2-Aminotetralin

Chemical compound changed 477212588 2-Aminotetralin.svg skin-invert-image 200px Uncontrolled Oral Norepinephrine–dopamine releasing agent; Stimulant None correct CAS 2954-50-9 correct FDA LGX8T83G7X 34677 correct chemspider 31912 correct EBI 30294 2-AT; 1,2,3,4-Tetrahydronaphthalen-2-amine; THN 1,2,3,4-tetrahydronaphthalen-2-amine 10 13 1 C1CC2=CC=CC=C2CC1N correct chemspider 1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 correct chemspider LCGFVWKNXLRFIF-UHFFFAOYSA-N 2-Aminotetralin (2-AT), also known as 1,2,3,4-tetrahydronaphthalen-2-amine (THN), is a stimulant drug of the 2-aminotetralin family with a chemical structure consisting of a tetralin core with an amine as substituent. Oberlender R, Nichols DE 19069907 Structural variation and (+)-amphetamine-like discriminative stimulus properties Pharmacology, Biochemistry, and Behavior 38 3 581–586 March 1991 2068194 10.1016/0091-3057(91)90017-V https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=77437efa02b4a0f688e4038b153ddfafde6da614 In previous studies, 2-AT either did not stimulate spontaneous motor activity in mice (1,8), or it had 10% of the activity of amphetamine (24). Yet, in the present study, it mimicked (+)-amphetamine as a DS in rats, in agreement with the results of Glennon et al. (7). However, 2-AT was one-half as potent as (+)-amphetamine in that study but only one-eighth as potent as (+)-amphetamine in the present experiment. subscription Marley E, Stephenson JD Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections British Journal of Pharmacology 42 4 522–542 August 1971 5116035 1665761 10.1111/j.1476-5381.1971.tb07138.x 2-AT is a rigid analogue of phenylisobutylamine and fully substitutes for d-amphetamine in rat drug discrimination tests, although at one-half to one-eighth the potency. 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 It showed greater potency than a variety of other amphetamine homologues, including 2-amino-1,2-dihydronapthalene (2-ADN), 2-aminoindane (2-AI), 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 2-AT has been shown to inhibit the reuptake of serotonin and norepinephrine, and might induce their release as well. Bruinvels J Evidence for inhibition of the reuptake of 5-hydroxytryptamine and noradrenaline by tetrahydronaphthylamine in rat brain British Journal of Pharmacology 42 2 281–286 June 1971 5091160 1667157 10.1111/j.1476-5381.1971.tb07109.x Bruinvels J, Kemper GC Role of noradrenaline and 5-hydroxytryptamine in tetrahydronaphthylamine-induced temperature changes in the rat British Journal of Pharmacology 43 1 1–9 September 1971 4257629 1665934 10.1111/j.1476-5381.1971.tb07151.x It is also likely to act on dopamine on account of its full substitution of d-amphetamine in rodent studies. Chemical derivatives A number of derivatives of 2-aminotetralin exist, including: 15em 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 CHF-1024 DOM-ATNichols 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 MDAT MDMAT Nolomirole UCD0830 UH-232 See also Substituted 2-aminotetralin 1-Aminotetralin Aminoindane 3-Aminochroman References External links 2-AT (2-Aminotetralin) - Isomer Design * Category:Serotonin-norepinephrine-dopamine releasing agents Category:Stimulants