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Merck
CN

C3607

Cyanocobalamin

meets USP testing specifications

Synonym(s):

Vitamin B12, α-(5,6-Dimethylbenzimidazolyl)cyanocobamide, CN-Cbl, Cyanocob(III)alamin, Cyanocobalamin

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About This Item

Empirical Formula (Hill Notation):
C63H88CoN14O14P
CAS Number:
68-19-9
Molecular Weight:
1355.37
MDL number:
MFCD00151092
UNSPSC Code:
12352205
eCl@ss:
34058004
PubChem Substance ID:
24892627
EC Number:
200-680-0
NACRES:
NA.21
Beilstein/REAXYS Number:
4122889

Key Documents

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Product Name

Cyanocobalamin, meets USP testing specifications

SMILES string

C/C(C1=N[C@]([C@]([C@H](CC(N)=O)[C@@]/2(C)CCC(NC[C@@H](OP([O-])(O[C@H]3[C@@H](O)[C@@H](N4C=[N]5C6=C4C=C(C)C(C)=C6)O[C@@H]3CO)=O)C)=O)([H])N([Co+]5C#N)C2=C(C)/C([C@@H](CCC(N)=O)C/7(C)C)=NC7=C/8)(C)[C@@](C)(CC(N)=O)[C@@H]1CCC(N)=O)=C9N=C8[C@@H](CCC(N)=O)[C@

InChI

1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57?,59-,60+,61+,62+;;/m1../s1

InChI key

RMRCNWBMXRMIRW-QJRSUKKJSA-L

agency

USP/NF
meets USP testing specifications

assay

96.0-102.0% dry basis

form

powder

color

dark red

application(s)

pharmaceutical (small molecule)

storage temp.

2-8°C

Quality Level

200

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Application

Cyanocobalamin has been used to study its effects on the prevention of colon cancer.
Required for growth, genetic stability and survival of cells in vitro. Functions to support one-carbon metabolism. Present in many classical and serum-free formulations.

Biochem/physiol Actions

Cyanocobalamin is used in the preparation of multivitamin supplements and fortified food. It acts as a coenzyme to convert L-methylmalonyl CoA to succinyl CoA, which is catalyzed by isomerase. Cyanocobalamin is used to treat vitamin B12 deficiency. Cyanocobalamin meets USP testing specifications.

General description

Cyanocobalamin (B12) is a water soluble vitamin, which is mainly found in animal products, like dairy products, meat and eggs. It belongs to the B12 class of vitamins, commonly called as cobalamins. Cyanocobalamin consists of four pyrrole rings with a central cobalt atom coordinated by four equatorial nitrogen ligands.

Storage Class

11 - Combustible Solids

wgk

WGK 1

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000455525
0000455525
0000497663
0000497663
0000448733

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Oral cyanocobalamin supplementation in older people with vitamin B12 deficiency: a dose-finding trial
Eussen SJPM, et al.
Archives of Internal Medicine, 165(10), 1167-1172 (2005)
Dose-Dependent Effect of Cyanocobalamin on the Prevention of Colon Cancer: An In Vivo Study
Padmanabhan S, et al.
EC nutrition, 13, 563-571 (2018)
Tóshiko Takahashi-Iñiguez et al.
Journal of Zhejiang University. Science. B, 13(6), 423-437 (2012-06-05)
Vitamin B(12) is an organometallic compound with important metabolic derivatives that act as cofactors of certain enzymes, which have been grouped into three subfamilies depending on their cofactors. Among them, methylmalonyl-CoA mutase (MCM) has been extensively studied. This enzyme catalyzes
Determination of cyanocobalamin by isotope dilution LC-MS/MS
D Ulivo L, et al.
Analytica Chimica Acta, 990, 103-109 (2017)
Bert-Ram Sah et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 55(1), 43-49 (2013-12-18)
Targeting cancer cells with vitamin B12 (cobalamin) is hampered by unwanted physiologic tissue uptake mediated by transcobalamin. Adhering to good manufacturing practice, we have developed a new (99m)Tc-cobalamin derivative ((99m)Tc(CO)3-[(4-amido-butyl)-pyridin-2-yl-methyl-amino-acetato] cobalamin, (99m)Tc-PAMA-cobalamin). The derivative shows no binding to transcobalamin but
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