2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine (2C-I) by Asch

Query Query

Results

Date

4 substances in Reaxys

2016-05-27 13h:04m:28s (EST)

O NH 2

1. Query I O

Search as: As drawn

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Reaxys ID 2723935 View in Reaxys

1/4 CAS Registry Number: 69587-11-7 Chemical Name: 2-(4-iodo-2,5-dimethoxyphenyl)ethylamine; 2(4-iodo-2.5-dimethoxyphenyl)ethylamine; 1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane; 2-(2,5-dimethoxy-4-iodophenyl)-aminoethane; 4-iodo-2,5-dimethoxyphenethylamine; 2-(4-iodo-2,5dimethoxy-phenyl)-ethylamine; 2-(2,5-Dimethoxy-4-iodphenyl)aethylamin Linear Structure Formula: C10H14INO2 Molecular Formula: C10H14INO2 Molecular Weight: 307.131 Type of Substance: isocyclic InChI Key: PQHQBRJAAZQXHL-UHFFFAOYSA-N Note:

O NH 2 I O

Substance Label (4) Label References 2

Nichols, David E.; Sassano, M. Flori; Halberstadt, Adam L.; Klein, Landon M.; Brandt, Simon D.; Elliott, Simon P.; Fiedler, Wolfgang J.; ACS Chemical Neuroscience; vol. 6; nb. 7; (2015); p. 1165 - 1175, View in Reaxys

2C-I

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo; British journal of pharmacology; vol. 136; nb. 4; (2002); p. 510 - 519, View in Reaxys; Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys; Theobald, Denis S.; Puetz, Michael; Schneider, Erhard; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 41; nb. 7; (2006); p. 872 - 886, View in Reaxys; Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; SaezBriones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.; Journal of Pharmacology and Experimental Therapeutics; vol. 321; nb. 3; (2007); p. 1054 - 1061, View in Reaxys; Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys; Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys

Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.; Journal of Medicinal Chemistry; vol. 37; nb. 25; (1994); p. 4346 - 4351, View in Reaxys; Claudi, Francesco; Scoccia, Loredana; Giorgioni, Gianfabio; Accorroni, Beatrice; Marucci, Gabriella; Gessi, Stefania; Siniscalchi, Anna; Borea, Pier Andrea; European Journal of Medicinal Chemistry; vol. 34; nb. 10; (1999); p. 843 - 852, View in Reaxys

Braun et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1543, View in Reaxys

Derivative (1) Comment (Derivative)

References

Hydrochlorid: F.: 246-247grad, 1HNMR

Braun et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1543, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties colourless

Trachsel, Daniel; Nichols, David E.; Kidd, Stephanie; Hadorn, Marcel; Baumberger, Franz; Chemistry and Biodiversity; vol. 6; nb. 5; (2009); p. 692 - 704, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI); fragmentation pattern

Theobald, Denis S.; Puetz, Michael; Schneider, Erhard; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 41; nb. 7; (2006); p. 872 - 886, View in Reaxys

Pharmacological Data (21) 1 of 21

Comment (Pharmacological Data)

Bioactivities present

Braun et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1543, View in Reaxys; Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.; Journal of Medicinal Chemistry; vol. 37; nb. 25; (1994); p. 4346 - 4351, View in Reaxys; Clare, Brian W.; Journal of Medicinal Chemistry; vol. 41; nb. 20; (1998); p. 3845 - 3856, View in Reaxys; Claudi, Francesco; Scoccia, Loredana; Giorgioni, Gianfabio; Accorroni, Beatrice; Marucci, Gabriella; Gessi, Stefania; Siniscalchi, Anna; Borea, Pier Andrea; European Journal of

