1-(2,4,5-trimethoxyphenyl)propan-2-amine [TMA-2]

Query Query

Results

Date

6 substances in Reaxys

2016-06-19 14h:17m:05s (EST)

O NH 2

1. Query O O

Search as: As drawn

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Reaxys ID 2112181 View in Reaxys

1/6 CAS Registry Number: 1083-09-6 Chemical Name: 2,4,5-trimethoxyamphetamine; 2,4,5-Trimethoxyamphetamine; 1-methyl-2-(2,4,5-trimethoxy-phenyl)-ethylamine; 1-Methyl-2-(2,4,5-trimethoxy-phenyl)-aethylamin; 2-Amino-1-(2.4.5-trimethoxy-phenyl)-propan; 2,4,5-trimethoxyphenylisopropylamine; α-Methyl-β-(2,4,5-trimethoxy-phenyl)-ethylamin Linear Structure Formula: C12H19NO3 Molecular Formula: C12H19NO3 Molecular Weight: 225.288 Type of Substance: isocyclic InChI Key: TVSIMAWGATVNGK-UHFFFAOYSA-N Note:

O NH 2 O O

Substance Label (11) Label References TMA-2

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel; Biochemical Pharmacology; vol. 54; nb. 12; (1997); p. 1361 - 1369, View in Reaxys; Ewald, Andreas H.; Fritschi, Giselher; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 41; nb. 9; (2006); p. 1140 - 1148, View in Reaxys; Zaitsu, Kei; Katagi, Munehiro; Kamata, Hiroe; Kamata, Tooru; Shima, Noriaki; Miki, Akihiro; Iwamura, Tatsunori; Tsuchihashi, Hitoshi; Journal of Mass Spectrometry; vol. 43; nb. 4; (2008); p. 528 - 534, View in Reaxys; Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero; Chirality; vol. 25; nb. 10; (2013); p. 617 - 621, View in Reaxys

1b

Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon; Journal of Medicinal Chemistry; vol. 33; nb. 3; (1990); p. 1032 - 1036, View in Reaxys

(+/-)-2

Glennon; Young; Benington; Morin; Journal of Medicinal Chemistry; vol. 25; nb. 10; (1982); p. 1163 - 1168, View in Reaxys

14c

Borchardt,R.T. et al.; Journal of Medicinal Chemistry; vol. 19; (1976); p. 1201 - 1209, View in Reaxys

7, Tab.I

Barfknecht et al.; Journal of Medicinal Chemistry; vol. 18; (1975); p. 208,209, View in Reaxys

16

Bailey,K. et al.; Canadian Journal of Chemistry; vol. 49; (1971); p. 3143 - 3151, View in Reaxys

9, Tab.I

Ho,B.T. et al.; Journal of Medicinal Chemistry; vol. 13; (1970); p. 26 - 30, View in Reaxys

zu IIa

Shulgin,A.T.; Journal of Medicinal Chemistry; vol. 11; (1968); p. 186 - 187, View in Reaxys

No. 20(Table I)

Shulgin; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 445 - 446, View in Reaxys

III, TMA-2

Shulgin; Experientia; vol. 20; nb. 7; (1964); p. 366 - 367, View in Reaxys

(V)

Patent; Merck and Co.; Inc.; BE633963; (1962); Chem.Abstr.; vol. 61; nb. 6953e; (1964), View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product Derivative (4) Comment (Derivative)

Patent; Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.; US2007/27208; (2007); (A1) English, View in Reaxys References

Komplex: 2,4,5Trimethoxyamphetamin*FMN; Abs. Sp., K.

