2-Aminoindane

Chemical compound Substituted 2-aminoindane changed changed 477212458 2-Aminoindane structure.svg skin-invert-image Structural formula of 2-aminoindane 200px 2-Aminoindane 3D ball.png bg-transparent Ball-and-stick model of the 2-aminoindane molecule Oral Norepinephrine–dopamine releasing agent; Stimulant None NpSG PSA Uncontrolled changed ?? 2975-41-9 76310 correct chemspider 68787 1P810SQ3EY 2-Indanylamine; 2-Indanamine, SU-8629.PHARMACOLOGY OF 2-AMINO-INDANE HYDROCHLORIDE (SU-8629): A POTENT NON-NARCOTIC ANALGESIC. Witkin, L.B. et al. The Journal of Pharmacology and Experimental Therapeutics, Volume 133, Issue 3, 400 - 408 2,3-Dihydro-1H-inden-2-amine 9 11 1 C1C(CC2=CC=CC=C21)N correct chemspider 1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2 correct chemspider LMHHFZAXSANGGM-UHFFFAOYSA-N 2-Aminoindane (2-AI) is a stimulant of the 2-aminoindane family which has been sold as a designer drug. Manier SK, Felske C, Eckstein N, Meyer MR 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 October 2019 12 1 145–151 31667988 10.1002/dta.2699 free Pharmacology Pharmacodynamics 2-AI is a monoamine releasing agent acting as a selective substrate for NET and DAT. Halberstadt AL, Brandt SD, Walther D, Baumann MH 2-adrenergic receptors Psychopharmacology 236 3 989–999 March 2019 30904940 6848746 10.1007/s00213-019-05207-1 Simmler LD, Rickli A, Schramm Y, Hoener MC, Liechti ME Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives Biochemical Pharmacology 88 2 237–44 March 2014 24486525 10.1016/j.bcp.2014.01.024 http://edoc.unibas.ch/56166/1/20170921163100_59c3cd2473bad.pdf It partially substitutes for amphetamine in rodent drug discrimination tests. + Activities of 2-aminoindanes and amphetamine relatives Compound Monoamine release (EC50 half-maximal effective concentration, nM) Ref Serotonin Norepinephrine Dopamine 2-AI >10,000 86 439 MDAI 114 117 1,334 MMAI 31 3,101 >10,000 MEAI 134 861 2,646 d-Amphetamine 698–1,765 6.6–7.2 5.8–24.8 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 Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products Neuropsychopharmacology 38 4 552–562 March 2013 23072836 3572453 10.1038/npp.2012.204 Blough B Dopamine-releasing agents Trudell ML, Izenwasser S Dopamine Transporters: Chemistry, Biology and Pharmacology 305–320 July 2008 978-0-470-11790-3 181862653 OL18589888W Wiley Hoboken [NJ] https://books.google.com/books?id=QCagLAAACAAJ https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf Glennon RA, Dukat M Neuropharmacology of New Psychoactive Substances (NPS) Structure-Activity Relationships of Synthetic Cathinones Current Topics in Behavioral Neurosciences 32 19–47 2017 27830576 5818155 10.1007/7854_2016_41 978-3-319-52442-9 Partilla JS, Dersch CM, Baumann MH, Carroll FI, Rothman RB 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 1–476 (252) 1999 11680410 https://archives.nida.nih.gov/sites/default/files/180.pdf#page=261 https://web.archive.org/web/20230805004105/https://archives.nida.nih.gov/sites/default/files/180.pdf#page=261 dead August 5, 2023 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). [...] MDA 160–162 47–108 106–190 MDMA 50–85 54–110 51–278 Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin Synapse 39 1 32–41 January 2001 11071707 10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 15573624 Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue Neuropsychopharmacology 37 5 1192–1203 April 2012 22169943 3306880 10.1038/npp.2011.304 Marusich JA, Antonazzo KR, Blough BE, Brandt SD, Kavanagh PV, Partilla JS, Baumann MH 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 26362361 4681602 10.1016/j.neuropharm.2015.09.004 Setola V, Hufeisen SJ, Grande-Allen KJ, Vesely I, Glennon RA, Blough B, Rothman RB, Roth BL 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 12761331 10.1124/mol.63.6.1223 839426 Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH 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 32875347 10.1007/s00213-020-05648-z 7686291 3-MA ND No data 58.0 103 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: Halberstadt AL, Brandt SD, Walther D, Baumann MH 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 30904940 6848746 10.1007/s00213-019-05207-1 Chemistry Synthesis The chemical synthesis of 2-aminoindane was reported. For example, a 79% yield was reported from indene and ammonia precursors.