Bucladesine

CAT: 0804-HY-B0764BSize: 1 EachDry Ice: NoHazardous: No

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CAT#:0804-HY-B0764BSize:1 Each

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Description

Bucladesine (DBcAMP) is a membrane permeable selective activator that activates cyclic adenosine phosphate dependent protein kinase A (PKA) . The main regulatory mechanism of Bucladesine involves the cAMP/PKA signaling pathway. When Bucladesine activates PKA, it can promote a variety of cellular processes, including neurodevelopment, growth and plasticity. In particular, the cAMP/PKA signaling pathway plays a key role in the expression of long-term enhancement (LTP) and long-term inhibition (LTD), as well as in the formation of long-term memory in the hippocampus. Bucladesine can be used to study memory formation and neuroplasticity[1].

CAS Number

362-74-3

Product Name Alternative

Dibutyryl cAMP; DBcAMP

UNSPSC

12352005

Hazard Statement

H315-H319

Target

PKA

Type

Reference compound

Related Pathways

Stem Cell/Wnt; TGF-beta/Smad

Applications

Neuroscience-Neuromodulation

Field of Research

Neurological Disease

Assay Protocol

https://www.medchemexpress.com/bucladesine.html

Solubility

10 mM in DMSO

Smiles

O=C(CCC)O[C@H]1[C@H](N2C(N=CN=C3NC(CCC)=O)=C3N=C2)O[C@@](CO4)([H])[C@@]1([H])OP4(O)=O

Molecular Formula

C18H24N5O8P

Molecular Weight

469.39

Precautions

P264-P280-P302+P352-P362+P364

References & Citations

[1]Sharifzadeh M, et al. Post-training intrahippocampal infusion of nicotine–bucladesine combination causes a synergistic enhancement effect on spatial memory retention in rats[J]. European journal of pharmacology, 2007, 562 (3) : 212-220.

Shipping Conditions

Room temperature

Scientific Category

Reference compound1

Clinical Information

Launched

Chemical Information

Bucladesine

Bucladesine is a 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP. It has a role as a vasodilator agent, a cardiotonic drug and an agonist. It is a 3',5'-cyclic purine nucleotide, a member of butanamides and a butyrate ester. It is functionally related to a 3',5'-cyclic AMP.

CAS Number	362-74-3
PubChem CID	9687
IUPAC Name	[(4aR,6R,7R,7aR)-6-[6-(butanoylamino)purin-9-yl]-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate
Molecular Formula	C18H24N5O8P
Molecular Weight	469.4
XLogP	-0.5
Topological Polar Surface Area	164
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	8
Heavy Atom Count	32
Formal Charge	0
Complexity	759

SMILES

CCCC(=O)NC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)OC(=O)CCC

InChI

InChI=1S/C18H24N5O8P/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24)/t10-,14-,15-,18-/m1/s1

InChIKey

CJGYSWNGNKCJSB-YVLZZHOMSA-N

Chemical Structure

2D Structure

CAS: 362-74-3

CID: 9687

Formula: C18H24N5O8P

MW: 469.4

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	469.4
XLogP3	-0.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	8
Exact Mass	469.13624974
Monoisotopic Mass	469.13624974
Topological Polar Surface Area	164 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	759
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
MBS5756385	Bucladesine
T1418-01	Bucladesine sodium
C03352-250mg	Bucladesine calcium
ENZ-CHM363-0100	Bucladesine . sodium
TMIH-0126-01	Bucladesine-d14
443554-01	Bucladesine Calcium Salt
AR-B02148-01	Bucladesine Impurity 2
C13006-01	Dibutyryl-cAMP (Bucladesine)
295803-01	Bucladesine Sodium Salt

Bucladesine

Chemical Information

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