Chemical compound
Pharmaceutical compound
2-Aminoindane (2-AI ) is anaminoindane andresearch chemical with applications in neurologic disorders and psychotherapy that has also been sold as adesigner drug .[ 1] NET andDAT .[ 2] [ 3]
Therapeutic and illicit uses [ edit ] Synthetic aminoindanes were originally developed in the context ofanti-Parkinsonian drugs as a metabolite ofrasagiline and as a tool to be used inpsychotherapy . 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 rigidanalogue ofamphetamine and partially substitutes for it inrat drug discrimination tests.[ 5] [ 6] 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 , and7-AB Tooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene .[ 6] [ 5] [ 7]
Chemical derivatives [ edit ] There are a number of notablederivatives of 2-aminoindane that exist, including:
A number of notable derivatives of1-aminoindan , apositional isomer of 2-aminoindan, also exist, such asrasagiline andladostigil , among others.
Jimscaline ,2CB-Ind , andAMMI are derivatives of1-aminomethylindane , anindane - andamine -containingcompound related to 1-aminoindan.
Society and culture [ edit ] As of October 2015 2-AI is a controlled substance in China.[ 20]
Scheduled in the "Government decree on psychoactive substances banned from the consumer market".[ 21]
Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.[ 22]
2-Aminoindane is not scheduled at the federal level in theUnited States ,[ 23] Federal Analog Act .
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"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 . ^ 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 . ^ Nichols DE, Weintraub HJ, Pfister WR, Yim GK (1978)."The Use of Rigid Analogues to Probe Hallucinogen Receptors" .QuaSAR, Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens 70– 83. ^ Nichols DE, Barfknecht CF, Long JP, Standridge RT, Howell HG, Partyka RA, Dyer DC (February 1974). "Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)".J Med Chem .17 (2):161– 166.doi :10.1021/jm00248a004 .PMID 4809251 . ^a b c d e 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 . ^a b 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 . ^ 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 . ^a b c Blough B (July 2008)."Dopamine-releasing agents" (PDF) . In Trudell ML, Izenwasser S (eds.).Dopamine Transporters: Chemistry, Biology and Pharmacology 305– 320.ISBN 978-0-470-11790-3 OCLC 181862653 .OL 18589888W . ^ 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 . ^ 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). [...] ^a b 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 . ^a b 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 . ^ 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 . ^ 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 . ^ "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 fromthe original on 1 October 2015. Retrieved1 October 2015 .^ "FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014" .^ "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 fromthe original on 2009-08-27. Retrieved2018-02-14 .
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