Sung; Parker; Zeitschrift fuer Naturforschung, C: Journal of Biosciences; vol. 29; (1974); p. 122,124, View in Reaxys

Komplex: 2,4,5Trimethoxyamphetamin*FAD; thermodynamische Parameter

Sung; Parker; Zeitschrift fuer Naturforschung, C: Journal of Biosciences; vol. 29; (1974); p. 122,124, View in Reaxys

Hydrochlorid, F: 181grad

Shulgin; Experientia; vol. 20; nb. 7; (1964); p. 366 - 367, View in Reaxys

HCl-Salz: F: Patent; Merck and Co.; Inc.; BE633963; (1962); Chem.Abstr.; vol. 61; nb. 6953e; (1964), View in Reaxys 186.5 - 187.2grad Chromatographic Data (1)

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Chromatographic data

References

CE (Capillar electrophoresis)

Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero; Chirality; vol. 25; nb. 10; (2013); p. 617 - 621, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Sung; Parker; Zeitschrift fuer Naturforschung, C: Journal of Biosciences; vol. 29; (1974); p. 122,124, View in Reaxys

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

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Barfknecht et al.; Journal of Medicinal Chemistry; vol. 18; (1975); p. 208,209, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

1H

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

300

Zaitsu, Kei; Katagi, Munehiro; Kamata, Hiroe; Kamata, Tooru; Shima, Noriaki; Miki, Akihiro; Iwamura, Tatsunori; Tsuchihashi, Hitoshi; Journal of Mass Spectrometry; vol. 43; nb. 4; (2008); p. 528 - 534, View in Reaxys 2 of 2

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

1H

Bailey,K. et al.; Canadian Journal of Chemistry; vol. 49; (1971); p. 3143 - 3151, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Zaitsu, Kei; Katagi, Munehiro; Kamata, Hiroe; Kamata, Tooru; Shima, Noriaki; Miki, Akihiro; Iwamura, Tatsunori; Tsuchihashi, Hitoshi; Journal of Mass Spectrometry; vol. 43; nb. 4; (2008); p. 528 - 534, View in Reaxys

Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Fluorescence

Smythies et al.; Experientia; vol. 27; (1971); p. 62,63, View in Reaxys

Other Spectroscopic Methods (1) Description (Oth- References er Spectroscopic Methods) Photoelectron spectrum

Domelsmith, L. N.; Eaton, Thomas A.; Houk, K. N.; Anderson, G. M.; Glennon, R. A.; et al.; Journal of Medicinal Chemistry; vol. 24; nb. 12; (1981); p. 1414 - 1421, View in Reaxys

Pharmacological Data (14) 1 of 14

Comment (Pharmacological Data)

Bioactivities present

Bailey,K. et al.; Canadian Journal of Chemistry; vol. 49; (1971); p. 3143 - 3151, View in Reaxys; Shulgin; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 445 - 446, View in Reaxys; Shulgin,A.T.; Journal of Medicinal Chemistry; vol. 11; (1968); p. 186 - 187, View in Reaxys; Ho,B.T. et al.; Journal of Medicinal Chemistry; vol. 13; (1970); p. 26 - 30, View in Reaxys; Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111, View in Reaxys; Borchardt,R.T. et al.; Journal of Medicinal Chemistry; vol. 19; (1976); p. 1201 - 1209, View in Reaxys; Glennon; Liebowitz; Mack; Journal of Medicinal Chemistry; vol. 21; nb. 8; (1978); p. 822 - 825, View in Reaxys; Patent; Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.; US2007/27208; (2007); (A1) English, View in Reaxys; Bruckner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 138; (1933); p. 268,270,

