Query Query H 2N
Results
Date
3 substances in Reaxys
2017-10-22 19h:33m:33s (EST)
O
1. Query
O O
Search as: As drawn
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2017-10-22 19:40:14
Reaxys ID 1246630 View in Reaxys
H 2N
1/3 CAS Registry Number: 13674-05-0 Chemical Name: MMDA; 3-methoxy-4,5-methylenedioxyamphetamine; 2-(7-methoxy-benzo[1,3]dioxol-5-yl)-1-methyl-ethylamine; 3-methoxy-4,5-methylenedioxyphenylisopropylamine; (d,l)-3-methoxy-4,5-methylenedioxyamphetamine; 3-Methoxy-4,5-methylenedioxyamphetamine; 3-methoxy-4, 5 methylenedioxyamphetamine Linear Structure Formula: C11H15NO3 Molecular Formula: C11H15NO3 Molecular Weight: 209.245 Type of Substance: heterocyclic InChI Key: YQYUWUKDEVZFDB-UHFFFAOYSA-N Note:
O O O
Substance Label (5) Label References 3
Patent; DADE BEHRING INC.; WO2005/61482; (2005); (A1) English, View in Reaxys
14 (Tab.I)
Barfknecht et al.; Journal of Medicinal Chemistry; vol. 18; (1975); p. 208,209, View in Reaxys
14 Tab. I
Barfknecht et al.; Journal of Medicinal Chemistry; vol. 18; (1975); p. 208,209, View in Reaxys
Verb. No. 14 (Table I)
Barfknecht et al.; Journal of Medicinal Chemistry; vol. 18; (1975); p. 208,209, View in Reaxys
II, MMDA
Shulgin; Experientia; vol. 20; nb. 7; (1964); p. 366 - 367, View in Reaxys
Patent-Specific Data (3) Prophetic ComLocation in Patent References pound prophetic product
Patent; Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.; US2007/27208; (2007); (A1) English, View in Reaxys Patent; DADE BEHRING INC.; WO2005/61482; (2005); (A1) English, View in Reaxys Claim
Patent; Ekins, Sean; US2002/13372; (2002); (A1) English, View in Reaxys
Druglikeness (1) 1 of 1
LogP
1.166
H Bond Donors
1
H Bond Acceptors
1
Rotatable Bonds
3
TPSA
53.71
Lipinski Number
4
Veber Number
2
Derivative (1) Comment (Derivative) Hydrochlorid: F: 191grad
References Shulgin; Experientia; vol. 20; nb. 7; (1964); p. 366 - 367, 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 Medchem (15) 1 of 15
Substance Effect
Analgesic
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Substance RN
1246630View in Reaxys
Substance Name
MMDA
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Measurement Parameter
Qualitative
Qualitative value
@
; (2012); Type: Review, Lab: EFF_071212, Owner: EFFECT, Number: 000, Revision: 07.12.2012 00:00:00, View in Reaxys 2 of 15
Target Mutant/Chimera Details
Cytochrome P450 2D6 [human]:Wild
Target Species (Bioactivity)
human
Target Subunit Proteins
Cytochrome P450 2D6 [human]
Target Transfection
Non Transfected
Bioassay Category
Metabolism/Transport
Bioassay Name
Enzymology inhibition
Biological Species/NCBI Human ID Organs/Tissues
Liver
Cell Fraction
Microsome
Substance RN
1246630View in Reaxys
Substance Name
MMDA
Measurement Parameter
Ki
Unit
µM
Quantitative value
2.2
Measurement pX
5.66
Target, Subunit, Species Cytochrome P450 2D6 [human] Wu, Dafang; Victoria Otton, S.; Inaba, Tadanobu; Kalow, Werner; Sellers, Edward M.; Biochemical Pharmacology; vol. 53; nb. 11; (1997); p. 1605 - 1612, View in Reaxys
3 of 15
Target Subunit Synonyms
cyp2d6 (cytochrome p450 2d6); cyp2dl1; cypiid6; cytochrome p450 2d6; cytochrome p450-db1; debrisoquine 4-hydroxylase
Target Uniprot ID
p10635
Target PDB ID
2f9q; 3qm4; 3tbg; 3tda; 4wnt; 4wnu; 4wnv; 4wnw; 4xry; 4xrz
Metabolite RN (Data Point)
88093
Metabolite Name
Dextrorphan
Compound RN
88549; 24140787; 8137362; 3885115
Compound name
Dextromethorphan; Glucose-6-phosphate; KCl; NADP
Compound role
SUB; COM; SLV; COE
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Compound tested for hallucinogenic activity in humans was reported; Value reported in (A)= Mescaline units
Biological Species/NCBI Human ID Substance RN
1246630View in Reaxys
Measurement Parameter
Activity
Quantitative value
2
Clare, Brian W.; Journal of Medicinal Chemistry; vol. 41; nb. 20; (1998); p. 3845 - 3856, View in Reaxys