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Medicinal Chemistry; vol. 34; nb. 10; (1999); p. 843 - 852, View in Reaxys; Cozzi; Nichols; European journal of pharmacology; vol. 309; nb. 1; (1996); p. 25 - 31, View in Reaxys; Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo; British journal of pharmacology; vol. 136; nb. 4; (2002); p. 510 - 519, View in Reaxys; Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys; Theobald, Denis S.; Puetz, Michael; Schneider, Erhard; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 41; nb. 7; (2006); p. 872 - 886, 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; Theobald, Denis S.; Maurer, Hans H.; Biochemical Pharmacology; vol. 73; nb. 2; (2007); p. 287 - 297, View in Reaxys; Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.; Journal of Pharmacology and Experimental Therapeutics; vol. 321; nb. 3; (2007); p. 1054 - 1061, View in Reaxys; Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys; Nonaka, Ryouichi; Nagai, Fumiko; Ogata, Akio; Satoh, Kanako; Biological and Pharmaceutical Bulletin; vol. 30; nb. 12; (2007); p. 2328 - 2333, View in Reaxys; Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys; Trachsel, Daniel; Nichols, David E.; Kidd, Stephanie; Hadorn, Marcel; Baumberger, Franz; Chemistry and Biodiversity; vol. 6; nb. 5; (2009); p. 692 - 704, View in Reaxys; Parrish, Jason C.; Braden, Michael R.; Gundy, Emily; Nichols, David E.; Journal of Neurochemistry; vol. 95; nb. 6; (2005); p. 1575 - 1584, View in Reaxys; Blaazer, Antoni R.; Smid, Pieter; Kruse, Chris G.; ChemMedChem; vol. 3; nb. 9; (2008); p. 1299 - 1309, View in Reaxys; Meyer, Markus R.; Maurer, Hans H.; Current Drug Metabolism; vol. 11; nb. 5; (2010); p. 468 - 482, View in Reaxys; Braun; Shulgin; Sargent III; Journal of Medicinal Chemistry; vol. 20; nb. 12; (1977); p. 1543 - 1546, View in Reaxys; Cozzi, Nicholas V.; Nichols, David E.; European Journal of Pharmacology; vol. 309; nb. 1; (1996); p. 25 - 31, View in Reaxys; Nichols; Frescas; Marona-Lewicka; Huang; Roth; Gudelsky; Nash; Journal of Medicinal Chemistry; vol. 37; nb. 25; (1994); p. 4346 4351, View in Reaxys; Johnson; Mathis; Shulgin; Hoffman; Nichols; Pharmacology, biochemistry, and behavior; vol. 35; nb. 1; (1990); p. 211 - 217, View in Reaxys; SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL; Chemical reviews; vol. 83; nb. 6; (1983); p. 633 - 649, View in Reaxys; Francesco Claudi; Loredana Scoccia; Gianfabio Giorgioni; Beatrice Accorroni; Gabriella Marucci; Stefania Gessi; Anna Siniscalchi; Pier Andrea Borea; European journal of medicinal chemistry; vol. 34; nb. 10; (1999); p. 843 - 852, View in Reaxys; Nichols, David E.; Sassano, M. Flori; Halberstadt, Adam L.; Klein, Landon M.; Brandt, Simon D.; Elliott, Simon P.; Fiedler, Wolfgang J.; ACS Chemical Neuroscience; vol. 6; nb. 7; (2015); p. 1165 - 1175, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 2 of 21

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 3 of 21

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

8.4 μmol/kg

Method (Pharmacological Data)

immediately after title comp. injection rats placed in dark Plexiglas box and number of head shakes was quantified for 25 min, starting 5 min after title comp. administration

Further Details (Pharmacological Data)

control: saline; 5-HT: serotonin

Comment (Pharmacological Data)

No effect

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.; Journal of Pharmacology and Experimental Therapeutics; vol. 321; nb. 3; (2007); p. 1054 - 1061, View in Reaxys 4 of 21

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

CHO-1C19 cells expressing human 5-HT2C receptors

Method (Pharmacological Data)

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

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Further Details (Pharmacological Data)

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

Results

title comp. had almost similar relative efficacies for PLC-mediated IP accumulation (RE = ca. 55percent and pEC50 = 6.27) and for PLA2-mediated AA release (RE = ca. 55percent, pEC50 = 6.46) (figures, table)

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

CHO-1C19 cells expressing human 5-HT2A receptors

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Results

title comp. preferentially stimulated PLC-mediated IP accumulation (RE = ca. 30percent, pEC50 = 6.29); RE for PLA2-mediated AA response was ca. 20percent, pEC50 = 6.55 (figures, table)

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 99.1percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>norepinephrine added to plate containing title comp.; 30 min at 25 deg C; scintillation counted

Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 1.1E-8 M); cocaine: no effect

