(-)-(1S,4R)-4-Aminocyclopent-2-ene-1-carboxylic acid
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(-)-(1S,4R)-4-Aminocyclopent-2-ene-1-carboxylic acid

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(-)-(1S,4R)-4-Aminocyclopent-2-enecarboxylic Acid is a cyclopentane GABA analogue.

Category
Cyclic Amino Acids
Catalog number
BAT-006610
CAS number
168471-40-7
Molecular Formula
C6H9NO2
Molecular Weight
127.14
(-)-(1S,4R)-4-Aminocyclopent-2-ene-1-carboxylic acid
IUPAC Name
(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid
Synonyms
(-)-(1S,4R)-4-Aminocyclopent-2-enecarboxylic acid
Appearance
Off-white powder
Purity
≥ 99% (HPLC)
Density
1.249 g/cm3
Melting Point
180 °C
Boiling Point
266.55°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C6H9NO2/c7-5-2-1-4(3-5)6(8)9/h1-2,4-5H,3,7H2,(H,8,9)/t4-,5+/m1/s1
InChI Key
VTCHZFWYUPZZKL-UHNVWZDZSA-N
Canonical SMILES
C1C(C=CC1N)C(=O)O
1.Systemic administration of 1R,4S-4-amino-cyclopent-2-ene-carboxylic acid, a reversible inhibitor of GABA transaminase, blocks expression of conditioned place preference to cocaine and nicotine in rats.
Ashby CR Jr1, Paul M, Gardner EL, Gerasimov MR, Dewey SL, Lennon IC, Taylor SJ. Synapse. 2002 May;44(2):61-3.
We examined the effect of 1R,4S-4-amino-cyclopent-2-ene-carboxylic acid (ACC), a reversible inhibitor of GABA transaminase, on the expression of conditioned place preference response to cocaine and nicotine in rats. Cocaine (20 mg/kg i.p.) and nicotine (0.4 mg/kg s.c.), but not vehicle or 300 mg/kg i.p. of ACC, produced a significant conditioned place preference response. Pretreatment of animals with 300 and 75 mg/kg i.p. of ACC significantly attenuated the expression of the cocaine- and nicotine-induced conditioned place preference responses, respectively. These results are the first to suggest that reversible inhibition of GABA transaminase may be useful in blocking cue-induced relapse to nicotine and cocaine.
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