N-isopropyl-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)propan-2-amine (5-MeO-DiPT) Substances (2) Details by Asch

Query Query

Results

Date

2 substances in Reaxys

2016-06-01 11h:39m:34s (EST)

1. Query O

Search as: As drawn

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Reaxys ID 482371 View in Reaxys

1/2 CAS Registry Number: 4021-34-5 Chemical Name: 5-Methoxy-N,N-diisopropyltryptamine; 5MeO-DIPT; diisopropyl-[2-(5-methoxy-indol-3-yl)-ethyl]-amine; Diisopropyl-<2-(5-methoxy-indol-3-yl)-ethyl>-amin; 3-(2-Diisopropylamino-ethyl)-5-methoxy-indol Linear Structure Formula: C17H26N2O Molecular Formula: C17H26N2O Molecular Weight: 274.406 Type of Substance: heterocyclic InChI Key: DNBPMBJFRRVTSJ-UHFFFAOYSA-N Note:

N O NH

Substance Label (3) Label References 5-MeO-DIPT

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, 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; Narimatsu, Shizuo; Yonemoto, Rei; Masuda, Kazufumi; Katsu, Takashi; Asanuma, Masato; Kamata, Tooru; Katagi, Munehiro; Tsuchihashi, Hitoshi; Kumamoto, Takuya; Ishikawa, Tsutomu; Naito, Shinsaku; Yamano, Shigeru; Hanioka, Nobumitsu; Biochemical Pharmacology; vol. 75; nb. 3; (2008); p. 752 - 760, View in Reaxys

5-MeO-DIPT; Foxy

Narimatsu, Shizuo; Yonemoto, Rei; Saito, Keita; Takaya, Kazuo; Kumamoto, Takuya; Ishikawa, Tsutomu; Asanuma, Masato; Funada, Masahiko; Kiryu, Kimio; Naito, Shinsaku; Yoshida, Yuzo; Yamamoto, Shigeo; Hanioka, Nobumitsu; Biochemical Pharmacology; vol. 71; nb. 9; (2006); p. 1377 - 1385, View in Reaxys

Desaty; Keglevic; Croatica Chemica Acta; vol. 36; (1964); p. 103,106, View in Reaxys

Derivative (2) Comment (Derivative)

References

Hydrochlorid: Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys C17H26N2O*HCl: F: 180-181grad, aus A.+Ae. Pikrat: C17H26N2O*C6 H3N3O7: Prep.: 4-Methoxy-phenylhydrazin-hydrochlorid, 25percentig. Essigsaeure, 4-Diisopropylamino-1,1diethoxy-butan; 80grad, 2.5h; F: 179-180grad, aus A.

Desaty; Keglevic; Croatica Chemica Acta; vol. 36; (1964); p. 103,106, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry) LCMS (Liquid chromatography mass spectrometry); Tandem mass spectrometry; Spectrum

Kim, Yoon; Kim, Un Yong; In, Moon Kyo; Lee, Jaeick; Kwon, Oh-Seung; Yoo, Hye Hyun; Bulletin of the Korean Chemical Society; vol. 32; nb. 4; (2011); p. 1158 - 1164, View in Reaxys

Pharmacological Data (36) 1 of 36

Comment (Pharmacological Data)

Bioactivities present

Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys; Desaty; Keglevic; Croatica Chemica Acta; vol. 36; (1964); p. 103,106, View in Reaxys; Narimatsu, Shizuo; Yonemoto, Rei; Saito, Keita; Takaya, Kazuo; Kumamoto, Takuya; Ishikawa, Tsutomu; Asanuma, Masato; Funada, Masahiko; Kiryu, Kimio; Naito, Shinsaku; Yoshida, Yuzo; Yamamoto, Shigeo; Hanioka, Nobumitsu; Biochemical Pharmacology; vol. 71; nb. 9; (2006); p. 1377 - 1385, View in Reaxys; Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada;

