Chemistry:2-Aminoindane

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2-Aminoindane (2-AI) is a stimulant of the 2-aminoindane family which has been sold as a designer drug.[1]

Pharmacology

Pharmacodynamics

2-AI is a monoamine releasing agent acting as a selective substrate for NET and DAT.[2][3] It partially substitutes for amphetamine in rodent drug discrimination tests.[4][5]

Activities of 2-aminoindanes and amphetamine relatives
Compound Monoamine release (EC50, nM) Ref
Serotonin Norepinephrine Dopamine
2-AI >10,000 86 439 [6]
MDAI 114 117 1,334 [6]
MMAI 31 3,101 >10,000 [6]
MEAI 134 861 2,646 [6]
d-Amphetamine 698–1,765 6.6–7.2 5.8–24.8 [7][8][9][10][11]
MDA 160–162 47–108 106–190 [12][9][13]
MDMA 50–85 54–110 51–278 [7][14][15][12][13]
3-MA ND 58.0 103 [9]
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: [6]

Chemistry

Synthesis

The chemical synthesis of 2-aminoindane was reported. For example, a 79% yield was reported from indene and ammonia precursors.[16] The older method uses 1-indanone as the starting material.[17]

Analogues

2-AI is a rigid analogue of amphetamine and has similar effects in rodents.[4][5] 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.[5][4][18]

Derivatives

Main article: Chemistry:Substituted 2-aminoindane

A number of derivatives of 2-aminoindane, also known as substituted 2-aminoindanes, are known, including 5-IAI, aprindine, BFAI, BFMAI, DHAI, DOM-AI[19][20] 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

China

As of October 2015 2-AI is a controlled substance in China.[21]

Finland

Scheduled in the "Government decree on psychoactive substances banned from the consumer market".[22]

Sweden

Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.[23]

United States

2-Aminoindane is not scheduled at the federal level in the United States,[24] 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

References

  1. ↑ "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. October 2019. doi:10.1002/dta.2699. PMID 31667988. 
  2. ↑ "2-adrenergic receptors". Psychopharmacology 236 (3): 989–999. March 2019. doi:10.1007/s00213-019-05207-1. PMID 30904940. 
  3. ↑ "Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives". Biochemical Pharmacology 88 (2): 237–44. March 2014. doi:10.1016/j.bcp.2014.01.024. PMID 24486525. http://edoc.unibas.ch/56166/1/20170921163100_59c3cd2473bad.pdf. 
  4. ↑ 4.0 4.1 4.2 "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior 38 (3): 581–6. March 1991. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=77437efa02b4a0f688e4038b153ddfafde6da614. 
  5. ↑ 5.0 5.1 5.2 "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav 21 (6): 895–901. December 1984. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418. 
  6. ↑ 6.0 6.1 6.2 6.3 6.4 "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. doi:10.1007/s00213-019-05207-1. PMID 30904940. 
  7. ↑ 7.0 7.1 "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse 39 (1): 32–41. January 2001. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707. 
  8. ↑ "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology 38 (4): 552–562. March 2013. doi:10.1038/npp.2012.204. PMID 23072836. 
  9. ↑ 9.0 9.1 9.2 "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. July 2008. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf. 
  10. ↑ "Structure-Activity Relationships of Synthetic Cathinones". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. 32. 2017. pp. 19–47. doi:10.1007/7854_2016_41. ISBN 978-3-319-52442-9. 
  11. ↑ "Profiling CNS Stimulants with a High-Throughput Assay for Biogenic Amine Transporter Substrates". Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc. NIDA Res Monogr. 180. 1999. pp. 1–476 (252). https://archives.nida.nih.gov/sites/default/files/180.pdf#page=261. "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). [...]" 
  12. ↑ 12.0 12.1 "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Molecular Pharmacology 63 (6): 1223–1229. June 2003. doi:10.1124/mol.63.6.1223. PMID 12761331. 
  13. ↑ 13.0 13.1 "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. December 2020. doi:10.1007/s00213-020-05648-z. PMID 32875347. 
  14. ↑ "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology 37 (5): 1192–1203. April 2012. doi:10.1038/npp.2011.304. PMID 22169943. 
  15. ↑ "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. February 2016. doi:10.1016/j.neuropharm.2015.09.004. PMID 26362361. 
  16. ↑ "Redox-Photosensitized Aminations of 1,2-Benzo-1,3-cycloalkadienes, Arylcyclopropanes, and Quadricyclane with Ammonia". The Journal of Organic Chemistry 68 (20): 7618–7624. 1 October 2003. doi:10.1021/jo030053+. https://pubs.acs.org/doi/10.1021/jo030053%2B. 
  17. ↑ "PHYSIOLOGICALLY ACTIVE INDANAMINES 1". The Journal of Organic Chemistry 09 (4): 380–391. July 1944. doi:10.1021/jo01186a010. https://pubs.acs.org/doi/abs/10.1021/jo01186a010. 
  18. ↑ "A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene". Journal of Medicinal Chemistry 25 (5): 535–538. May 1982. doi:10.1021/jm00347a011. PMID 6123601. 
  19. ↑ "The Use of Rigid Analogues to Probe Hallucinogen Receptors". QuaSAR, Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. Department of Health, Education, and Welfare, Public Health Service, Alcohol, Drug Abuse, and Mental Health Administration. 1978. pp. 70–83. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=7ec3b34f01bca1140244abd0c87473cf38701e50#page=81. 
  20. ↑ "Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)". J Med Chem 17 (2): 161–166. February 1974. doi:10.1021/jm00248a004. PMID 4809251. 
  21. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  22. ↑ "FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014". https://finlex.fi/fi/lainsaadanto/2014/1130. 
  23. ↑ "Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 24 June 2019. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/juni/atta-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/. 
  24. ↑ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.". http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm. 



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