trans-4-Allyl-L-proline hydrochloride
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trans-4-Allyl-L-proline hydrochloride

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trans-4-Allyl-L-proline hydrochloride is used as a potential treatment for addiction and neurological disorders due to its ability to modulate neurotransmitter systems in the brain. It has shown promise in preclinical studies for reducing drug-seeking behavior and improving cognitive function.

Category
Cyclic Amino Acids
Catalog number
BAT-007005
CAS number
1049755-14-7
Molecular Formula
C8H14ClNO2
Molecular Weight
191.65
trans-4-Allyl-L-proline hydrochloride
IUPAC Name
(2S,4R)-4-prop-2-enylpyrrolidine-2-carboxylic acid;hydrochloride
Synonyms
L-Proline, 4-(2-propen-1-yl)-, hydrochloride (1:1), (4R)-; H-Pro(4-Allyl)-OH HCl; (R)-γ-Allyl-L-proline HCl; (2S,4R)-4-Allylpyrrolidine-2-carboxylic acid hydrochloride
Related CAS
393524-70-4 (free base)
Appearance
Off-white to white powder
Purity
≥95%
Storage
Store at 2-8°C under inert gas (nitrogen or Argon)
InChI
InChI=1S/C8H13NO2.ClH/c1-2-3-6-4-7(8(10)11)9-5-6;/h2,6-7,9H,1,3-5H2,(H,10,11);1H/t6-,7+;/m1./s1
InChI Key
QOKUYUBQOIDWLE-HHQFNNIRSA-N
Canonical SMILES
C=CCC1CC(NC1)C(=O)O.Cl
1.Discovery of (2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid hydrochloride (GAP-134)13, an orally active small molecule gap-junction modifier for the treatment of atrial fibrillation.
Butera JA1, Larsen BD, Hennan JK, Kerns E, Di L, Alimardanov A, Swillo RE, Morgan GA, Liu K, Wang Q, Rossman EI, Unwalla R, McDonald L, Huselton C, Petersen JS. J Med Chem. 2009 Feb 26;52(4):908-11. doi: 10.1021/jm801558d.
Rotigaptide (3) is an antiarrhythmic peptide that improves cardiac conduction by modifying gap-junction communication. Small molecule gap-junction modifiers with improved physical properties were identified from a Zealand Pharma peptide library using pharmaceutical profiling, established SAR around 3, and a putative pharmacophore model for rotigaptide. Activity of the compounds was confirmed in a mouse cardiac conduction block model of arrhythmia. Dipeptide 9f (GAP-134) was identified as a potent, orally active gap-junction modifier for clinical development.
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