Jump to content
 







Main menu
   


Navigation  



Main page
Contents
Current events
Random article
About Wikipedia
Contact us
Donate
 




Contribute  



Help
Learn to edit
Community portal
Recent changes
Upload file
 








Search  

































Create account

Log in
 









Create account
 Log in
 




Pages for logged out editors learn more  



Contributions
Talk
 



















Contents

   



(Top)
 


1 Chemistry  





2 References  














MDMAI






Српски / srpski
Srpskohrvatski / српскохрватски
 

Edit links
 









Article
Talk
 

















Read
Edit
View history
 








Tools
   


Actions  



Read
Edit
View history
 




General  



What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Cite this page
Get shortened URL
Download QR code
Wikidata item
 




Print/export  



Download as PDF
Printable version
 
















Appearance
   

 






From Wikipedia, the free encyclopedia
 


5,6-Methylenedioxy-N-methyl-2-aminoindane
Structural formula of MDMAI
Ball-and-stick model of the MDMAI molecule
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
  • Identifiers
    • N-methyl-6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine

    CAS Number
    PubChem CID
    ChemSpider
    UNII
    CompTox Dashboard (EPA)
    Chemical and physical data
    FormulaC11H13NO2
    Molar mass191.230 g·mol−1
    3D model (JSmol)
    • C3c2cc1OCOc1cc2CC3NC

    • InChI=1S/C11H13NO2/c1-12-9-2-7-4-10-11(14-6-13-10)5-8(7)3-9/h4-5,9,12H,2-3,6H2,1H3 checkY

    • Key:KNZKMFXEUONVMF-UHFFFAOYSA-N checkY

     ☒NcheckY (what is this?)  (verify)

    5,6-Methylenedioxy-N-methyl-2-aminoindane (MDMAI), is a drug developed in the 1990s by a team led by David E. NicholsatPurdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in animals and a putative entactogen in humans.[1]

    Chemistry

    [edit]

    MDMAI can be thought of as a cyclised analogueofMDMA where the alpha-methyl carbon of the alkylamino side chain has been joined back round to the 6-position of the aromatic ring to form an indane ring system. This changes the core structure of the molecule from phenethylaminetoaminoindane, and causes the pharmacological properties of the two compounds to be substantially different.[1]

    References

    [edit]
    1. ^ a b Oberlender R, Nichols DE (1990). "(+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity". J Pharmacol Exp Ther. 255 (3): 1098–1106. PMID 1979813.

    Retrieved from "https://en.wikipedia.org/w/index.php?title=MDMAI&oldid=1120100233"

    Categories: 
    Drugs not assigned an ATC code
    Entactogens and empathogens
    Designer drugs
    Benzodioxoles
    Serotonin releasing agents
    Hidden categories: 
    Articles with short description
    Short description matches Wikidata
    Articles needing additional references from October 2014
    All articles needing additional references
    Articles with changed CASNo identifier
    Infobox drug articles with non-default infobox title
    Articles without EBI source
    Chemical pages without DrugBank identifier
    Articles without KEGG source
    Drugboxes which contain changes to verified fields
     



    This page was last edited on 5 November 2022, at 04:24 (UTC).

    Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Mobile view



    Wikimedia Foundation
    Powered by MediaWiki