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View in Reaxys; Barfknecht et al.; Journal of Medicinal Chemistry; vol. 18; (1975); p. 208,209, View in Reaxys; Shulgin; Experientia; vol. 20; nb. 7; (1964); p. 366 - 367, View in Reaxys; Sung; Parker; Zeitschrift fuer Naturforschung, C: Journal of Biosciences; vol. 29; (1974); p. 122,124, View in Reaxys; Patent; Merck and Co.; Inc.; BE633963; (1962); Chem.Abstr.; vol. 61; nb. 6953e; (1964), View in Reaxys; Smythies et al.; Experientia; vol. 27; (1971); p. 62,63, View in Reaxys; Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon; Journal of Medicinal Chemistry; vol. 33; nb. 3; (1990); p. 1032 - 1036, View in Reaxys; Domelsmith, L. N.; Eaton, Thomas A.; Houk, K. N.; Anderson, G. M.; Glennon, R. A.; et al.; Journal of Medicinal Chemistry; vol. 24; nb. 12; (1981); p. 1414 - 1421, View in Reaxys; Glennon; Liebowitz; Anderson III; Journal of Medicinal Chemistry; vol. 23; nb. 3; (1980); p. 294 299, View in Reaxys; Glennon; Young; Benington; Morin; Journal of Medicinal Chemistry; vol. 25; nb. 10; (1982); p. 1163 - 1168, View in Reaxys; Clare, Brian W.; Journal of Medicinal Chemistry; vol. 41; nb. 20; (1998); p. 3845 3856, View in Reaxys; Peddi, Srinivas; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 15; (2003); p. 2565 - 2568, View in Reaxys; Altun, Ahmet; Golcuk, Kurtulus; Kumru, Mustafa; Jalbout, Abraham F.; Bioorganic and Medicinal Chemistry; vol. 11; nb. 18; (2003); p. 3861 - 3868, View in Reaxys; Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel; Biochemical Pharmacology; vol. 54; nb. 12; (1997); p. 1361 1369, View in Reaxys; Thakur, Mamta; Thakur, Abhilash; Khadikar, Padmakar V.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 4; (2004); p. 825 - 831, View in Reaxys; Ewald, Andreas H.; Fritschi, Giselher; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 41; nb. 9; (2006); p. 1140 - 1148, 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; Zaitsu, Kei; Katagi, Munehiro; Kamata, Hiroe; Kamata, Tooru; Shima, Noriaki; Miki, Akihiro; Iwamura, Tatsunori; Tsuchihashi, Hitoshi; Journal of Mass Spectrometry; vol. 43; nb. 4; (2008); p. 528 - 534, View in Reaxys; Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6808 - 6828, View in Reaxys; Blaazer, Antoni R.; Smid, Pieter; Kruse, Chris G.; ChemMedChem; vol. 3; nb. 9; (2008); p. 1299 - 1309, View in Reaxys; Barfknecht; Nichols; Dunn III; Journal of Medicinal Chemistry; vol. 18; nb. 2; (1975); p. 208 - 210, View in Reaxys; Aldous; Barrass; Brewster; Buxton; Green; Pinder; Rich; Skeels; Tutt; Journal of Medicinal Chemistry; vol. 17; nb. 10; (1974); p. 1100 - 1111, View in Reaxys; Kier; Hall; Journal of Medicinal Chemistry; vol. 20; nb. 12; (1977); p. 1631 - 1636, View in Reaxys; Westkaemper, Richard B; Glennon, Richard A; Current topics in medicinal chemistry; vol. 2; nb. 6; (2002); p. 575 - 598, View in Reaxys; Glennon; Raghupathi; Bartyzel; Teitler; Leonhardt; Journal of Medicinal Chemistry; vol. 35; nb. 4; (1992); p. 734 - 740, View in Reaxys; Clare; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 687 - 702, View in Reaxys; Titeler; Lyon; Glennon; Psychopharmacology; vol. 94; nb. 2; (1988); p. 213 - 216, View in Reaxys; Glennon; Journal of Medicinal Chemistry; vol. 30; nb. 1; (1987); p. 1 - 12, View in Reaxys; Shannon; Battaglia; Glennon; Titeler; European journal of pharmacology; vol. 102; nb. 1; (1984); p. 23 - 29, View in Reaxys; Domelsmith; Eaton; Houk; Anderson III; Glennon; Shulgin; Castagnoli Jr.; Kollman; Journal of Medicinal Chemistry; vol. 24; nb. 12; (1981); p. 1414 - 1421, View in Reaxys; Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero; Chirality; vol. 25; nb. 10; (2013); p. 617 - 621, View in Reaxys; M.A. Davis; Annual reports in medicinal chemistry; vol. 4; (1968); p. 13 - 27, View in Reaxys; S.P.Gupta; Chemical reviews; vol. 89; nb. 8; (1989); p. 1765 - 1800, View in Reaxys; SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL; Chemical reviews; vol. 83; nb. 6; (1983); p. 633 - 649, View in Reaxys 2 of 14