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 1E-4 mol/l

Results

title comp. had little effect on norepinephrine release

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 7 of 21

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 99.1percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>5-HT added to plate containing title comp.; 30 min at 25 deg C; scintillation counted

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Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 7.9E-7 M); cocaine: no effect; 5-HT: serotonin

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 1E-4 mol/l

Results

title comp. had little effect on 5-HT release

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 8 of 21

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain crude striatum synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 99.1percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>dopamine added to plate containing title comp.; 5 min at 25 deg C; scintillation counted

Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 2.80E-8 M); cocaine: no effect

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 1E-4 mol/l

Results

title comp. had little effect on dopamine release

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 9 of 21

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 99.1percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>norepinephrine addition; 5 min at 37 deg C; scintillation counted

Further Details (Pharmacological Data)

non-specific uptake obtained at 0 deg C; positive control: cocaine (IC50 = 3.4E-7 M) and methamphetamine (IC50 = 2.0E-7 M)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

3.7E-5 mol/l

Results

title comp. slightly inhibited norepinephrine re-uptake

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 10 of 21

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain crude striatum synaptosomes of Sprague-Dawley rat

Sex

male

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Kind of Dosing (Pharmacological Data)

title comp. purity was 99.1percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>dopamine addition; 5 min at 37 deg C; scintillation counted

Further Details (Pharmacological Data)

non-specific uptake obtained in the presence of GBR12909; positive control: cocaine (IC50 = 8.5E-7 M) and methamphetamine (IC50 = 3.7E-7 M)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 1E-4 mol/l

Results

title comp. slightly inhibited re-uptake of dopamine

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 11 of 21

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 99.1percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>5-HT addition; 5 min at 37 deg C; scintillation counted

Further Details (Pharmacological Data)

non-specific uptake obtained in the presence of citalopram; positive control: cocaine (IC50 = 2.1E-6 M) and methamphetamine (IC50 = 4.0E-6 M); 5-HT: serotonin

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

7.9E-5 mol/l

Results

title comp. slightly inhibited re-uptake of 5-HT

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 12 of 21

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

20 mg/kg

Kind of Dosing (Pharmacological Data)

aqueous suspension; single dose

Method (Pharmacological Data)

urine collected separately from feces over 24 h period; samples analyzed by GC/MS or CE/MS/MS

Comment (Pharmacological Data)

Further metabolite(s)

Metabolite XRN (Pharmacological Data)

10342597; 10342598; 10344986

Metabolite (Pharmacological Data)

5-(2-amino-ethyl)-2-iodo-4-methoxy-phenol; 2-(2-amino-ethyl)-5-iodo-4-methoxy-phenol; (4-iodo-2,5-dimethoxy-phenyl)-acetic acid

Theobald, Denis S.; Puetz, Michael; Schneider, Erhard; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 41; nb. 7; (2006); p. 872 - 886, View in Reaxys

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13 of 21

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Wistar rat cerebral cortex 5-HT2A receptor

Sex

male

Method (Pharmacological Data)

membranes (10 mg wet wt of tissue) in Tris-HCl buffer pH 7.7 incubated with 1 nM <3H>ketanserin (spec. act.: 64.1 Ci/mmol) and title comp. at 25 deg C for 30 min; rapid filtration; counting of filter-retained radioactivity

Further Details (Pharmacological Data)

rat wt 250-300 g, brain cortex wt 150-200 g; membranes isolated from cortex homogenate by 2 centrifugation/resuspension cycles in Tris-HCl buffer pH 7.7; non-specific binding in presence of 10 μmol 5-HT

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

300 nmol/l

Claudi, Francesco; Scoccia, Loredana; Giorgioni, Gianfabio; Accorroni, Beatrice; Marucci, Gabriella; Gessi, Stefania; Siniscalchi, Anna; Borea, Pier Andrea; European Journal of Medicinal Chemistry; vol. 34; nb. 10; (1999); p. 843 - 852, View in Reaxys 14 of 21

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Wistar rat cerebral cortex 5-HT2C receptor

Sex

male

Method (Pharmacological Data)

membranes (10 mg wet wt of tissue) in Tris-HCl buffer pH 7.7 incubated with 1 nM <3H>mesulergine (spec. act.: 76 Ci/mmol) and title comp. at 25 deg C for 30 min; rapid filtration; counting of filter-retained radioactivity

