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

Clinical data
Other names	2-indanylamine; 2-indanamine
Routes of administration	Oral
ATC code	none
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act In general: uncontrolled
Identifiers
IUPAC name 2,3-Dihydro-1H-inden-2-amine
CAS Number	2975-41-9^N
PubChem CID	76310
ChemSpider	68787^Y
UNII	1P810SQ3EY
CompTox Dashboard (EPA)	DTXSID40183902
ECHA InfoCard	100.019.111
Chemical and physical data
Formula	C9H11N
Molar mass	133.194 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C1C(CC2=CC=CC=C21)N
InChI InChI=1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2^Y Key:LMHHFZAXSANGGM-UHFFFAOYSA-N^Y
^NY (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]

Legal status

Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.[6]

Chemical derivatives

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

• 5-IAI
• Aprindine
• ETAI
• Indanorex
• Indantadol
• Jimscaline
• Ladostigil
• MDAI
• MDMAI
• MMAI
• NM-2-AI
• PNU-99,194
• Rasagiline
• TAI

Legality

China

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

• 2-Aminodilin (2-AD)
• 2-Aminotetralin (2-AT)
• Amphetamine
• Bath salts (drug)

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. 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.
6. "Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 24 June 2019.
7. "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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
8. 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.