Effect (Pharmacological Data)

[3H]ketanserin binding; inhibition of

Species or Test-System (Pharmacological Data)

NIH3T3 cell; genetically modified/infected with: 5-HT2A receptor

Further Details (Pharmacological Data)

Ki related to: 5-HT2A receptor

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

1200 nmol/l

Location

supporting information

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6808 - 6828, View in Reaxys 3 of 14

Effect (Pharmacological Data)

[3H]ketanserin binding; inhibition of

Species or Test-System (Pharmacological Data)

NIH3T3 cell; genetically modified/infected with: 5-HT2A receptor

Results

molecular target: 5-HT2A receptor

Location

supporting information

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6808 - 6828, View in Reaxys

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4 of 14

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 98.6percent

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.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 5 of 14

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 98.6percent

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 6 of 14

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 98.6percent

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

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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 7 of 14

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 98.6percent

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)

> 1E-4 mol/l

Results

title comp. slightly inhibited re-uptake 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 8 of 14

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 98.6percent

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 9 of 14

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 98.6percent

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

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Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 1E-4 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 10 of 14

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

Wistar rat

Route of Application

peroral

Concentration (Pharmacological Data)

20 mg/kg

Kind of Dosing (Pharmacological Data)

suspension in water

Method (Pharmacological Data)

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

Comment (Pharmacological Data)

Further metabolite(s)

Metabolite XRN (Pharmacological Data)

10442697; 2582827; 10438821

Metabolite (Pharmacological Data)

N-acetyl-2,4,5-trimethoxyamphetamine; 2,4,5-Trimethoxyphenylacetone; 1-methyl-2(2,4,5-trimethoxyphenyl)ethyl acetate

Ewald, Andreas H.; Fritschi, Giselher; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 41; nb. 9; (2006); p. 1140 - 1148, View in Reaxys 11 of 14

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

IIBCE rat brain mitochondrial monoamine oxidase B

Sex

male

Concentration (Pharmacological Data)

Ca. 10 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

in distilled water

Method (Pharmacological Data)

MAO-B activity determined by HPLC with electrochemical detection after incubation with selective substrate of DMAPEA in presence of title comp. at 37 deg C for 5 min, pH 7.4; DMAPEA and its MAO-B metabolite DMAPAA used to calculate MAO-B activity

Further Details (Pharmacological Data)

MAO-B = monoamine oxidase B; DMAPEA = 4-dimethylaminophenethylamine, 5 μmol/l; DMAPAA = 4-dimethylaminophenylacetic acid

Comment (Pharmacological Data)

No effect

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel; Biochemical Pharmacology; vol. 54; nb. 12; (1997); p. 1361 - 1369, View in Reaxys 12 of 14

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

IIBCE rat brain mitochondrial monoamine oxidase A

Sex

male

Concentration (Pharmacological Data)

Ca. 1 - 100 μmol/l

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Kind of Dosing (Pharmacological Data)

in distilled water

Method (Pharmacological Data)

MAO-A activity determined by HPLC with electrochemical detection after incubation with selective substrate of 5-HT in presence of title comp. at 37 deg C for 10 min, pH 7.4; 5-HT and its MAO-A metabolite 5-HIAA used to calculate MAO-A activity

Further Details (Pharmacological Data)

MAO-A = monoamine oxidase A; 5-HT = serotonin, 2.5 μmol/l; 5-HIAA = 5-hydroxyindoleacetic acid; further studies with title comp. preincubation up to 60 min

Results

dose-, but not preincubation time-dependent effect (no effect at concentrations < 10 μmol/l, at 100 μmol/l ca. 25 percent inhibition observed)

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel; Biochemical Pharmacology; vol. 54; nb. 12; (1997); p. 1361 - 1369, View in Reaxys 13 of 14

Comment (Pharmacological Data)

