract Full Text View citing articles Show Details
Green; Johnson; Weinstein; Maayani
Proceedings of the National Academy of Sciences of the United States of America, 1977 , vol. 74, # 12 p. 5697 - 5701 Title/Abstract Full Text View citing articles Show Details
Leopoldo
Current Medicinal Chemistry, 2004 , vol. 11, # 5 p. 629 - 661 Title/Abstract Full Text View citing articles Show Details
Bard; Zgombick; Adham; Vaysse; Branchek; Weinshank
Journal of Biological Chemistry, 1993 , vol. 268, # 31 p. 23422 - 23426
Title/Abstract Full Text Show Details
2 of 4
Comment (Pharmacological Data)
Bioactivities present
Reference
Monsma Jr.; Shen; Ward; Hamblin; Sibley
Molecular Pharmacology, 1993 , vol. 43, # 3 p. 320 - 327 Title/Abstract Full Text Show Details
Wainscott; Cohen; Schenck; Audia; Nissen; Baez; Kursar; Lucaites; Nelson
Molecular Pharmacology, 1993 , vol. 43, # 3 p. 419 - 426 Title/Abstract Full Text Show Details
Perry
The Journal of pharmacology and experimental therapeutics, 1986 , vol. 236, # 2 p. 548 - 559 Title/Abstract Full Text Show Details
Weiss; Drummond
Molecular Pharmacology, 1981 , vol. 20, # 3 p. 592 - 597 Title/Abstract Full Text View citing articles Show Details
Peroutka; Snyder
Molecular Pharmacology, 1979 , vol. 16, # 3 p. 687 - 699 Title/Abstract Full Text View citing articles Show Details
Northup; Mansour
Molecular Pharmacology, 1978 , vol. 14, # 5 p. 804 - 819 Title/Abstract Full Text View citing articles Show Details
Bard, Jonathan A.; Branchek, Theresa; Weinshank, Richard L.
Patent: US2003/166066 A1, 2003 ; Title/Abstract Full Text Show Details
Sibley, David R.; Monsma, Frederick J.; Hamblin, Mark
Patent: US2002/91235 A1, 2002 ; Title/Abstract Full Text Show Details
vol. AD27768 Full Text Show Details
HARRIS ISBELL; E. J. MINER; C. R. L0GAN
Psychopharmacology, 1959 , vol. 1, p. 20 - 28 Full Text Show Details
LASZLO GYERMEK
Journal of medicinal chemistry, 1964 , vol. 7, # 3 p. 280 - 284 Title/Abstract Full Text View citing articles Show Details
Full Text Show Details
ROTHLIN E.
Annals of the New York Academy of Sciences, 1957 , vol. 66, # 3 p. 668 - 676 Full Text Show Details
M.L. Lopez-Rodriguez; B. Benhamu; M.J. Morcillo; E. Porras; J.L. Lavandera; L. Pardo Current Medicinal Chemistry: Central Nervous System Agents, 2004 , vol. 4, # 3 p. 203 - 214 Title/Abstract Full Text Show Details
3 of 4
4 of 4
Effect (Pharmacological Data)
receptor systems; effect on
Species or TestSystem (Pharmacological Data)
CHO-1C19 cells expressing human 5-HT2C receptors
Concentration (Pharmacological Data)
700 nmol/l
Method (Pharmacological Data)
cells labeled with <3H>AA (4 h) and <3H>-myo-inositol (24 h); labeled cells incubated with title comp. for 24 h; IP accumulation in response to 1 μmol/l DOI (10 min, 37 deg C) determined
Further Details (Pharmacological Data)
CHO-1C19: Chinese hamster ovary K1 cells "low" expressing human 5-HT2C receptors (about 250 fmol/mg); DOI: (+/-)-1-(2,5-dimethoxy4-iodophenyl)-2-aminopropane, 5-HT2C (serotonin) agonist; AA: arachidonic acid; IP: inositol phosphate; vehicle control
Results
title comp. increased DOI-mediated IP accumulation acting as inverse agonist (diagram)
Reference
Berg, Kelly A.; Stout, Brian D.; Cropper, Jodie D.; Maayani, Saul; Clarke, William P.
Molecular Pharmacology, 1999 , vol. 55, # 5 p. 863 - 872 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
receptor systems; effect on
Species or TestSystem (Pharmacological Data)
CHO-1C7 cells expressing human 5-HT2C receptors
Concentration
700 nmol/l
(Pharmacological Data) Method (Pharmacological Data)
cells labeled with <3H>AA (4 h) and <3H>-myo-inositol (24 h); labeled cells incubated in medium with title comp. at 37 deg C for 25 min in the presence of 20 mmol/l LiCl and 0.1 percent BSA; AA release and IP accumulation determined
Further Details (Pharmacological Data)
CHO-1C7: Chinese hamster ovary K1 cells "high" expressing human 5-HT2C receptors (about 5-10 pmol/mg); 5-HT: serotonin; AA: arachidonic acid; IP: inositol phosphate; vehicle control
Comment (Pharmacological Data)
No effect
Reference
Berg, Kelly A.; Stout, Brian D.; Cropper, Jodie D.; Maayani, Saul; Clarke, William P.
Molecular Pharmacology, 1999 , vol. 55, # 5 p. 863 - 872 Title/Abstract Full Text View citing articles Show Details