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O
1. Query
2 substances in Re2016-02-22 07h:54m:16s (EST) axys
NH 2 O
Search as: As drawn
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Reaxys ID 3590651 View in Reaxys
1/2 CAS Registry Number: 132741-81-2 Chemical Name: 2-amino-5,6-(methylenedioxy)indane; 5,6(methylenedioxy)-2-aminoindan; 5,6-methylenedioxy-2-aminoindan Linear Structure Formula: C10H11NO2 Molecular Formula: C10H11NO2 Molecular Weight: 177.203 Type of Substance: heterocyclic InChI Key: FQDRMHHCWZAXJM-UHFFFAOYSA-N Note:
O NH 2 O
Substance Label (3) Label References 19
Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.; Medicinal Chemistry Research; vol. 6; nb. 6; (1996); p. 412 - 426, View in Reaxys
MDAI
Sprague, Jon E.; Johnson, Michael P.; Schmidt, Christopher J.; Nichols, David E.; Biochemical Pharmacology; vol. 52; nb. 8; (1996); p. 1271 - 1277, View in Reaxys
15b
Paleo, M. Rita; Dominguez, Domingo; Castedo, Luis; Tetrahedron; vol. 50; nb. 11; (1994); p. 3627 - 3638, View in Reaxys
Derivative (1) Derivative
References
5,6-(methyleneNichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M.; dioxy)-2-aminoin- Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys dan hydrochloride NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Nichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M.; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys 2 of 2
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)
1H-1H
Nichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M.; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys Pharmacological Data (5) 1 of 5
Comment (Pharmacological Data)
Bioactivities present
Nichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M.; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys; Paleo, M. Rita; Dominguez, Domingo; Castedo, Luis; Tetrahedron; vol. 50; nb. 11; (1994); p. 3627 - 3638, View in Reaxys; Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.; Medicinal Chemistry Research; vol. 6; nb. 6; (1996); p. 412 - 426, View in Reaxys; Sprague, Jon E.; Johnson, Michael P.; Schmidt, Christopher J.; Nichols, David E.; Biochemical Pharmacology; vol. 52; nb. 8; (1996); p. 1271 - 1277, View in Reaxys; Oberlender; Nichols; Journal of Pharmacology and Experimental Therapeutics; vol. 255; nb. 3; (1990); p. 1098 - 1106, View in Reaxys; Nichols; Brewster; Johnson; Oberlender; Riggs; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys 2 of 5
Effect (Pharmacological Data)
behavioural symptoms
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Species or Test-System (Pharmacological Data)
Sprague-Dawley rat
Sex
male
Route of Application
intraperitoneal
Concentration (Pharmacological Data)
0.3 - 0.75 mg/kg
Method (Pharmacological Data)
10 animals injected with 1.5 mg/kg of N-methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (ecstasy, MDMA) i.p., as training drug; title compound administered 15 min prior stimulus generalization recorded; extinction session 2.5 min
Further Details (Pharma- stimulus generalization: > 80 percent drug-appropriate responding cological Data) Type (Pharmacological Data)
ED50
Value of Type (Pharmacological Data)
0.56 mg/g
Results
produced 92 percent MDMA-appropriate responding at highest doses tested
Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.; Medicinal Chemistry Research; vol. 6; nb. 6; (1996); p. 412 - 426, View in Reaxys 3 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
human 5-HT2A receptors
Method (Pharmacological Data)
cells grown, harvested and competition assays performed using <3H>ketanserin or <3H>DOB radioligands
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
> 10000 nmol/l
Results
very low affinity both to <3H>ketanserin and <3H>DOB labeled receptors
Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.; Medicinal Chemistry Research; vol. 6; nb. 6; (1996); p. 412 - 426, View in Reaxys 4 of 5
Effect (Pharmacological Data)
central stimulation
Species or Test-System (Pharmacological Data)
albino ICR mice
Sex
male and female
Route of Application
intraperitoneal
Concentration (Pharmacological Data)
1 - 30 mg/kg
Kind of Dosing (Pharma- 1, 3, 10, and 30 mg/kg cological Data) Exposure Period (Pharmacological Data)
10 - 40 min
Method (Pharmacological Data)
mouse weight 25-30 g; acclimated for 30 min prior to drug treament; central stimulation assayed by locomotor activity (distance traversed) and by rearing frequency, recorded simultaneously by computerized video tracking and behavior recognition system
Results
weakly active both in locomotor activity and rearing frequency
Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.; Medicinal Chemistry Research; vol. 6; nb. 6; (1996); p. 412 - 426, View in Reaxys 5 of 5
Effect (Pharmacological Data)
drug interaction
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Species or Test-System (Pharmacological Data)
Sprague-Dawley rat
Sex
male
Route of Application
subcutaneous
Concentration (Pharmacological Data)
20 mg/kg
Method (Pharmacological Data)
in vivo; 24 rats (175-199 g) divided into 4 groups; 1. group injected i.p. 2.5 mg/kg clorgyline and 2. group i.p. injected 10 mg/kg L-deprenyl, 15 min after these treatments injected in both groups title comp., 3. group title comp. alone, 4. g. saline
Further Details (Pharma- effects of L-deprenyl and clorgyline on the neurochemical response to title comp.; 7 days cological Data) after treatments, the frontal cortex and striatum were removed and assayed for serotonin (5HT), 5-hydroxyindoleacetic acid and dopamine; HPLC/electrochem. detect. Results
both clorgyline and L-deprenyl failed to alter the neurochemical effects induced by title co. using 5-HT and 5-hydroxyacetic acid levels as markers; dopamine was increased signif. in the striatum by both clorgyline and L-deprenyl (47 and 38 percent), (diagram)
Sprague, Jon E.; Johnson, Michael P.; Schmidt, Christopher J.; Nichols, David E.; Biochemical Pharmacology; vol. 52; nb. 8; (1996); p. 1271 - 1277, View in Reaxys
Reaxys ID 3572813 View in Reaxys
O
2/2
Cl
CAS Registry Number: 124399-89-9 Chemical Name: 5,6-(methylenedioxy)-2-aminoindan hydrochloride Linear Structure Formula: C10H11NO2*ClH Molecular Formula: C10H11NO2*ClH Molecular Weight: 213.664 Type of Substance: heterocyclic InChI Key: DEZYWEZDXRXACY-UHFFFAOYSA-N Note:
H
NH 2 O
Substance Label (1) Label References 3a
Nichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M.; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
276
Nichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M.; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Nichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M.; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys; Nichols; Brewster; Johnson; Oberlender; Riggs; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys 2 of 2
Comment (Pharmacological Data)
Drug-discrimination data in MDMA- and LSD-trained rats; the effects on levels of monoamine and metabolite
Nichols, David E.; Brewster, William K.; Johnson, Michael P.; Oberlender, Robert; Riggs, Robert M.; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 703 - 710, View in Reaxys
Copyright © 2016 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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