| Revision as of 17:13, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 451222764 of page 2-Aminotetralin for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 06:02, 8 December 2024 edit 76.174.0.57 (talk) Add missing analogue. |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 407810685 |
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| verifiedrevid = 477212588 |
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| IUPAC_name = 1,2,3,4-tetrahydronaphthalen-2-amine |
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| IUPAC_name = 1,2,3,4-tetrahydronaphthalen-2-amine |
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| image = 2-Aminotetralin.png |
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| image = 2-Aminotetralin Structure.svg |
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| width = |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = <!-- blanked - oldvalue: 2954-50-9 --> |
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| CAS_number = 2954-50-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = LGX8T83G7X |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=10 | H=13 | N=1 |
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| C=10 | H=13 | N=1 |
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| molecular_weight = 147.217 g/mol |
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| smiles = C1CC2=CC=CC=C2CC1N |
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| smiles = C1CC2=CC=CC=C2CC1N |
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| InChI = 1/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 |
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| InChIKey = LCGFVWKNXLRFIF-UHFFFAOYAA |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 |
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| StdInChI = 1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 |
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| StdInChIKey = LCGFVWKNXLRFIF-UHFFFAOYSA-N |
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| StdInChIKey = LCGFVWKNXLRFIF-UHFFFAOYSA-N |
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}} |
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}} |
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'''2-Aminotetralin''' ('''2-AT'''), also known as '''1,2,3,4-tetrahydronaphthalen-2-amine''' ('''THN'''), is a ] ] with a ] consisting of a ] ] combined with an ].<ref name="OberlenderNichols1991">{{cite journal | vauthors = Oberlender R, Nichols DE | s2cid = 19069907 | title = Structural variation and (+)-amphetamine-like discriminative stimulus properties | journal = Pharmacology, Biochemistry, and Behavior | volume = 38 | issue = 3 | pages = 581–586 | date = March 1991 | pmid = 2068194 | doi = 10.1016/0091-3057(91)90017-V | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=77437efa02b4a0f688e4038b153ddfafde6da614 | quote = 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. }}</ref><ref name="MarleyStephenson1971">{{cite journal | vauthors = Marley E, Stephenson JD | title = Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections | journal = British Journal of Pharmacology | volume = 42 | issue = 4 | pages = 522–542 | date = August 1971 | pmid = 5116035 | pmc = 1665761 | doi = 10.1111/j.1476-5381.1971.tb07138.x }}</ref> |
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2-AT is a rigid ] of ] and fully substitutes for ] in rat ] tests, although at one-half to one-eighth the ].<ref name="OberlenderNichols1991" /><ref name="GlennonYoungHauck1984">{{cite journal | vauthors = Glennon RA, Young R, Hauck AE, McKenney JD | title = Structure-activity studies on amphetamine analogs using drug discrimination methodology | journal = Pharmacol Biochem Behav | volume = 21 | issue = 6 | pages = 895–901 | date = December 1984 | pmid = 6522418 | doi = 10.1016/s0091-3057(84)80071-4 | url = }}</ref> It showed greater potency than a variety of other amphetamine homologues, including ] (2-ADN), ] (2-AI), ] (1-NAP), ] (2-NAP), ] (1-PP), {{Abbrlink|6-AB|6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene}}, and {{Abbrlink|7-AB|7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene}}.<ref name="GlennonYoungHauck1984" /><ref name="OberlenderNichols1991" /><ref name="HathawayNicholsYim1982">{{cite journal |vauthors=Hathaway BA, Nichols DE, Nichols MB, Yim GK | title = A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene | journal = Journal of Medicinal Chemistry | volume = 25 | issue = 5 | pages = 535–538 |date=May 1982 | pmid = 6123601 | doi = 10.1021/jm00347a011}}</ref> |
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2-AT has been shown to ] the ] of ] and ], and might induce their ] as well.<ref name="Bruinvels1971">{{cite journal | vauthors = Bruinvels J | title = Evidence for inhibition of the reuptake of 5-hydroxytryptamine and noradrenaline by tetrahydronaphthylamine in rat brain | journal = British Journal of Pharmacology | volume = 42 | issue = 2 | pages = 281–286 | date = June 1971 | pmid = 5091160 | pmc = 1667157 | doi = 10.1111/j.1476-5381.1971.tb07109.x }}</ref><ref name="BruinvelsKemper1971">{{cite journal | vauthors = Bruinvels J, Kemper GC | title = Role of noradrenaline and 5-hydroxytryptamine in tetrahydronaphthylamine-induced temperature changes in the rat | journal = British Journal of Pharmacology | volume = 43 | issue = 1 | pages = 1–9 | date = September 1971 | pmid = 4257629 | pmc = 1665934 | doi = 10.1111/j.1476-5381.1971.tb07151.x }}</ref> It is also likely to act on ] on account of its full substitution of d-amphetamine in ].<ref name="OberlenderNichols1991" /><ref name="GlennonYoungHauck1984" /> |
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== Chemical derivatives == |
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A number of ]s of 2-aminotetralin exist, including: |
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== References == |
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{{Reflist|2}} |
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{{Stimulants}} |
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{{Monoamine releasing agents}} |
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{{DEFAULTSORT:Aminotetralin, 2-}} |
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] |
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] |
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] |