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Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, 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; Fantegrossi, William E.; Murnane, Kevin S.; Reissig, Chad J.; Biochemical Pharmacology; vol. 75; nb. 1; (2008); p. 17 - 33, 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; Narimatsu, Shizuo; Yonemoto, Rei; Masuda, Kazufumi; Katsu, Takashi; Asanuma, Masato; Kamata, Tooru; Katagi, Munehiro; Tsuchihashi, Hitoshi; Kumamoto, Takuya; Ishikawa, Tsutomu; Naito, Shinsaku; Yamano, Shigeru; Hanioka, Nobumitsu; Biochemical Pharmacology; vol. 75; nb. 3; (2008); p. 752 - 760, View in Reaxys; Kim, Yoon; Kim, Un Yong; In, Moon Kyo; Lee, Jaeick; Kwon, Oh-Seung; Yoo, Hye Hyun; Bulletin of the Korean Chemical Society; vol. 32; nb. 4; (2011); p. 1158 - 1164, View in Reaxys; Narimatsu, Shizuo; Kiryu, Kimio; Yonemoto, Rei; Yoshino, Manabu; Kobatake, Mitsuko; Kazamori, Daichi; Hagino, Saori; Masuda, Kazufumi; Katsu, Takashi; Asanuma, Masato; Kumamoto, Takuya; Ishikawa, Tsutomu; Funae, Yoshihiko; Yamano, Shigeru; Hanioka, Nobumitsu; Naito, Shinsaku; Chemico-Biological Interactions; vol. 172; nb. 1; (2008); p. 11 - 21, View in Reaxys; Rokitta; Fuhr; Current Drug Metabolism; vol. 11; nb. 2; (2010); p. 153 - 161, View in Reaxys; Meyer, Markus R.; Maurer, Hans H.; Current Drug Metabolism; vol. 11; nb. 5; (2010); p. 468 - 482, View in Reaxys; Niwa, Toshiro; Yamazaki, Hiroshi; Current Drug Metabolism; vol. 13; nb. 8; (2012); p. 1145 - 1159, View in Reaxys; Taylor; Duckles; Nelson; Journal of Pharmacology and Experimental Therapeutics; vol. 236; nb. 1; (1986); p. 118 - 125, View in Reaxys 2 of 36

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

20 mg/kg

Further Details (Pharmacological Data)

LC/MS/MS; mass of species: 250 - 280 g

Metabolite XRN (Pharmacological Data)

215153; 398238; 11248625

Metabolite (Pharmacological Data)

5-Hydroxy-N,N-diisopropyltryptamine; 5-Methoxy-N-isopropyltryptamine; 6-OH-5-MeODIPT

Kim, Yoon; Kim, Un Yong; In, Moon Kyo; Lee, Jaeick; Kwon, Oh-Seung; Yoo, Hye Hyun; Bulletin of the Korean Chemical Society; vol. 32; nb. 4; (2011); p. 1158 - 1164, View in Reaxys 3 of 36

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

liver microsomes of Wistar rat

Sex

male and female

Concentration (Pharmacological Data)

200 μmol/l

Method (Pharmacological Data)

microsomes from BNF-pretreated rats added to reaction mixture containing title comp., glucose-6-phosphate, NADPH; reaction stopped; centrifuged; supernatant collected; title comp. and metabolite levels determined by HPLC

Further Details (Pharmacological Data)

results compared with liver microsomes isolated from untreated male and female rats

Results

title comp. biotransformation was biphasic with low/high Km and Vmax values of 0.13/70.8 μM and 404/406 pmol/(min mg protein), respectively; fig., table

Metabolite XRN (Pharmacological Data)

215153

Metabolite (Pharmacological Data)

