2-Aminoindane

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2-Aminoindane
Structural formula of 2-aminoindane
Ball-and-stick model of the 2-aminoindane molecule
Clinical data
Synonyms2-indanylamine;
2-indanamine
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.019.111 Edit this at Wikidata
Chemical and physical data
FormulaC9H11N
Molar mass133.190 g/mol g·mol−1
3D model (JSmol)
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2-Aminoindane (2-AI) is a research chemical and drug with applications in neurologic disorders and psychotherapy. It is also a drug of abuse as a component of some bath salts, with potential for neurotoxicity and brain damage.

Therapeutic and illicit uses[edit]

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. They are also commonly abused in the form of bath salts and widely substituted for ecstacy. Having a serotonergic mechanism, there is concern about risk for serotonin syndrome with their abuse. Deaths related to their toxic effects have been observed both in the laboratory in animal studies and in clinical encounters.[1] 2-AI is a rigid analogue of amphetamine and partially substitutes for it in rat discrimination tests.[2]

Chemical derivatives[edit]

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

Legality[edit]

China[edit]

As of October 2015 2-AI is a controlled substance in China.[3]

United States[edit]

2-Aminoindane is not scheduled at the federal level in the United States,[4] 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[edit]

References[edit]

  1. ^ 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.
  2. ^ Oberlender R, Nichols DE. (1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacol Biochem Behav. 38 (3): 581–586. doi:10.1016/0091-3057(91)90017-V. PMID 2068194.
  3. ^ "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. Retrieved 1 October 2015.
  4. ^ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.