5-HT2 serotonin antagonist activity

Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon; Journal of Medicinal Chemistry; vol. 33; nb. 3; (1990); p. 1032 - 1036, View in Reaxys 14 of 14

Comment (Pharmacological Data)

the serotonin (5HT) receptor affinities, human hallucinogen, ED50= 3.59 mg/kg

Glennon; Young; Benington; Morin; Journal of Medicinal Chemistry; vol. 25; nb. 10; (1982); p. 1163 - 1168, View in Reaxys

Reaxys ID 3729264 View in Reaxys

2/6 CAS Registry Number: 15995-72-9 Chemical Name: 2,4,5-Trimethoxyamphetamine hydrochloride; (+/-)-1-(2,4,5-trimethoxyphenyl)-2-aminopropane hydrochloride; (+/-)1-(2,4,5-trimethoxyphenyl)-2-aminopropane hydrochloride; 1-(2,4,5-trimethoxyphenyl)propan-2-amine hydrochloride; 1methyl-2-(2,4,5-trimethoxy-phenyl)-ethylamine; hydrochloride; 1-Methyl-2-(2,4,5-trimethoxy-phenyl)-aethylamin; Hydrochlorid; 2,4,5-Trimethoxy-amphetamin-hydrochlorid Linear Structure Formula: C12H19NO3*ClH Molecular Formula: C12H19NO3*ClH Molecular Weight: 261.749 Type of Substance: isocyclic InChI Key: JHYCECCYAFOEDA-UHFFFAOYSA-N Note:

O NH 2 Cl

H

O O

Substance Label (6) Label References TMA

Nelson; Lucaites; Wainscott; Glennon; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 359; nb. 1; (1999); p. 1 - 6, View in Reaxys

TMA-2

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels; Naunyn-Schmiedeberg's archives of pharmacology; vol. 354; nb. 5; (1996); p. 579 - 585, View in Reaxys

TMA-2 hydrochloride

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 89; nb. 3; (1992); p. 669 - 680, View in Reaxys

4

Knittel, James J.; Makriyannis, Alexandros; Journal of Medicinal Chemistry; vol. 24; nb. 7; (1981); p. 906 909, View in Reaxys

35

Bailey,K. et al.; Canadian Journal of Chemistry; vol. 49; (1971); p. 3143 - 3151, View in Reaxys

IIa

Shulgin,A.T.; Journal of Medicinal Chemistry; vol. 11; (1968); p. 186 - 187, View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

190 - 192

Solvent (Melting Point)

propan-2-ol

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 89; nb. 3; (1992); p. 669 - 680, View in Reaxys

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2 of 3

Melting Point [°C]

181

Shulgin; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 445 - 446, View in Reaxys; Shulgin,A.T.; Journal of Medicinal Chemistry; vol. 11; (1968); p. 186 - 187, View in Reaxys 3 of 3

Melting Point [°C]

187

Solvent (Melting Point)

ethyl acetate; ethanol

Bruckner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 138; (1933); p. 268,270, View in Reaxys Conformation (1) Object of Investi- References gation Conformation

Knittel, James J.; Makriyannis, Alexandros; Journal of Medicinal Chemistry; vol. 24; nb. 7; (1981); p. 906 909, View in Reaxys

NMR Spectroscopy (5) 1 of 5

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

1H

Solvents (NMR Spectro- D2O scopy) Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 89; nb. 3; (1992); p. 669 - 680, View in Reaxys 2 of 5

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- D2O scopy) Comment (NMR Spectroscopy)

1H-1H

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 89; nb. 3; (1992); p. 669 - 680, View in Reaxys 3 of 5

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

13C

Solvents (NMR Spectro- D2O scopy) Temperature (NMR Spectroscopy) [°C]

30

Knittel, James J.; Makriyannis, Alexandros; Journal of Medicinal Chemistry; vol. 24; nb. 7; (1981); p. 906 - 909, View in Reaxys 4 of 5

Description (NMR Spec- Spin-lattice relaxation time (T1) troscopy) Knittel, James J.; Makriyannis, Alexandros; Journal of Medicinal Chemistry; vol. 24; nb. 7; (1981); p. 906 - 909, View in Reaxys