Further Details (Pharmacological Data)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.5 nmol/l

Effect (Pharmacological Data)

antagonist

Species or Test-System (Pharmacological Data)

guinea-pig striatal slice 5-HT2A receptor

Concentration (Pharmacological Data)

3 - 30 μmol/l

Method (Pharmacological Data)

caudate nucleus slices (400 μm) incubated with 0.1 μM <3H>choline (81 Ci/mM), 30 min; superfused with Krebs solution containing 5-HT and title comp.; net increase in <3H> efflux by liquid scintillation counting of radioactivity of 5 min superfusates

Further Details (Pharmacological Data)

0.89 percent of net increase of <3H>choline efflux induced by 30 μM 5-HT added to the Krebs solution from the 45th min of superfusion

Results

negligible antagonistic action; net increase in <3H>choline efflux of 0.55 percent in presence of 30 μM 5-HT

Effect (Pharmacological Data)

agonist

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Species or Test-System (Pharmacological Data)

guinea-pig striatal slice 5-HT2A receptor

Concentration (Pharmacological Data)

30 μmol/l

Method (Pharmacological Data)

caudate nucleus slices (400 μm) incubated with 0.1 μM <3H>choline (81 Ci/mM), 30 min; superfused with Krebs solution containing title comp.; net increase in <3H> efflux by liquid scintillation counting of radioactivity of 5 min superfusates

Results

net increase in <3H>choline efflux of 0.11 percent (n=5)

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

rat stomach fundus 5-HT2B receptor

Type (Pharmacological Data)

apparent antagonist dissociation constant

Value of Type (Pharmacological Data)

> 10000 nmol/l

Results

full agonist, pD2 = 6.54 (compared to 5-HT: pD2 = 8.20)

Effect (Pharmacological Data)

on GABA release

Species or Test-System (Pharmacological Data)

Sprague Dawley rats

Sex

male

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

two i.p. inj. of para-chlorophenylalanine Me ester HCl in 200 mg/kg 12 h apart; 48 h later during superfusion experiments 20 2-min fractions collected

Exposure Period (Pharmacological Data)

40 min

Method (Pharmacological Data)

2x200 mg/kg of p-chlorophenylalanine Me ester HCl; rats decapitated ; brain removed; frontal cortex trimmed of striatal, thalamic, and piriform cortex tissue; cortical slices transferred in Krebs-Ringer (KR) bicarbonate; McIlwain tissue chopper used

Further Details (Pharmacological Data)

GABA neurotransmitter pool in slices labeled with exogenous <(3)H>GABA prior release exp.; slices transferred in superfusion apparatus; with 10 μM ketanserin; stimulated GABA release evoked by 40 mM K+ KR; tritium release; serotonin detd. by HPLC-EC

Results

complete loss in endogenous serotonin observed; without ketanserin no effect on stimulated GABA release; with ketanserine significant reduction in GABA release was observed

Cozzi; Nichols; European journal of pharmacology; vol. 309; nb. 1; (1996); p. 25 - 31, View in Reaxys 19 of 21

Effect (Pharmacological Data)

on GABA release

Species or Test-System (Pharmacological Data)

Sprague Dawley rats

Sex

male

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

20 2-min fractions collected

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Exposure Period (Pharmacological Data)

40 min

Method (Pharmacological Data)

rats decapitated; brain removed; frontal cortex trimmed of striatal, thalamic, and piriform cortex tissue; cortical slices transferred in Krebs-Ringer (KR) bicarbonate; McIlwain tissue chopper used

Further Details (Pharmacological Data)

GABA neurotransmitter pool in slices labeled with exogenous <(3)H>GABA prior release exp.; slices transferred in a superfusion apparatus; stimulated GABA release evoked by 40 mM K+ KR; tritium release measured

Results

title compd. had no effect on GABA release with or without K+ stimulation

Cozzi; Nichols; European journal of pharmacology; vol. 309; nb. 1; (1996); p. 25 - 31, View in Reaxys 20 of 21

Comment (Pharmacological Data)

drug discrimination data, ED50: 1.04 μmol/kg

Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.; Journal of Medicinal Chemistry; vol. 37; nb. 25; (1994); p. 4346 - 4351, View in Reaxys 21 of 21

