2-Aminoindane
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| Clinical data | |
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| Other names | 2-Indanylamine; 2-Indanamine |
| Routes of administration | Oral |
| ATC code |
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| Legal status | |
| Legal status |
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| Identifiers | |
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| CAS Number | |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.019.111 |
| Chemical and physical data | |
| Formula | C9H11N |
| Molar mass | 133.194 g·mol−1 |
| 3D model (JSmol) | |
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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
[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. 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
[edit]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
[edit]| Compound | Monoamine release (EC50, nM) | ||
|---|---|---|---|
| Serotonin | Norepinephrine | Dopamine | |
| 2-AI | >10000 | 86 | 439 |
| MDAI | 114 | 117 | 1334 |
| MMAI | 31 | 3101 | >10000 |
| MEAI | 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
[edit]China
[edit]As of October 2015 2-AI is a controlled substance in China.[7]
Sweden
[edit]Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.[8]
United States
[edit]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.
See also
[edit]- 2-Aminodilin (2-AD)
- 2-Aminotetralin (2-AT)
- Amphetamine
- Bath salts (drug)
References
[edit]- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Halberstadt AL, Brandt SD, Walther D, Baumann MH (March 2019). "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940.
- ^ "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.
- ^ "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.
- ^ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2018-02-14.
External links
[edit]
Media related to 2-Aminoindane at Wikimedia Commons