5-Hydroxy-N,N-diisopropyltryptamine

Narimatsu, Shizuo; Yonemoto, Rei; Masuda, Kazufumi; Katsu, Takashi; Asanuma, Masato; Kamata, Tooru; Katagi, Munehiro; Tsuchihashi, Hitoshi; Kumamoto, Takuya; Ishikawa, Tsutomu; Naito, Shinsaku; Yamano, Shigeru; Hanioka, Nobumitsu; Biochemical Pharmacology; vol. 75; nb. 3; (2008); p. 752 - 760, View in Reaxys 4 of 36

Effect (Pharmacological Data)

biotransformation

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Species or Test-System (Pharmacological Data)

liver microsomes of Wistar rat

Sex

male and female

Concentration (Pharmacological Data)

200 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

results compared with liver microsomes isolated from untreated male and female rats

Results

title comp. biotransformation was monophasic with Km and Vmax values of 288 μM and 3340 pmol/(min mg protein), respectively; fig., table

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

liver microsomes of Wistar rat

Sex

male and female

Concentration (Pharmacological Data)

200 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

results compared with liver microsomes isolated from untreated male and female rats

Results

title comp. biotransformation was monophasic with Km and Vmax values of 14.6 μM and 1400 pmol/(min mg protein), respectively; fig., table

Metabolite XRN (Pharmacological Data)

11248625

Metabolite (Pharmacological Data)

6-OH-5-MeO-DIPT

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

COS-7 cells

Concentration (Pharmacological Data)

Ca. 1 - 3000 μmol/l

Method (Pharmacological Data)

cells transfected or not with rSERT or rDAT treated with title comp. for 24 h; cell number assessed by WST-1; optical density measured using microplate reader at 450 nm

Further Details (Pharmacological Data)

rSERT: rat serotonin transporter; rDAT: rat dopamine transporter; WST-1: 2-(4-iodophenyl)-3-(4-nitro-phenyl)-5-(2,4-disulfo-phenyl)-2H-tetrazolium; 1-methyl-4-phenylpyridinium (MPP(1+)) used as positive control

Results

title comp. at ca. 300-3000 μmol/l sign. decreased viability of cells transfected or not with rSERT or rDAT in similar degree; no effect at <=100 μmol/l (figure)

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Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 7 of 36

Effect (Pharmacological Data)

transport; inhibition of

Species or Test-System (Pharmacological Data)

COS-7 cells

Concentration (Pharmacological Data)

Ca. 1 - 500 μmol/l

Method (Pharmacological Data)

cells expressing rDAT incubated with <3H>DA in presence of title comp. for 10 min at 37 deg C; radioactivity extracted with NaOH; measured by liquid scintillation spectrometry

Further Details (Pharmacological Data)

rDAT: rat dopamine transporter; DA: dopamine; cocaine used as positive control (IC50 = 1.05 μmol/l)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

167.47 μmol/l

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 8 of 36

Effect (Pharmacological Data)

transport; inhibition of

Species or Test-System (Pharmacological Data)

COS-7 cells

Concentration (Pharmacological Data)

Ca. 1 - 500 μmol/l

Method (Pharmacological Data)

cells expressing rSERT incubated with <3H>5-HT in presence of title comp. for 10 min at 37 deg C; radioactivity extracted with NaOH; measured by liquid scintillation spectrometry

Further Details (Pharmacological Data)

rSERT: rat serotonin transporter; 5-HT: serotonin; cocaine used as positive control (IC50 = 0.64 μmol/l)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

1.08 μmol/l

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 9 of 36

Effect (Pharmacological Data)

transport; inhibition of

Species or Test-System (Pharmacological Data)

COS-7 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

cells expressing rSERT pretreated without or with title comp.; incubated with <3H>5-HT in presence of title comp. for 5 min at 37 deg C; radioactivity extracted with NaOH; measured by liquid scintillation spectrometry; kinetics of 5-HT uptake examined

Further Details (Pharmacological Data)

rSERT: rat serotonin transporter; 5-HT: serotonin; cocaine and methamphetamine used as reference comp.

