2-Aminoindane

Last updated
2-Aminoindane
2-Aminoindane.svg
2-Aminoindane 3D ball.png
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 InfoCard 100.019.111 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H11N
Molar mass 133.194 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 Yes check.svgY
  • Key:LMHHFZAXSANGGM-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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 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-AB Tooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-AB Tooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene. [6] [5] [7]

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

Pharmacodynamics

Activities of 2-aminoindanes and amphetamine relatives
Compound Monoamine release (EC50 Tooltip half-maximal effective concentration, nM)Ref
Serotonin Norepinephrine Dopamine
2-AI >10,00086439 [8]
MDAI 1141171,334 [8]
MMAI 313,101>10,000 [8]
MEAI 1348612,646 [8]
d-Amphetamine 698–1,7656.6–7.25.8–24.8 [9] [10] [11] [12] [13]
MDA 160–16247–108106–190 [14] [11] [15]
MDMA 50–8554–11051–278 [9] [16] [17] [14] [15]
3-MA ND58.0103 [11]
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: [8]

Society and culture

China

As of October 2015 2-AI is a controlled substance in China. [18]

Finland

Scheduled in the "Government decree on psychoactive substances banned from the consumer market". [19]

Sweden

Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019. [20]

United States

2-Aminoindane is not scheduled at the federal level in the United States, [21] but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

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. 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. 1 2 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. 1 2 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. 1 2 3 4 5 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. 1 2 Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse. 39 (1): 32–41. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID   11071707. S2CID   15573624.
  10. ↑ Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW (March 2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology. 38 (4): 552–562. doi:10.1038/npp.2012.204. PMC   3572453 . PMID   23072836.
  11. 1 2 3 Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN   978-0-470-11790-3. OCLC   181862653. OL   18589888W.
  12. ↑ Glennon RA, Dukat M (2017). "Structure-Activity Relationships of Synthetic Cathinones". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. pp. 19–47. doi:10.1007/7854_2016_41. ISBN   978-3-319-52442-9. PMC   5818155 . PMID   27830576.
  13. ↑ Partilla JS, Dersch CM, Baumann MH, Carroll FI, Rothman RB (1999). "Profiling CNS Stimulants with a High-Throughput Assay for Biogenic Amine Transporter Substractes". Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc (PDF). NIDA Res Monogr. Vol. 180. pp. 1–476 (252). PMID   11680410. RESULTS. Methamphetamine and amphetamine potently released NE (IC50s = 14.3 and 7.0 nM) and DA (IC50s = 40.4 nM and 24.8 nM), and were much less potent releasers of 5-HT (IC50s = 740 nM and 1765 nM). [...]
  14. 1 2 Setola V, Hufeisen SJ, Grande-Allen KJ, Vesely I, Glennon RA, Blough B, Rothman RB, Roth BL (June 2003). "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Molecular Pharmacology. 63 (6): 1223–1229. doi:10.1124/mol.63.6.1223. PMID   12761331. S2CID   839426.
  15. 1 2 Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH (December 2020). "The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats". Psychopharmacology (Berl). 237 (12): 3703–3714. doi:10.1007/s00213-020-05648-z. PMC   7686291 . PMID   32875347.
  16. ↑ Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV (April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology. 37 (5): 1192–1203. doi:10.1038/npp.2011.304. PMC   3306880 . PMID   22169943.
  17. ↑ Marusich JA, Antonazzo KR, Blough BE, Brandt SD, Kavanagh PV, Partilla JS, Baumann MH (February 2016). "The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue". Neuropharmacology. 101: 68–75. doi:10.1016/j.neuropharm.2015.09.004. PMC   4681602 . PMID   26362361.
  18. ↑ "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.
  19. ↑ "FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014".
  20. ↑ "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. ↑ "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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