2-Aminoindane

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]

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
  • 2,3-Dihydro-1H-inden-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.019.111
Chemical and physical data
FormulaC9H11N
Molar mass133.194 g·mol−1
3D model (JSmol)
  • C1C(CC2=CC=CC=C21)N
  • InChI=1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2 checkY
  • Key:LMHHFZAXSANGGM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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:

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. Manier SK, Felske C, Eckstein N, Meyer MR (October 2019). "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. doi:10.1002/dta.2699. PMID 31667988.
  2. Halberstadt AL, Brandt SD, Walther D, Baumann MH (March 2019). "2-adrenergic receptors". Psychopharmacology. 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940.
  3. Simmler LD, Rickli A, Schramm Y, Hoener MC, Liechti ME (March 2014). "Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives" (PDF). Biochemical Pharmacology. 88 (2): 237–44. doi:10.1016/j.bcp.2014.01.024. PMID 24486525.
  4. Pinterova N, Horsley RR, Palenicek T (2017). "Synthetic Aminoindanes: A Summary of Existing Knowledge". Frontiers in Psychiatry. 8: 236. doi:10.3389/fpsyt.2017.00236. PMC 5698283. PMID 29204127.
  5. Oberlender R, Nichols DE (March 1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior. 38 (3): 581–6. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. S2CID 19069907.
  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" [On the issuance of non-pharmaceutical narcotic drugs and psychotropic substances listed in the notice] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  7. "Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara" [Eight substances are proposed to be classified as narcotics or dangerous to health] (in Swedish). Folkhälsomyndigheten. 24 June 2019.
  8. "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2018-02-14.
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