((Yasuda, M.)), ((Kojima, R.)), ((Tsutsui, H.)), ((Utsunomiya, D.)), ((Ishii, K.)), ((Jinnouchi, K.)), ((Shiragami, T.)), ((Yamashita, T.)) The Journal of Organic Chemistry Redox-Photosensitized Aminations of 1,2-Benzo-1,3-cycloalkadienes, Arylcyclopropanes, and Quadricyclane with Ammonia 68 20 7618–7624 1 October 2003 https://pubs.acs.org/doi/10.1021/jo030053%2B 10.1021/jo030053+ subscription The older method uses 1-indanone as the starting material.((Levin, N.)), ((Graham, B. E.)), ((Kolloff, H. G.)) The Journal of Organic Chemistry PHYSIOLOGICALLY ACTIVE INDANAMINES 1 09 4 380–391 July 1944 https://pubs.acs.org/doi/abs/10.1021/jo01186a010 10.1021/jo01186a010 subscription Analogues 2-AI is a rigid analogue of amphetamine and has similar effects in rodents. Oberlender R, Nichols DE Structural variation and (+)-amphetamine-like discriminative stimulus properties Pharmacology, Biochemistry, and Behavior 38 3 581–6 March 1991 2068194 10.1016/0091-3057(91)90017-V 19069907 https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=77437efa02b4a0f688e4038b153ddfafde6da614 subscription Glennon RA, Young R, Hauck AE, McKenney JD Structure-activity studies on amphetamine analogs using drug discrimination methodology Pharmacol Biochem Behav 21 6 895–901 December 1984 6522418 10.1016/s0091-3057(84)80071-4 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 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-AB 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.Hathaway BA, Nichols DE, Nichols MB, Yim GK A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene Journal of Medicinal Chemistry 25 5 535–538 May 1982 6123601 10.1021/jm00347a011 Derivatives 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-AINichols DE, Weintraub HJ, Pfister WR, Yim GK The Use of Rigid Analogues to Probe Hallucinogen Receptors 70–83 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 https://books.google.com/books?id=0DnIVGMykn4C https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=7ec3b34f01bca1140244abd0c87473cf38701e50#page=81 Nichols DE, Barfknecht CF, Long JP, Standridge RT, Howell HG, Partyka RA, Dyer DC Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP) J Med Chem 17 2 161–166 February 1974 4809251 10.1021/jm00248a004 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 Legal status China As of October 2015 2-AI is a controlled substance in China.http://www.sfda.gov.cn/WS01/CL0056/130753.html 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 China Food and Drug Administration 27 September 2015 Chinese 1 October 2015 https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html 1 October 2015 dead Finland Scheduled in the "Government decree on psychoactive substances banned from the consumer market".https://finlex.fi/fi/lainsaadanto/2014/1130 FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014 Sweden Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/juni/atta-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/ Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara Eight substances are proposed to be classified as narcotics or dangerous to health Folkhälsomyndigheten sv 24 June 2019 11 November 2019 18 November 2019 https://web.archive.org/web/20191118191453/https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/juni/atta-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/ dead United States 2-Aminoindane is not scheduled at the federal level in the United States,http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. 2018-02-14 2009-08-27 https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm dead 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 Substituted 2-aminoindane Cyclized phenethylamine 1-Aminoindane 1-Aminomethylindane 2-Aminotetralin References External links 2-AI (2-Aminoindane) - Isomer Design 2-Aminoindane - PsychonautWiki 2-Aminoindan - Erowid Category:2-Aminoindanes Category:Designer drugs Category:Norepinephrine reuptake inhibitors Category:Norepinephrine-dopamine releasing agents Category:Stimulants