2-Aminoindane Explained

2-Aminoindane (2-AI) is an aminoindane and 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 notable derivatives of 2-aminoindane that exist, including:

A number of notable derivatives of 1-aminoindan, a positional isomer of 2-aminoindan, also exist, such as rasagiline and ladostigil, among others.

Jimscaline, 2CB-Ind, and AMMI are derivatives of 1-aminomethylindane, an indane- and amine-containing compound related to 1-aminoindan.

Pharmacology

Activities of selected 2-aminoindanes^[6]
Compound	Monoamine release (nM)
Compound			Dopamine
	>10000	86	439
	114	117	1334
	31	3101	>10000
	134	861	2646
Notes: The smaller the value, the more strongly the compound produces the effect. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds.

Legal status

China

As of October 2015 2-AI is a controlled substance in China.^[7]

Sweden

Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.^[8]

United States

2-Aminoindane is not scheduled at the federal level in the United States,^[9] but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

Notes and References

Manier SK, Felske C, Eckstein N, Meyer MR . 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 . October 2019 . 12 . 1 . 145–151 . 31667988 . 10.1002/dta.2699 . free .
Halberstadt AL, Brandt SD, Walther D, Baumann MH . 2-adrenergic receptors . Psychopharmacology . 236 . 3 . 989–999 . March 2019 . 30904940 . 6848746 . 10.1007/s00213-019-05207-1 .
Simmler LD, Rickli A, Schramm Y, Hoener MC, Liechti ME . Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives . Biochemical Pharmacology . 88 . 2 . 237–44 . March 2014 . 24486525 . 10.1016/j.bcp.2014.01.024 .
Pinterova N, Horsley RR, Palenicek T . Synthetic Aminoindanes: A Summary of Existing Knowledge . Frontiers in Psychiatry . 8 . 236 . 2017 . 29204127 . 5698283 . 10.3389/fpsyt.2017.00236 . free .
Oberlender R, Nichols DE . Structural variation and (+)-amphetamine-like discriminative stimulus properties . Pharmacology, Biochemistry, and Behavior . 38 . 3 . 581–6 . March 1991 . 2068194 . 10.1016/0091-3057(91)90017-V . 19069907 .
Halberstadt AL, Brandt SD, Walther D, Baumann MH . 2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors . Psychopharmacology (Berl) . 236 . 3 . 989–999 . March 2019 . 30904940 . 6848746 . 10.1007/s00213-019-05207-1 .
Web site: 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. China Food and Drug Administration . 27 September 2015 . Chinese . 1 October 2015 . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . 1 October 2015 . dead .
Web site: Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara . Eight substances are proposed to be classified as narcotics or dangerous to health. Folkhälsomyndigheten . sv . 24 June 2019 .
Web site: 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. . 2018-02-14 . 2009-08-27 . https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm . dead .