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2-Aminoindane

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2-Aminoindane
Structural formula of 2-aminoindane
Ball-and-stick model of the 2-aminoindane molecule
Clinical data
Other names2-Indanylamine; 2-Indanamine
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 2,3-Dihydro-1H-inden-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.019.111 Edit this at Wikidata
Chemical and physical data
FormulaC9H11N
Molar mass133.194 g·mol−1
3D model (JSmol)
  • C1C(CC2=CC=CC=C21)N
  • InChI=1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2 checkY
  • Key:LMHHFZAXSANGGM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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

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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 drug discrimination tests.[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-ABTooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.[6][5][7]

Chemical derivatives

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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

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Activities of selected 2-aminoindanes[8]
Compound Monoamine release (EC50Tooltip half-maximal effective concentration, 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.
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China

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As of October 2015 2-AI is a controlled substance in China.[9]

Sweden

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Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.[10]

United States

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2-Aminoindane is not scheduled at the federal level in the United States,[11] but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

References

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  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. 12 (1): 145–151. 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. ^ a b 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.
  6. ^ a b Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav. 21 (6): 895–901. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418.
  7. ^ Hathaway BA, Nichols DE, Nichols MB, Yim GK (May 1982). "A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene". Journal of Medicinal Chemistry. 25 (5): 535–538. doi:10.1021/jm00347a011. PMID 6123601.
  8. ^ 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.
  9. ^ "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.
  10. ^ "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.
  11. ^ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2018-02-14.
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