6-AB

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| image = 6-AB.svg

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| CAS_number = 57559-72-5

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| PubChem = 41896

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| ChemSpiderID = 38228

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| ChEMBL = 1190678

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| synonyms = 6-Amino-6,7,8,9-tetrahydro-5H-benzocycloheptene

| IUPAC_name = 6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amine

| C=11 | H=15 | N=1

| SMILES = C1CC(CC2=CC=CC=C2C1)N

| StdInChI = 1S/C11H15N/c12-11-7-3-6-9-4-1-2-5-10(9)8-11/h1-2,4-5,11H,3,6-8,12H2

| StdInChIKey = MDVRGZASGHPBAG-UHFFFAOYSA-N

}}

6-AB, also known as 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, is a conformationally restricted analogue of amphetamine related to 2-aminoindane (2-AI) and 2-aminotetralin (2-AT).{{cite journal | vauthors = Vekariya R | title=Towards Understanding the Mechanism of Action of Abused Cathinones | journal=VCU Theses and Dissertations | date=2012 | doi=10.25772/AR93-7024 | quote=The side chain conformations of various phenylisopropylamines have been studied by nuclear magnetic resonance, and suggest that in solution, an extended trans-phenylamino arrangement is preferred.29 Some of the conformationally restricted analogs of phenylalkylamines mimic this conformation.29 For example 2-aminotetralin (2-AT, 17) mimics this to some extent, while 2-aminoindane (2-AI, 18) to a lesser extent. It was found that 2-AI (18) and in particular 2-AT (17) are capable of producing various amphetamine-like effects, including anorexia and locomotor stimulation in animals.29 Four conformationally restricted analogs, 2-AI (18), 2-AT (17), 6-amino- and 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene (6-AB, 19 and 7-AB, 20, respectively) were studied and it was found that 2-AT (17) is most similar to racemic amphetamine in potency and may be the conformation that best mimics amphetamine necessary for producing amphetamine-like stimulant effects, however, compounds 19 and 20 failed to produce amphetamine-like stimulant effect.29 The racemic aminotetralin 17 produced 10% the locomotor stimulant action of amphetamine in mice, whereas 18 was inactive at the highest doses tested.21}}{{cite journal | vauthors = Glennon RA, Young R, Hauck AE, McKenney JD | title = Structure-activity studies on amphetamine analogs using drug discrimination methodology | journal = Pharmacology, Biochemistry, and Behavior | volume = 21 | issue = 6 | pages = 895–901 | date = December 1984 | pmid = 6522418 | doi = 10.1016/s0091-3057(84)80071-4 | quote = Both 6-amino- and 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, 6-AB and 7-AB, [...]. Stimulus generalization was not observed to occur with phenethylamine, 1-NAP, 2-NAP, 1-PP, 6-AB, 7-AB, or α-demethylcathinone (Table 1). [...] 6-AB produced saline-appropriate responding at doses of up to 20 mg/kg, whereas 7-AB produced similar responding at 17.5 mg/kg and disruption of behavior at 20 and 25 mg/kg. All four animals treated with 25 mg/kg of 7-AB died within 24 hours of administration of drug. [...] Most of the agents employed in this study have been previously examined for amphetamine-like properties. For example, 2-AI and 2-AT produce anorectic effects in animals, with 2-AI apparently being the more active [23]. Phenethylamine, 1-NAP and 2-NAP are inactive as locomotor stimulants in rodents; while 2-AI and 2-AT produce locomotor stimulation, both are less active than amphetamine [23,31]. At high doses, 6-AB produces a biphasic effect, an initial locomotor depressant action followed, after approximately two to three hours, by weak locomotor stimulation [32]. [...] 2-AT is more active than 2-AI in producing rotational behavior in 6-hydroxydopamine-lesioned rats, while 6-AB is inactive at 10 mg/kg [3]. [...] }}{{cite journal | vauthors = Vejdělek ZJ, Dlabač A, Protiva M | title=6-Amino-6,7,8,9-tetrahydro-5H-benzocycloheptene and derivatives | journal=Collection of Czechoslovak Chemical Communications | volume=39 | issue=10 | date=1974 | issn=0010-0765 | doi=10.1135/cccc19742819 | pages=2819–2827}} Unlike amphetamine, 2-AI, and 2-AT, 6-AB did not produce stimulant-type effects in animals. In another study, it produced a biphasic effect at high doses, with initial hypolocomotion followed after a few hours by weak locomotor stimulation. 7-AB is a positional isomer of 6-AB.