Comment (Pharmacological Data)

radioligand binding, affinity for 5-HT2A/2C receptors using displacement of <125I>-(+/-)-DOI (to label the agonist high affinity state) and <3H>ketanserin (to label the agonist low affinity state) in rat frontal cortex homogenates

Effect (Ecotoxicology)

antagonist

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

Ca. 1E-12 - 1E-05 mol/l

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

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

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

pIC50

Value of Type (Ecotoxicology)

9.82 dimensionless

Results

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

Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 2 of 10

Effect (Ecotoxicology)

membrane current; induction of

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

100 nmol/l

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

cultured cells expressing rat 5-HT2A receptors voltage-clamped at membrane potential of -70 mV; cells superfused at 2 ml/min with title comp.; membrane currents recorded

Further Details (Ecotoxi- reference comp.: 5-hydroxytryptamine (5-HT) cology) Results

title comp. elicited small current amounting to 15 percent of 5-HT response (figure)

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Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 3 of 10

Effect (Ecotoxicology)

membrane current; induction of

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

100 nmol/l

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

cultured cells expressing rat 5-HT2C receptors voltage-clamped at membrane potential of -70 mV; cells superfused at 2 ml/min with title comp.; membrane currents recorded

Further Details (Ecotoxi- reference comp.: 5-hydroxytryptamine (5-HT) cology) Results

title comp. elicited small current amounting to 35 percent of 5-HT response (figure)

Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 4 of 10

Effect (Ecotoxicology)

antagonist

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

Ca. 1E-12 - 1E-05 mol/l

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

cultured cells expressing rat 5-HT2A receptors voltage-clamped at membrane potential of -70 mV; cells superfused with title comp. pre- or coapplied with 100 nmol/l of 5-HT; 5-HTevoked currents recorded

Further Details (Ecotoxi- 5-HT: 5-hydroxytryptamine cology) Results

title comp. behaved as antagonist to 5-HT2A; it concentration-dependently blocked 5-HTevoked current; preapplication increased magnitude of blockade ca. 100-fold (figure)

Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 5 of 10

Effect (Ecotoxicology)

antagonist

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

3 nmol/l

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

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

Further Details (Ecotoxi- 5-HT: 5-hydroxytryptamine cology) Results

title comp. antagonized 5-HT2A receptors; it blocked 5-HT-evoked currents (figure)

Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 6 of 10

Effect (Ecotoxicology)

antagonist

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

3 nmol/l

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

cultured cells expressing rat 5-HT2A receptors voltage-clamped at membrane potential of -70 mV; cells superfused with title comp. preapplied for 1 - 3 min prior to challenge with 100 nmol/l of 5-HT; changes in 5-HT-evoked currents recorded

Further Details (Ecotoxi- 5-HT: 5-hydroxytryptamine cology) Results

title comp. antagonized 5-HT2A receptors; it time-dependently blocked 5-HT-evoked currents (figure)

Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 7 of 10

Effect (Ecotoxicology)

membrane current; inhibition of

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

3 nmol/l

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

cultured cells expressing rat 5-HT2C receptors voltage-clamped at membrane potential of -70 mV; cells superfused with title comp. preapplied for 2 min prior to challenge with increasing concentrations of 5-HT; changes in 5-HT-evoked currents recorded

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

No effect

Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 8 of 10

Effect (Ecotoxicology)

membrane current; inhibition of

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

Ca. 1E-12 - 1E-05 mol/l

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

cultured cells expressing rat 5-HT2C receptors voltage-clamped at membrane potential of -70 mV; cells superfused with title comp. pre- or coapplied with 100 nmol/l of 5-HT; changes in 5-HT-evoked currents recorded

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

No effect

Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo; British Journal of Pharmacology; vol. 141; nb. 7; (2004); p. 1167 - 1174, View in Reaxys 9 of 10

Effect (Ecotoxicology)

membrane current; induction of

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

Ca. 1E-09 - 1E-06 mol/l

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

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

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

EC50

Value of Type (Ecotoxicology)

26 nmol/l

Results

title comp. concentration-dependently induced membrane current with Imax = 17 percent (table, figure)