Results

title comp. sign. increased Km value from 0.589 to 0.915 μmol/l; no effect on Vmax value; effect comparable to that of cocaine, but not methamphetamine (table)

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 10 of 36

Effect (Pharmacological Data)

transport; effect on

Species or Test-System (Pharmacological Data)

COS-7 cells

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Concentration (Pharmacological Data)

300 μmol/l

Method (Pharmacological Data)

cells expressing rSERT preloaded with <3H>5-HT; treated with title comp. for 2 min at 37 deg C; released radioactivity measured by liquid scintillation spectrometry

Further Details (Pharmacological Data)

rSERT: rat serotonin transporter; 5-HT: serotonin; cocaine and methamphetamine used as reference comp.; further investigation in presence of methamphetamine

Comment (Pharmacological Data)

No effect

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 11 of 36

Effect (Pharmacological Data)

transport; effect on

Species or Test-System (Pharmacological Data)

COS-7 cells

Concentration (Pharmacological Data)

Ca. 1 - 500 μmol/l

Method (Pharmacological Data)

cells expressing mGAT1 incubated with <3H>GABA in presence of title comp. for 10 min at 37 deg C; radioactivity extracted with NaOH; measured by liquid scintillation spectrometry

Further Details (Pharmacological Data)

mGAT1: mouse GABA transporter 1; nipecotic acid used as positive control

Comment (Pharmacological Data)

No effect

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 12 of 36

Effect (Pharmacological Data)

transport; inhibition of

Species or Test-System (Pharmacological Data)

COS-7 cells

Concentration (Pharmacological Data)

Ca. 1 - 500 μmol/l

Method (Pharmacological Data)

cells expressing rNET incubated with <3H>NE in presence of title comp. for 10 min at 37 deg C; radioactivity extracted with NaOH; measured by liquid scintillation spectrometry

Further Details (Pharmacological Data)

rNET: rat norepinephrine transporter; NE: norepinephrine; cocaine used as positive control (IC50 = 0.5 μmol/l)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

43.60 μmol/l

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 13 of 36

Effect (Pharmacological Data)

transport; inhibition of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat cerebral cortex synaptosomes

Sex

male

Concentration (Pharmacological Data)

Ca. 1 - 500 μmol/l

Method (Pharmacological Data)

synaptosomes incubated with <3H>NE and title comp. for 5 min at 37 deg C in presence of GBR12935 plus paroxetine; filtered; NET activity determined by measuring radioactivity using liquid scintillation spectrometry

Further Details (Pharmacological Data)

NE: norepinephrine; NET: norepinephrine transporter; cocaine used as positive control (IC50 = 0.53 μmol/l)

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Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

10.5 μmol/l

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 14 of 36

Effect (Pharmacological Data)

transport; inhibition of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat striatal synaptosomes

Sex

male

Concentration (Pharmacological Data)

Ca. 1 - 500 μmol/l

Method (Pharmacological Data)

synaptosomes incubated with <3H>DA and title comp. for 5 min at 37 deg C in presence of nisoxetine plus paroxetine; filtered; DAT activity determined by measuring radioactivity using liquid scintillation spectrometry

Further Details (Pharmacological Data)

DA: dopamine; DAT: dopamine transporter; cocaine used as positive control (IC50 = 0.36 μmol/l)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

90.1 μmol/l

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 15 of 36

Effect (Pharmacological Data)

transport; inhibition of

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat striatal synaptosomes

Sex

male

Concentration (Pharmacological Data)

Ca. 1 - 500 μmol/l

Method (Pharmacological Data)

synaptosomes incubated with <3H>5-HT and title comp. for 5 min at 37 deg C in presence of gbr12935 plus nisoxetine; filtered; SERT activity determined by measuring radioactivity using liquid scintillation spectrometry

Further Details (Pharmacological Data)

5-HT: serotonin; SERT: serotonine transporter; cocaine used as positive control (IC50 = 0.9 μmol/l)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

