6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-6-amine [MDAI] [CAS 132741-81-2; InChIKey FQDRMHHCWZAXJM-UHF

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Results

Date

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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