Chemistry:2-Aminoindane

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Short description: Chemical compound
2-Aminoindane
Structural formula of 2-aminoindane
Ball-and-stick model of the 2-aminoindane molecule
Clinical data
Other names2-indanylamine;
2-indanamine
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC9H11N
Molar mass133.194 g·mol−1
3D model (JSmol)
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2-Aminoindane (2-AI) is a research chemical with applications in neurologic disorders and psychotherapy that has also been sold as a designer drug.[1] It acts as a selective substrate for NET and DAT.[2][3]

Therapeutic and illicit uses

Synthetic aminoindanes were originally developed in the context of anti-Parkinsonian drugs as a metabolite of rasagiline and as a tool to be used in psychotherapy. Deaths related to their toxic effects have been observed both in the laboratory in animal studies and in clinical encounters.[4] 2-AI is a rigid analogue of amphetamine and partially substitutes for it in rat discrimination tests.[5]

Chemical derivatives

There are a number of derivatives of 2-aminoindane and its positional isomer 1-aminoindane exist, including:


Legal status

China

As of October 2015 2-AI is a controlled substance in China.[6]

Sweden

Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.[7]

United States

2-Aminoindane is not scheduled at the federal level in the United States ,[8] but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

See also

References

  1. "The metabolic fate of two new psychoactive substances - 2-aminoindane and N-methyl-2-aminoindane - studied in vitro and in vivo to support drug testing". Drug Testing and Analysis 12 (1): 145–151. October 2019. doi:10.1002/dta.2699. PMID 31667988. 
  2. "2-adrenergic receptors". Psychopharmacology 236 (3): 989–999. March 2019. doi:10.1007/s00213-019-05207-1. PMID 30904940. 
  3. "Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives". Biochemical Pharmacology 88 (2): 237–44. March 2014. doi:10.1016/j.bcp.2014.01.024. PMID 24486525. http://edoc.unibas.ch/56166/1/20170921163100_59c3cd2473bad.pdf. 
  4. "Synthetic Aminoindanes: A Summary of Existing Knowledge". Frontiers in Psychiatry 8: 236. 2017. doi:10.3389/fpsyt.2017.00236. PMID 29204127. 
  5. "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior 38 (3): 581–6. March 1991. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. 
  6. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  7. "Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 24 June 2019. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/juni/atta-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/. 
  8. "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.". http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm. 

External links