1.80 μmol/l

Sogawa; Tagawa; Fujino; Ohyama; Asanuma; Funada; Kitayama; Toxicology Letters; vol. 170; nb. 1; (2007); p. 75 - 82, View in Reaxys 16 of 36

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 96.1percent

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

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Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

> 1E-4 mol/l

Results

title comp. slightly stimulated release of norepinephrine

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 17 of 36

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 96.1percent

Method (Pharmacological Data)

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

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. slightly stimulated release 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 18 of 36

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 96.1percent

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. slightly stimulated release 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 19 of 36

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 96.1percent

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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)

8.2E-6 mol/l

Results

title comp. relatively strongly inhibited re-uptake of norepinephrine; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 20 of 36

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

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 96.1percent

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)

6.5E-5 mol/l

Results

title comp. weakly inhibited dopamine re-uptake; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 21 of 36

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 96.1percent

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)

2.2E-6 mol/l

Results

title comp. relatively strongly inhibited re-uptake of 5-HT; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 22 of 36

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human liver microsomes

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Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

human microsomes and title comp. incubated in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA) for 5 - 10 min; then metabolites formed examined by HPLC, fluorescence excitation/emission wavelength, 280/340 nm

Further Details (Pharmacological Data)

control: vehicle; further investigations with CYP inhibitors: quinidine (CYP2D6), furafylline (CYP1A2), quercetin (CYP2C8), sulfaphenazol (CYP2C9), ketoconazole (CYP3A4), omeprazole (CYP2C19); CYP: cytochrome P450

Results

after incubation of title comp. with human liver microsomes two major metabolite 5-OHDIPT and 5-MeO-IPT (figure); title comp. O-demethylation mediated by CYP2D6, N-deisopropylation by CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP3A4

Metabolite XRN (Pharmacological Data)

215153; 398238

Metabolite (Pharmacological Data)

5-Hydroxy-N,N-diisopropyltryptamine; 5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human liver microsomes

Concentration (Pharmacological Data)

0.1 - 1000 μmol/l

Method (Pharmacological Data)

human microsomes and title comp. incubated for 5 - 10 min in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA); then metabolites formed examined by HPLC

Further Details (Pharmacological Data)

control: vehicle; Km and Vmax estimated using Michaelis-Menten and Eadie-Hofstee plots; O-demethylation: formation of 5-MeOH-DIPT; N-deisopropylation: formation of 5-MeO-IPT; CYP: cytochrome P450

Results

O-demethylation of title comp. was monophasic with Km and Vmax 5 μmol/l and 140 pmol/min/mg protein, resp.; N-deisopropylation was triphasic with Km 24, 260, and 1200 μmol/l and Vmax 25, 178, and 409 pmol/min/mg protein, resp.

Metabolite XRN (Pharmacological Data)

215153; 398238

Metabolite (Pharmacological Data)

5-Hydroxy-N,N-diisopropyltryptamine; 5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human recombinant CYP1A2 expressed in yeast cells

Concentration (Pharmacological Data)

0.1 - 1000 μmol/l

Method (Pharmacological Data)

yeast cells and title comp. incubated for 5 - 10 min in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA); then metabolites formed examined by HPLC; kinetic parameters analysed

Further Details (Pharmacological Data)

control: vehicle; Km and Vmax estimated using Michaelis-Menten and Eadie-Hofstee plots; CYP: cytochrome P450; O-demethylation: formation of 5-MeOH-DIPT; N-deisopropylation: formation of 5-MeO-IPT

Type (Pharmacological Data)

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Value of Type (Pharmacological Data)

263 μmol/l

Results

N-deisopropylation of title comp. by yeast cells was monophasic with Vmax = 9.4 pmol/min/ pmol CYP (table)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

recombinant human CYP1A2 expressed in yeast cells

Concentration (Pharmacological Data)

1 - 50 μmol/l

Method (Pharmacological Data)

