7-AB

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Infobox drug

| drug_name =

| image = 7-AB.svg

| width =

| caption =

| pronounce =

| tradename =

| Drugs.com =

| MedlinePlus =

| licence_CA =

| licence_EU =

| DailyMedID =

| licence_US =

| pregnancy_AU =

| pregnancy_category =

| dependency_liability =

| addiction_liability =

| routes_of_administration =

| class =

| ATC_prefix =

| ATC_suffix =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life =

| duration_of_action =

| excretion =

| CAS_number = 450-60-2

| CAS_supplemental =

| PubChem = 11789519

| PubChemSubstance =

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID = 9964193

| UNII =

| KEGG =

| ChEBI =

| ChEMBL =

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = 6,7,8,9-Tetrahydro-5H-benzocyclohepten-7-ylamine

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

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

| SMILES = C1CC2=CC=CC=C2CCC1N

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

| StdInChIKey = BGKVEHAWZXNHBI-UHFFFAOYSA-N

}}

7-AB, also known as 7-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 thesis | vauthors = Vekariya R | degree = Master of Science | publisher = Virginia Commonwealth University | title=Towards Understanding the Mechanism of Action of Abused Cathinones | via = 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 = Pharmacol Biochem Behav | volume = 21 | issue = 6 | pages = 895–901 | date = December 1984 | pmid = 6522418 | doi = 10.1016/s0091-3057(84)80071-4 | url = | 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]. [...] }} Unlike amphetamine, 2-AI, and 2-AT, 7-AB did not produce stimulant-type effects in animals. Instead, it caused behavioral disruption and death at higher doses. 6-AB is a positional isomer of 7-AB.