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Merck

C3021

Dicyanocobinamide

≥93%

Synonym(s):

Cobinamide dicyanide, Etiocobalamin, Factor B

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About This Item

Empirical Formula (Hill Notation):
C50H72CoN13O8
CAS Number:
27792-36-5
Molecular Weight:
1042.12
NACRES:
NA.79
PubChem Substance ID:
24892558
UNSPSC Code:
12352205
MDL number:
MFCD00056330

Key Documents

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InChI

1S/C48H73N11O8.2CN.Co/c1-23(60)22-55-38(67)16-17-45(6)29(18-35(52)64)43-48(9)47(8,21-37(54)66)28(12-15-34(51)63)40(59-48)25(3)42-46(7,20-36(53)65)26(10-13-32(49)61)30(56-42)19-31-44(4,5)27(11-14-33(50)62)39(57-31)24(2)41(45)58-43;2*1-2;/h19,23,26-29,43,59-60H,10-18,20-22H2,1-9H3,(H2,49,61)(H2,50,62)(H2,51,63)(H2,52,64)(H2,53,65)(H2,54,66)(H,55,67);;;/b30-19-,39-24-,40-25-;;;/t23-,26+,27+,28+,29-,43?,45+,46-,47-,48-;;;/m0.../s1

SMILES string

N#C[Co]C#N.C[C@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2N=C1C(C)=C3N=C(C=C4N=C(C(C)=C5N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]5CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)C(C)(C)[C@@H]3CCC(N)=O

InChI key

NJATWHPHZUGTHR-GXEWULDJSA-N

biological source

synthetic (organic)

assay

≥93%

form

powder

impurities

≤0.1% vitamin B12

color

purple to very dark purple

storage temp.

−20°C

Quality Level

200

Related Categories

General description

Dicyanocobinamide, also known as factor b is a coenzyme B12 precursor. It has a corrin ring structure with four of the six coordination sites of the cobalt (Co) atom being the pyrrole nitrogen atoms.

Application

Dicyanocobinamide has been used for the crystallization of vitamin B12-binding protein (BtuF). It has also been used for the destabilization of BtuCD-BtuF Interaction.
For use in determining non-intrinsic factor (R protein) in intrinsic factor preparations.

Biochem/physiol Actions

Dicyanocobinamide (Cbi) functions as a soluble guanylate cyclase (sGC) co-activator and targets the N-terminal regulatory regions. This action is similar to the effect of forskolin on adenylyl cyclases. Dicyanocobinamide elevates the intracellular cyclic guanosine monophosphate (cGMP) levels and exhibits vasorelaxant activity in rats. It is used along with various cobalamins in studies of the inhibition of HIV-1 integrase and nitric oxide synthase.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Class I Designated Chemical Substances

prtr

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

C3021-VAR: + C3021-250MG: + C3021-50MG:4548173191287 + C3021-10MG:4548173191270 + C3021-BULK: + C3021PROC:

jan

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Inhibition of nitric oxide synthase by cobalamins and cobinamides
Weinberg JB, et al.
Free Radical Biology & Medicine, 46(12), 1626-1632 (2009)
Anne-Sophie Ruget et al.
Frontiers in veterinary science, 6, 455-455 (2020-01-11)
Peste des petits ruminants virus (PPRV), responsible for peste des petits ruminants (PPR), is widely circulating in Africa and Asia. The disease is a huge burden for the economy and development of the affected countries. In Eastern Africa, the disease
The Different Effects of Substrates and Nucleotides on the Complex Formation of ABC Transporters
Fiorentino F, et al.
Structure, 27(4), 651-659 (2019)
Conformational change of a tryptophan residue in BtuF facilitates binding and transport of cobinamide by the vitamin B12 transporter BtuCD-F
Mireku SA, et al.
Scientific reports, 7, 41575-41575 (2017)
Longxing Cao et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(47), 13438-13443 (2016-11-09)
Clearance of dead cells is critical for maintaining homeostasis and prevents autoimmunity and inflammation. When cells undergo apoptosis and necrosis, specific markers are exposed and recognized by the receptors on phagocytes. DEC205 (CD205) is an endocytotic receptor on dendritic cells
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