5 pmol/l of enzyme and title comp. incubated in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA) for 5 - 10 min; then metabolites formed examined by HPLC, fluorescence excitation/emission wavelength, 280/340 nm

Further Details (Pharmacological Data)

control: vehicle; CYP: cytochrome P450

Results

incubation of title comp. with human CYP1A2 resulted in dose-dependent formation of 5MeO-IPT, but not 5-OH-DIPT metabolite (figure)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

recombinant human CYP2C8 expressed in yeast cells

Concentration (Pharmacological Data)

1 - 50 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

control: vehicle; CYP: cytochrome P450

Results

incubation of title comp. with human CYP2C8 expressed in yeast cells resulted in dosedependent formation of 5-MeO-IPT, but not 5-OH-DIPT metabolite (figure)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

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Species or Test-System (Pharmacological Data)

recombinant human CYP2C9 expressed in yeast cells

Concentration (Pharmacological Data)

1 - 50 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

control: vehicle; CYP: cytochrome P450

Results

incubation of title comp. with human CYP2C9 resulted in dose-dependent formation of 5MeO-IPT, but not 5-OH-DIPT metabolite (figure)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

recombinant human CYP2C19 expressed in yeast cells

Concentration (Pharmacological Data)

1 - 50 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

control: vehicle; CYP: cytochrome P450

Results

incubation of title comp. with human CYP2C19 expressed in yeast cells resulted in dosedependent formation of 5-MeO-IPT, but not 5-OH-DIPT metabolite (figure)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

recombinant human CYP2D6 expressed in yeast cells

Concentration (Pharmacological Data)

1 - 50 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

control: vehicle; CYP: cytochrome P450

Results

incubation of title comp. with human CYP2D6 resulted in dose-dependent formation of 5OH-DIPT metabolite and to a less extent of 5-MeO-IPT (figure)

Metabolite XRN (Pharmacological Data)

215153; 398238

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Metabolite (Pharmacological Data)

5-Hydroxy-N,N-diisopropyltryptamine; 5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

recombinant human CYP3A4 expressed in yeast cells

Concentration (Pharmacological Data)

1 - 50 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

control: vehicle; CYP: cytochrome P450

Comment (Pharmacological Data)

No effect

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

recombinant human CYP3A4 expressed in insect cells

Concentration (Pharmacological Data)

1 - 50 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

control: vehicle; CYP: cytochrome P450; further investigation with title comp. incubated with CYP3A4 coexpressed with cytochrome b5 in insect cells

Results

incubation of title comp. with CYP3A4 showed no detectable amounts of any of metabolities; however, when CYP3A4 was coexpressed with cytochrome b5 5-MeO-IPT, but not 5MeOH-DIPT, formed in considerable amounts (figure)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human recombinant CYP2D6 expressed in yeast cells

Concentration (Pharmacological Data)

0.1 - 1000 μmol/l

Method (Pharmacological Data)

yeast cells, expressing CYP2D6, and title comp. incubated for 5 - 10 min in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA), then metabolites formed examined by HPLC; kinetic parameters analysed

Further Details (Pharmacological Data)

control: vehicle; Km and Vmax estimated using Michaelis-Menten and Eadie-Hofstee plots; CYP: cytochrome P450; O-demethylation: formation of 5-MeOH-DIPT; N-deisopropylation: formation of 5-MeO-IPT

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Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.0 μmol/l

Results

O-demethylation of title comp. by yeast cells was monophasic with Vmax = 29.8 pmol/min/ pmol CYP (table); kinetic parameters for N-deisopropylation of title comp. were not calculated because of low activity

Metabolite XRN (Pharmacological Data)

215153

Metabolite (Pharmacological Data)

5-Hydroxy-N,N-diisopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human recombinant CYP2C8 expressed in yeast cells

Concentration (Pharmacological Data)

