Reaxys
PubChem
eMolecules
Reactions (7)
Substances (3)
Structure
Citations (10)
N° of preparations All Preps | All Reactions
Structure/Compound Data Chemical Name: N-hydroxy-3,4-methylenedioxyamphetamine Reaxys Registry Number: 4804638
CAS Registry Number: 74698-47-8 Type of Substance: heterocyclic Molecular Formula: C10H13NO3
Linear Structure Formula: C10H13NO3
Molecular Weight: 195.218 InChI Key: FNDCTJYFKOQGTL-UHFFFAOYSA-N
1
3 prep out of 6 reactions.
Synthesize | Hide Details Find similar Chemical Names and Synonyms N-hydroxy-3,4-methylenedioxyamphetamine, N-Hydroxy-3,4-methylenedioxyamphetamine, N-Hydroxy-3,4-methylendioxyphenylisopropylamin Identification Patent-Specific Data (1) Prophetic Compound
Reference
prophetic product
Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.
Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text Show Details
Derivative (2) Derivative
Reference
Available Data
N° of ref.
Identification Physical Data (1) Spectra (1) Bioactivity (3)
9
3,4-methylenedioxy-N-hydroxyamphetamine hydrochloride; C12H12F3NO4
De Boer; Tan; Gorter; Van de Wal; Kettenes-van den Bosch; De Bruijn; Maes
Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 - 1246 Title/Abstract Full Text View citing articles Show Details
3,4-methylenedioxy-N-hydroxyamphetamine hydrochloride
Braun; Shulgin
Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details
Physical Data Melting Point (1) Melting Point
Solvent (Melting Point)
Reference
94 - 95 °C
propan-2-ol
Braun; Shulgin
Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details
Spectra IR Spectroscopy (1) Description (IR Spectroscopy)
Solvent (IR Spectroscopy)
Comment (IR Spectroscopy)
Reference
Bands
paraffin
3135 - 3040 cm**(-1)
Braun; Shulgin
Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Reference
Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.
Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text Show Details
Fukuto; Kumagai; Cho
Journal of Medicinal Chemistry, 1991 , vol. 34, # 9 p. 2871 - 2876 Title/Abstract Full Text View citing articles Show Details
Braun; Shulgin
Arzneimittel-Forschung, 1980 , vol. 30, # 5 p. 825 - 830 Title/Abstract Full Text View citing articles Show Details
Braun; Shulgin
Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details
De Boer; Tan; Gorter; Van de Wal; Kettenes-van den Bosch; De Bruijn; Maes
Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 - 1246 Title/Abstract Full Text View citing articles Show Details
Clare, Brian W.
Journal of Medicinal Chemistry, 1998 , vol. 41, # 20 p. 3845 - 3856 Title/Abstract Full Text View citing articles Show Details
Amutha, Chinnadurai; Muthusubramanian, Shanmugam
Synthetic Communications, 2008 , vol. 38, # 3 p. 328 - 337 Title/Abstract Full Text View citing articles Show Details
Wellendorph; Goodman; Burstein; Nash; Brann; Weiner
Neuropharmacology, 2002 , vol. 42, # 7 p. 929 - 940 Title/Abstract Full Text View citing articles Show Details
Braun; Shulgin
Arzneimittel-Forschung/Drug Research, 1980 , vol. 30, # 5 p. 825 - 830 Title/Abstract Full Text View citing articles Show Details
2 of 3
3 of 3
Comment (Pharmacological Data)
analgetic potency, influence on motor activity (male NMRI-mouse, doses: 100 mg/kg, 20 mg/kg, 10 mg/kg, p.o.); phychotomimetic potency (man and woman, dose 80-120 mg, p.o.)
Reference
Braun; Shulgin
Arzneimittel-Forschung, 1980 , vol. 30, # 5 p. 825 - 830 Title/Abstract Full Text View citing articles Show Details
Comment (Pharmacological Data)
central stimulation activity: psychotomimetic activity (human)
Reference
Braun; Shulgin
Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details
Chemical Name: 3,4-methylenedioxy-N-hydroxyamphetamine hydrochloride Reaxys Registry Number: 6879804
Type of Substance: heterocyclic Molecular Formula: C10H13NO3*ClH Linear Structure Formula: C10H13NO3*HCl Molecular Weight: 231.679 InChI Key: DMBCJQVFXIKFJX-UHFFFAOYSA-N
1 prep out of 1 reactions.