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4 of 15
Measurement Object
hallucinogenic activity
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Details
Lethal dose of compound in mice
Biological Species/NCBI Mus musculus ID Substance RN
1246630View in Reaxys
Measurement Parameter
LD50
Unit
mg/kg
Quantitative value
150
Shulgin; Experientia; vol. 20; nb. 7; (1964); p. 366 - 367, View in Reaxys 5 of 15
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Compound was tested for hallucinogenic potency in humans
Biological Species/NCBI Human ID Substance RN
1246630View in Reaxys
Measurement Parameter
Activity
Quantitative value
0.43
Barfknecht; Nichols; Dunn III; Journal of Medicinal Chemistry; vol. 18; nb. 2; (1975); p. 208 - 210, View in Reaxys
6 of 15
Measurement Object
log activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
log of hallucinogenic potency (A) of the compound was measured on humans
Biological Species/NCBI Human ID Substance RN
1246630View in Reaxys
Measurement Parameter
Qualitative
Altun, Ahmet; Golcuk, Kurtulus; Kumru, Mustafa; Jalbout, Abraham F.; Bioorganic and Medicinal Chemistry; vol. 11; nb. 18; (2003); p. 3861 - 3868, View in Reaxys
7 of 15
Measurement Object
log A
Bioassay Category
Metabolism/Transport
Bioassay Details
Hallucinogenic activity of the compound expressed as concentration required relative to mescaline
Substance RN
1246630View in Reaxys
Measurement Parameter
Qualitative
Kier; Hall; Journal of Medicinal Chemistry; vol. 20; nb. 12; (1977); p. 1631 - 1636, View in Reaxys
8 of 15
Measurement Object
log Mu
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Hallucinogenic potency (A) expressed as the ratio of the effective dose of mescaline to the effective dose of the compound measured on humans
Biological Species/NCBI Human ID Substance RN
1246630View in Reaxys
Measurement Parameter
Qualitative
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Altun, Ahmet; Golcuk, Kurtulus; Kumru, Mustafa; Jalbout, Abraham F.; Bioorganic and Medicinal Chemistry; vol. 11; nb. 18; (2003); p. 3861 - 3868, View in Reaxys
9 of 15
Measurement Object
potency
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Hallucinogenic activity of the compound was tested in human and expressed in terms of mescaline units (MU)
Biological Species/NCBI Human ID Substance RN
1246630View in Reaxys
Measurement Parameter
Qualitative
S.P.Gupta; Chemical reviews; vol. 89; nb. 8; (1989); p. 1765 - 1800, View in Reaxys
10 of 15
Measurement Object
MU
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Psychotomimetic activity of the compound expressed as mole mescaline to that of mole of the tested compound
Substance RN
1246630View in Reaxys
Measurement Parameter
Qualitative
Thakur, Mamta; Thakur, Abhilash; Khadikar, Padmakar V.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 4; (2004); p. 825 - 831, View in Reaxys
11 of 15
Measurement Object
log Mu
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Hallucinogenic activity of the compound was determined relative to mescaline in human; MU=activity in mescaline units
Biological Species/NCBI Human ID Substance RN
1246630View in Reaxys
Measurement Parameter
Qualitative
SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL; Chemical reviews; vol. 83; nb. 6; (1983); p. 633 - 649, View in Reaxys
12 of 15
Measurement Object
MU
Bioassay Category
Metabolism/Transport
Bioassay Details
Partition Coefficient of the compound was determined
Substance RN
1246630View in Reaxys
Measurement Parameter
Qualitative
Qualitative value
Not Published
S.P.Gupta; Chemical reviews; vol. 89; nb. 8; (1989); p. 1765 - 1800, View in Reaxys
13 of 15
Measurement Object
Partition coefficient