0.1 - 1000 μmol/l

Method (Pharmacological Data)

yeast cells, expressing CYP2C8, and title comp. incubated for 5 - 10 min in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA), then metabolites formed examined by HPLC; kinetic parameters analysed

Further Details (Pharmacological Data)

control: vehicle; Km and Vmax estimated using Michaelis-Menten and Eadie-Hofstee plots; CYP: cytochrome P450; O-demethylation: formation of 5-MeOH-DIPT; N-deisopropylation: formation of 5-MeO-IPT

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

291 μmol/l

Results

N-deisopropylation of title comp. by yeast cells was monophasic with Vmax = 1.7 pmol/min/ pmol CYP (table)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human recombinant CYP2C9 expressed in yeast cells

Concentration (Pharmacological Data)

0.1 - 1000 μmol/l

Method (Pharmacological Data)

yeast cells, expressing CYP2C9, and title comp. incubated for 5 - 10 min in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA), then metabolites formed examined by HPLC; kinetic parameters analysed

Further Details (Pharmacological Data)

control: vehicle; Km and Vmax estimated using Michaelis-Menten and Eadie-Hofstee plots; CYP: cytochrome P450; O-demethylation: formation of 5-MeOH-DIPT; N-deisopropylation: formation of 5-MeO-IPT

Type (Pharmacological Data)

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Value of Type (Pharmacological Data)

1663 μmol/l

Results

N-deisopropylation of title comp. by yeast cells was monophasic with Vmax = 4.2 pmol/min/ pmol CYP (table)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human recombinant CYP2C19 expressed in yeast cells

Concentration (Pharmacological Data)

0.1 - 1000 μmol/l

Method (Pharmacological Data)

yeast cells, expressing CYP2C19, and title comp. incubated for 5 - 10 min in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA), then metabolites formed examined by HPLC; kinetic parameters analysed

Further Details (Pharmacological Data)

control: vehicle; Km and Vmax estimated using Michaelis-Menten and Eadie-Hofstee plots; CYP: cytochrome P450; O-demethylation: formation of 5-MeOH-DIPT; N-deisopropylation: formation of 5-MeO-IPT

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

35 μmol/l

Results

N-deisopropylation of title comp. by yeast cells was monophasic with Vmax = 6.9 pmol/min/ pmol CYP (table)

Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human recombinant CYP3A4 and b5 coexpressed in yeast cells

Concentration (Pharmacological Data)

0.1 - 1000 μmol/l

Method (Pharmacological Data)

yeast cells, coexpressing CYP3A4 and cytochrome b5, and title comp. incubated for 5-10 min in presence of NADPH-generating system (1 mmol/l NADPH, 10 mmol/l MgCl2, 0.2 mmol/l EDTA), then metabolites formed examined by HPLC; kinetic parameters analysed

Further Details (Pharmacological Data)

control: vehicle; Km and Vmax estimated using Michaelis-Menten and Eadie-Hofstee plots; CYP: cytochrome P450; O-demethylation: formation of 5-MeOH-DIPT; N-deisopropylation: formation of 5-MeO-IPT

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

184 μmol/l

Results

N-deisopropylation of title comp. by yeast cells was monophasic with Vmax = 4.4 pmol/min/ pmol CYP (table)

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Metabolite XRN (Pharmacological Data)

398238

Metabolite (Pharmacological Data)

5-Methoxy-N-isopropyltryptamine

Reaxys ID 18865481 View in Reaxys

2/2 CAS Registry Number: 1174656-30-4 Chemical Name: 5-methoxy-N,N-diisopropyl-[α,α,β,β-d4]-tryptamine Linear Structure Formula: C17H22 (2)H4N2O Molecular Formula: C17H26N2O Molecular Weight: 278.374 InChI Key: DNBPMBJFRRVTSJ-LZMSFWOYSA-N Note:

N 2H

NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300.1

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray mol peak ionisation); HRMS (High resolution mass spectrometry)

References Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 429, View in Reaxys

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