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; HuidobroToro, J Pablo; British journal of pharmacology; vol. 136; nb. 4; (2002); p. 510 - 519, View in Reaxys 10 of 10

Effect (Ecotoxicology)

membrane current; induction of

Species or Test-System (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

Ca. 1E-09 - 1E-06 mol/l

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

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

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

EC50

Value of Type (Ecotoxicology)

71 nmol/l

Results

title comp. concentration-dependently induced membrane current with Imax = 44 percent (table, figure)

References

store under inert gas

Trachsel, Daniel; Nichols, David E.; Kidd, Stephanie; Hadorn, Marcel; Baumberger, Franz; Chemistry and Biodiversity; vol. 6; nb. 5; (2009); p. 692 - 704, View in Reaxys

Reaxys ID 10594974 View in Reaxys

2/4 Chemical Name: 2C- I; 4-iodo-2,5-dimethoxy-β-phenethylamine hydrochloride; 2,5-dimethoxy-4-iodophenethylamine hydrochloride; 4-iodo-2,5-dimethoxyphenethylamine hydrochloride Linear Structure Formula: C10H14INO2*ClH Molecular Formula: C10H14INO2*ClH Molecular Weight: 343.592 Type of Substance: isocyclic InChI Key: OTUXWIRPEPMONF-UHFFFAOYSA-N Note:

O NH 2 Cl

I O

Substance Label (2) Label References 2C-I

Theobald, Denis S.; Maurer, Hans H.; Biochemical Pharmacology; vol. 73; nb. 2; (2007); p. 287 - 297, View in Reaxys

25I

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 (7)

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1 of 7

Comment (Pharmacological Data)

Bioactivities present

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; Theobald, Denis S.; Maurer, Hans H.; Biochemical Pharmacology; vol. 73; nb. 2; (2007); p. 287 - 297, 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; Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.; ACS Chemical Neuroscience; vol. 5; nb. 3; (2014); p. 243 - 249, View in Reaxys 2 of 7

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 7

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

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

Method (Pharmacological Data)

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

Further Details (Pharmacological Data)

5-HT: 5-hydroxytryptamine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.62 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 7

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

NIH-3T3 cells expressing rat 5-HT2A receptor

Method (Pharmacological Data)

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

Further Details (Pharmacological Data)

5-HT: 5-hydroxytryptamine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

19.0 nmol/l

Results

intrinsic activity was 59 percent

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

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Method (Pharmacological Data)

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

Further Details (Pharmacological Data)

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

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.73 nmol/l

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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 6 of 7

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Method (Pharmacological Data)

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

Further Details (Pharmacological Data)

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

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

4.52 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 7 of 7

Effect (Pharmacological Data)

agonist

Species or Test-System (Pharmacological Data)

HEK-293 cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

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

Further Details (Pharmacological Data)

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

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2.54 nmol/l

Results

intrinsic activity was 82 percent

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

Reaxys ID 11306112 View in Reaxys 2H 2H

3/4

Chemical Name: 2-(4-iodo-2,5-di([2H3]methoxy)phenyl)ethylamine Linear Structure Formula: C10H8 (2)H6INO2 Molecular Formula: C10H14INO2 Molecular Weight: 313.084 InChI Key: PQHQBRJAAZQXHL-WFGJKAKNSA-N Note:

NH 2

I 2H

O 2H

Substance Label (1) Label References 8; <2H&6%>-2C-I Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

Solvents (NMR Spectro- CDCl3 scopy)

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Frequency (NMR Spectroscopy) [MHz]

300

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

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

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

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

13C

Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

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

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

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

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

Reaxys ID 26969028 View in Reaxys

4/4 Chemical Name: 4-iodo-2,5-dimethoxy-[13C6]-phenethylamine hydrochloride Linear Structure Formula: C4 (13)C6H14INO2*ClH Molecular Formula: C10H14INO2*ClH Molecular Weight: 349.526 InChI Key: OTUXWIRPEPMONF-QJPVZZEOSA-N Note:

O H 13C I

13C

13C 13CH

NH 2

HCl

Substance Label (1) Label References 6a

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

Melting Point (1) 1 of 1

Melting Point [°C]

244

Comment (Melting Point)

with decomposition

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

NMR Spectroscopy (2) 1 of 2

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

Coupling Nuclei

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

400

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

13C

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

100

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

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