5 of 5

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

1H

Bailey,K. et al.; Canadian Journal of Chemistry; vol. 49; (1971); p. 3143 - 3151, View in Reaxys Pharmacological Data (8) 1 of 8

Comment (Pharmacological Data)

Bioactivities present

Bailey,K. et al.; Canadian Journal of Chemistry; vol. 49; (1971); p. 3143 - 3151, View in Reaxys; Shulgin; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 445 - 446, View in Reaxys; Shulgin,A.T.; Journal of Medicinal Chemistry; vol. 11; (1968); p. 186 - 187, View in Reaxys; Glennon; Liebowitz; Mack; Journal of Medicinal Chemistry; vol.

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21; nb. 8; (1978); p. 822 - 825, View in Reaxys; Bruckner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 138; (1933); p. 268,270, View in Reaxys; Knittel, James J.; Makriyannis, Alexandros; Journal of Medicinal Chemistry; vol. 24; nb. 7; (1981); p. 906 - 909, View in Reaxys; Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 89; nb. 3; (1992); p. 669 - 680, View in Reaxys; Nelson; Lucaites; Wainscott; Glennon; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 359; nb. 1; (1999); p. 1 - 6, View in Reaxys; Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels; Naunyn-Schmiedeberg's archives of pharmacology; vol. 354; nb. 5; (1996); p. 579 - 585, View in Reaxys; Shulgin; Journal of medicinal chemistry; vol. 11; nb. 1; (1968); p. 186 - 187, View in Reaxys; Glennon, Richard A.; Dukat, Malgorzata; Grella, Brian; Hong, Seoung-Soo; Costantino, Luca; Teitler, Milt; Smith, Carol; Egan, Chris; Davis, Katherine; Mattson, Mariena V.; Drug and Alcohol Dependence; vol. 60; nb. 2; (2000); p. 121 - 132, View in Reaxys; Reyes-Parada, Miguel; Scorza, Cecilia; Romero, Veronica; Silveira, Rodolfo; Medina, Jorge H.; Andrus, Danice; Nichols, David E.; Cassels, Bruce K.; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 354; nb. 5; (1996); p. 579 - 585, View in Reaxys; Knittel; Makriyannis; Journal of Medicinal Chemistry; vol. 24; nb. 7; (1981); p. 906 - 909, View in Reaxys 2 of 8

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

membrane preparation of human 5-HT2A receptors

Method (Pharmacological Data)

suspension-grown AV12 cells stably transformed with human 5-HT2A receptors; receptors labeled with <125I>1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine; determination of nonspecific binding

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

57.9 mmol/l

Nelson; Lucaites; Wainscott; Glennon; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 359; nb. 1; (1999); p. 1 - 6, View in Reaxys 3 of 8

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

membrane preparation of rat 5-HT2B receptors

Method (Pharmacological Data)

suspension-grown AV12 cells stably transformed with rat 5-HT2B receptors; receptors labeled with <3H>serotonin; determination of non-specific binding

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

187 nmol/l

Nelson; Lucaites; Wainscott; Glennon; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 359; nb. 1; (1999); p. 1 - 6, View in Reaxys 4 of 8

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

membrane preparation of human 5-HT2C receptors

Method (Pharmacological Data)

suspension-grown AV12 cells stably transformed with human 5-HT2C receptors; receptors labeled with <125I>1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine; determination of nonspecific binding

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

87.7 nmol/l

Nelson; Lucaites; Wainscott; Glennon; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 359; nb. 1; (1999); p. 1 - 6, View in Reaxys 5 of 8

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

membrane preparation of human 5-HT2B receptors

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Method (Pharmacological Data)

suspension-grown AV12 cells stably transformed with human 5-HT2B receptors; receptors labeled with <3H>serotonin; determination of non-specific binding

