2-Aminoindane
Chemical compound
From Wikipedia, the free encyclopedia
2-Aminoindane (2-AI) is a stimulant of the 2-aminoindane family which has been sold as a designer drug.[2]
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| Other names | 2-Indanylamine; 2-Indanamine, SU-8629.[1] |
| Routes of administration | Oral |
| Drug class | Norepinephrine–dopamine releasing agent; Stimulant |
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| ECHA InfoCard | 100.019.111 |
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| Formula | C9H11N |
| Molar mass | 133.194 g·mol−1 |
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Pharmacology
Pharmacodynamics
2-AI is a monoamine releasing agent acting as a selective substrate for NET and DAT.[3][4] It partially substitutes for amphetamine in rodent drug discrimination tests.[5][6]
| Compound | Monoamine release (EC50, nM) | Ref | ||
|---|---|---|---|---|
| Serotonin | Norepinephrine | Dopamine | ||
| 2-AI | >10,000 | 86 | 439 | [7] |
| MDAI | 114 | 117 | 1,334 | [7] |
| MMAI | 31 | 3,101 | >10,000 | [7] |
| MEAI | 134 | 861 | 2,646 | [7] |
| d-Amphetamine | 698–1,765 | 6.6–7.2 | 5.8–24.8 | [8][9][10][11][12] |
| MDA | 160–162 | 47–108 | 106–190 | [13][10][14] |
| MDMA | 50–85 | 54–110 | 51–278 | [8][15][16][13][14] |
| 3-MA | ND | 58.0 | 103 | [10] |
| Notes: The smaller the value, the more strongly the compound produces the effect. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [7] | ||||
Chemistry
Synthesis
The chemical synthesis of 2-aminoindane was reported. For example, a 79% yield was reported from indene and ammonia precursors.[17] The older method uses 1-indanone as the starting material.[18]
Analogues
2-AI is a rigid analogue of amphetamine and has similar effects in rodents.[5][6] Other related homologues and rigid analogues of amphetamine include 2-aminotetralin (2-AT), 2-amino-1,2-dihydronapthalene (2-ADN), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 1-phenylpiperazine (1-PP), 6-AB, and 7-AB.[6][5][19]
Derivatives
A number of derivatives of 2-aminoindane, also known as substituted 2-aminoindanes, are known, including 5-IAI, aprindine, BFAI, BFMAI, DHAI, DOM-AI[20][21] ETAI, indantadol, MDAI, MEAI (5-MeO-2-AI), MDMAI, MMAI, NM-2-AI, PNU-99,194, Pyr-AI, and TAI, among others. Rexaceract (c.f. GT-02287) contains the 2-AI pharmacophore.
Society and culture
Legal status
China
As of October 2015 2-AI is a controlled substance in China.[22]
Finland
Scheduled in the "Government decree on psychoactive substances banned from the consumer market".[23]
Sweden
Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.[24]
United States
2-Aminoindane is not scheduled at the federal level in the United States,[25] but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.