6-AB

6-AB
Clinical data
Other names	6-Amino-6,7,8,9-tetrahydro-5H-benzocycloheptene
ATC code	None;
Identifiers
	IUPAC name 6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amine;
CAS Number	57559-72-5;
PubChem CID	41896;
ChemSpider	38228;
ChEMBL	ChEMBL1190678;
Chemical and physical data
Formula	C11H15N
Molar mass	161.248 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC(CC2=CC=CC=C2C1)N;
	InChI InChI=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; Key: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).^[1]^[2]^[3] Unlike amphetamine, 2-AI, and 2-AT, 6-AB did not produce stimulant-type effects in animals.^[1]^[2] In another study, it produced a biphasic effect at high doses, with initial hypolocomotion followed after a few hours by weak locomotor stimulation.^[2]^[3] 7-AB is a positional isomer of 6-AB.^[1]^[2]

References

1 2 3 Vekariya R (2012). "Towards Understanding the Mechanism of Action of Abused Cathinones". VCU Theses and Dissertations. doi:10.25772/AR93-7024. 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
1 2 3 4 Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior. 21 (6): 895–901. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418. 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]. [...]
1 2 Vejdělek ZJ, Dlabač A, Protiva M (1974). "6-Amino-6,7,8,9-tetrahydro-5H-benzocycloheptene and derivatives". Collection of Czechoslovak Chemical Communications. 39 (10): 2819–2827. doi:10.1135/cccc19742819. ISSN 0010-0765.

External links

6-AB - isomer design

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[Vekariya2012-1] 1 2 3 Vekariya R (2012). "Towards Understanding the Mechanism of Action of Abused Cathinones". VCU Theses and Dissertations. doi:10.25772/AR93-7024. 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

[GlennonYoungHauck1984-2] 1 2 3 4 Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior. 21 (6): 895–901. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418. 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]. [...]

[VejdělekDlabačProtiva1974-3] 1 2 Vejdělek ZJ, Dlabač A, Protiva M (1974). "6-Amino-6,7,8,9-tetrahydro-5H-benzocycloheptene and derivatives". Collection of Czechoslovak Chemical Communications. 39 (10): 2819–2827. doi:10.1135/cccc19742819. ISSN 0010-0765.

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6-AB

See also

References

External links