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Hallucinogenic activity measured as ratio of effective dose of mescaline to that of the compound in human
Biological Species/NCBI Human ID Substance RN
1246630View in Reaxys
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Measurement Parameter
Qualitative
Clare; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 687 - 702, View in Reaxys
14 of 15
Measurement Object
Activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effective dose of the compound in rats trained on 1 mg/kg DOM
Biological Species/NCBI Rattus norvegicus ID Substance RN
1246630View in Reaxys
Measurement Parameter
ED50
Unit
mg/kg
Qualitative value
=
Quantitative value
3.66
Clare; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 687 - 702, View in Reaxys 15 of 15
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Log value of hallucinogenic activity was determined
Biological Species/NCBI Human ID Substance RN
1246630View in Reaxys
Measurement Parameter
Activity
Quantitative value
0.431
Clare; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 687 - 702, View in Reaxys Measurement Object
log activity
Reaxys ID 11147871 View in Reaxys
2/3 Chemical Name: (+/-)-2-(7-[2H3]methoxy-benzo[1,3]dioxol-5yl)-1-methylethylamine Linear Structure Formula: C11H8NO3H4 (2)H3 Molecular Formula: C11H15NO3 Molecular Weight: 212.221 InChI Key: YQYUWUKDEVZFDB-BMSJAHLVSA-N Note:
H 2N O O 2H 2
H
O 2H
Substance Label (1) Label References 14
Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 7; (2007); p. 660 - 665, View in Reaxys
Druglikeness (1) 1 of 1
LogP
1.166
H Bond Donors
1
H Bond Acceptors
1
Rotatable Bonds
3
TPSA
53.71
Lipinski Number
4
Veber Number
2
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Melting Point (1) 1 of 1
Melting Point [°C]
190 - 191.5
Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 7; (2007); p. 660 - 665, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]
300
Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 7; (2007); p. 660 - 665, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]
75.5
Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 7; (2007); p. 660 - 665, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 7; (2007); p. 660 - 665, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)
Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 7; (2007); p. 660 - 665, View in Reaxys
Reaxys ID 9434202 View in Reaxys
Cl
3/3 Chemical Name: (d,l)-3-methoxy-4,5-methylenedioxyamphetamine Linear Structure Formula: C11H15NO3*ClH Molecular Formula: C11H15NO3*ClH Molecular Weight: 245.706 Type of Substance: heterocyclic InChI Key: HULCPMREEFWFRE-UHFFFAOYSA-N Note:
H
H 2N
O O O
Substance Label (1) Label References MMDA
Wu, Dafang; Victoria Otton, S.; Inaba, Tadanobu; Kalow, Werner; Sellers, Edward M.; Biochemical Pharmacology; vol. 53; nb. 11; (1997); p. 1605 - 1612, View in Reaxys
Druglikeness (1)
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1 of 1
LogP
1.678
H Bond Donors
1
H Bond Acceptors
1
Rotatable Bonds
3
TPSA
53.71
Lipinski Number
4
Veber Number
2
Medchem (1) 1 of 1
Bioassay Category
Metabolism/Transport
Bioassay Details
enzyme; inhib. ofhuman liver microsomesreaction started by adding microsomal protein; incubation at 37 deg C for 30 min; stopped with 70 percent perchloric acid; centrifuged; supernatant assayed for dextrorphan by HPLC
Biological Species/NCBI human ID Organs/Tissues
liver
Cell Fraction
Microsome
Substance RN
9434202View in Reaxys
Qualitative Results
competitive inhibitory effect; apparent inhibition constant (Ki) = 2.2 μmol/l
Measurement Parameter
Qualitative
Qualitative value
ND
Wu, Dafang; Victoria Otton, S.; Inaba, Tadanobu; Kalow, Werner; Sellers, Edward M.; Biochemical Pharmacology; vol. 53; nb. 11; (1997); p. 1605 - 1612, View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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