Identification Physical Data (1) Spectra (3) Bioactivity (5)
3
2
Synthesize | Hide Details Find similar Chemical Names and Synonyms 3,4-methylenedioxy-N-hydroxyamphetamine hydrochloride Identification Substance Label (1) Label
Reference
MDOH
Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details
Physical Data Melting Point (1) Melting Point
Reference
149 - 150 °C
Braun; Shulgin
Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details
Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Solvents (NMR Spectroscopy)
Chemical shifts
1H
dimethylsulfoxided6
Chemical shifts
1H
CDCl3 dimethylsulfoxided6
Temperature (NMR Spectroscopy)
Frequency (NMR Spectroscopy) 300 MHz
Reference Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details De Boer; Tan; Gorter; Van de Wal; Kettenes-van den Bosch; De Bruijn; Maes
Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 - 1246 Title/Abstract Full Text View citing articles Show Details
1 °C
IR Spectroscopy (1) Description (IR Spectroscopy)
Solvent (IR Spectroscopy)
Reference
Bands
KBr
Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (5) 1 of 5
2 of 5
3 of 5
Comment (Pharmacological Data)
Bioactivities present
Reference
Braun; Shulgin
Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details
De Boer; Tan; Gorter; Van de Wal; Kettenes-van den Bosch; De Bruijn; Maes
Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 - 1246 Title/Abstract Full Text View citing articles Show Details
Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
transport; inhibition of
Species or TestSystem (Pharmacological Data)
rat phaeochromocytoma PC12 cells
Concentration (Pharmacological Data)
1E-08 - 0.0005 mol/l
Method (Pharmacological Data)
cells expressed NET, at 80percent confluency; incubation with 10 μmol/l <3H>noradrenaline and title comp. in HEPES buffer for 5 min at 37 deg C; radioactivity incorporated in cells was determined by liquid scintillation spectroscopy
Further Details (Pharmacological Data)
nonspecific <3H>noradrenaline uptake was determined in presence of nisoxetine; reference comp.: 3,4-methylenedioxymethamphetamine (inhibition conc. 50 = 6.6 μmol/l); NET: noradrenaline transporter
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
87.8 μmol/l
Results
title comp. inhibited NET-mediated <3H>noradrenaline uptake in competitive manner
Reference
Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
transport; inhibition of
Species or TestSystem (Pharmacological Data)
rat phaeochromocytoma PC12 cells
Concentration (Pharmacological Data)
1E-08 - 0.0005 mol/l
Method (Pharmacological Data)
cells expressed NET, at 80percent confluency; incubation with 10 μmol/l <3H>noradrenaline and title comp. in HEPES buffer for 5 min at 37 deg C; radioactivity incorporated in cells was determined by liquid scintillation spectroscopy
Further Details (Pharmacological Data)
nonspecific <3H>noradrenaline uptake was determined in presence of nisoxetine; reference comp.: 3,4-methylenedioxymethamphetamine (Ki = 0.6 μmol/l); NET: noradrenaline transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
6.3 μmol/l
Results
title comp. inhibited NET-mediated <3H>noradrenaline uptake in competitive manner
Reference
Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details
4 of 5
5 of 5
Effect (Pharmacological Data)
transport; inhibition of
Species or TestSystem (Pharmacological Data)
T-REx SERT HEK293 cells
Concentration (Pharmacological Data)
1E-08 - 0.0005 mol/l
Method (Pharmacological Data)
cells at 80percent confluency; incubation with 10 μmol/l <3H>5-hydroxytryptamine and title comp. for 6 min at 37 deg C; radioactivity incorporated in cells was determined by liquid scintillation spectroscopy
Further Details (Pharmacological Data)
nonspecific <3H>5-hydroxytryptamine uptake was determined in presence of paroxetine; reference comp.: 3,4methylenedioxymethamphetamine (inhibition conc. 50 = 34.8 μmol/l); SERT: 5-hydroxytryptamine transporter
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
215.3 μmol/l
Results
title comp. inhibited SERT-mediated <3H>5-hydroxytryptamine uptake in competitive manner
Reference
Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
transport; inhibition of
Species or TestSystem (Pharmacological Data)
T-REx SERT HEK293 cells
Concentration (Pharmacological Data)
1E-08 - 0.0005 mol/l
Method (Pharmacological Data)
cells at 80percent confluency; incubation with 10 μmol/l <3H>5-hydroxytryptamine and title comp. for 6 min at 37 deg C; radioactivity incorporated in cells was determined by liquid scintillation spectroscopy
Further Details (Pharmacological Data)
nonspecific <3H>5-hydroxytryptamine uptake was determined in presence of paroxetine; reference comp.: 3,4methylenedioxymethamphetamine (inhibition conc. 50 = 2.5 μmol/l); SERT: 5-hydroxytryptamine transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
15.4 μmol/l
Results
title comp. inhibited SERT-mediated <3H>5-hydroxytryptamine uptake in competitive manner
Reference
Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details
Reaxys Registry Number: 25077278
Molecular Formula: C10H13NO3
Linear Structure Formula: C10H13NO3
Molecular Weight: 195.218 InChI Key: FNDCTJYFKOQGTL-ZETCQYMHSA-N
3
no reactions.
Bioactivity (1)
1
Synthesize | Hide Details Find similar
Bioactivity Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Reference
Montgomery; Buon; Eibauer; Guiry; Keenan; McBean
British Journal of Pharmacology, 2007 , vol. 152, # 7 p. 1121 - 1130 Title/Abstract Full Text View citing articles Show Details