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

307 nmol/l

Nelson; Lucaites; Wainscott; Glennon; Naunyn-Schmiedeberg's Archives of Pharmacology; vol. 359; nb. 1; (1999); p. 1 - 6, View in Reaxys 6 of 8

Effect (Pharmacological Data)

behavioural symptoms

Species or Test-System (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

30 μmol/kg

Exposure Period (Pharmacological Data)

30 min

Method (Pharmacological Data)

rats 200-240 g; motor activity, forepaw treading, hindlimb abduction, flat body posture observed

Results

induced some symptoms of serotonergic syndrome: flat body posture, decrease of motor activity; numerical table, diagram

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels; Naunyn-Schmiedeberg's archives of pharmacology; vol. 354; nb. 5; (1996); p. 579 - 585, View in Reaxys 7 of 8

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat brain 5-HT1A receptors

Method (Pharmacological Data)

frontal cortex or hippocampal homogenates preincubated with <3H>8-OH-DPAT, then with var. conc. title comp. 15 min, 37 deg C (displacement study); scintillation counting

Further Details (Pharmacological Data)

<3H>8-OH-DPAT bound to single site, Bmax: 110 fmol/mg protein, KD 0.67 nM; specific binding defined as displaceable with 10 μM 5-HT

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

26800 nmol/l

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels; Naunyn-Schmiedeberg's archives of pharmacology; vol. 354; nb. 5; (1996); p. 579 - 585, View in Reaxys 8 of 8

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

Sprague-Dawley rat brain 5-HT2A/2C receptors

Method (Pharmacological Data)

frontal cortex or hippocampal homogenates preincubated with <3H>ketanserin, then with var. conc. title comp. 15 min, 37 deg C (displacement study); scintillation counting

Further Details (Pharmacological Data)

<3H>ketanserin bound to single site, Bmax: 180 fmol/mg protein, KD 0.83 nM; specific binding defined as displaceable with 10 μM cinanserin

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

1112 nmol/l

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels; Naunyn-Schmiedeberg's archives of pharmacology; vol. 354; nb. 5; (1996); p. 579 - 585, View in Reaxys

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Reaxys ID 6793153 View in Reaxys

3/6 Chemical Name: (-)-3-(2,4,5-Trimethoxyphenyl)-isopropylamin Linear Structure Formula: C12H19NO3 Molecular Formula: C12H19NO3 Molecular Weight: 225.288 Type of Substance: isocyclic InChI Key: TVSIMAWGATVNGK-MRVPVSSYSA-N Note:

O NH 2 H O O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111, View in Reaxys; Deeb, Omar; Clare, Brian W.; Chemical Biology and Drug Design; vol. 71; nb. 4; (2008); p. 352 - 362, View in Reaxys

Reaxys ID 6793152 View in Reaxys

4/6 Chemical Name: (+)-3-(2,4,5-Trimethoxyphenyl)-isopropylamin Linear Structure Formula: C12H19NO3 Molecular Formula: C12H19NO3 Molecular Weight: 225.288 Type of Substance: isocyclic InChI Key: TVSIMAWGATVNGK-QMMMGPOBSA-N Note:

O NH 2 H O O

Reaxys ID 6796082 View in Reaxys

5/6 Linear Structure Formula: C12H19NO3*ClH Molecular Formula: C12H19NO3*ClH Molecular Weight: 261.749 Type of Substance: isocyclic InChI Key: JHYCECCYAFOEDA-QRPNPIFTSA-N Note:

O NH 2 H

Cl

H

O O

Melting Point (1) 1 of 1

Melting Point [°C]

163

Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

4 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

18.8

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

25

Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111, View in Reaxys

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Reaxys ID 6796083 View in Reaxys

6/6 Linear Structure Formula: C12H19NO3*ClH Molecular Formula: C12H19NO3*ClH Molecular Weight: 261.749 Type of Substance: isocyclic InChI Key: JHYCECCYAFOEDA-DDWIOCJRSA-N Note:

O NH 2 H

Cl

H

O O

Melting Point (1) 1 of 1

Melting Point [°C]

159

Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

4 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-20

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

25

Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111, View in Reaxys

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