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Merck

43107

Cyanocobalamin

tested according to Ph. Eur.

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
PubChem Substance ID:
329756307
UNSPSC Code:
12352205
MDL number:
MFCD00151092
NACRES:
NA.21
EC Number:
200-680-0
Beilstein/REAXYS Number:
4122889

Product Name

Cyanocobalamin, tested according to Ph. Eur.

InChI key

RMRCNWBMXRMIRW-QJRSUKKJSA-L

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

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@

biological source

fermentation/recombinant

Quality Level

100

agency

tested according to Ph. Eur.

assay

96.0-102.0% dry basis

form

powder

color

dark red

solubility

water: soluble 1 gm in 80 ml
acetone: insoluble
alcohol: soluble
chloroform: insoluble
diethyl ether: insoluble

application(s)

cell analysis

storage temp.

2-8°C

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Application

Cyanocobalamin was added in the assay buffer during the analysis step of ELISA for ensuring that all transcobalamin was saturated with cobalamin before analysis. Cyanocobalamin was also used for examining its impact on the expression of mPer1 and mPer2 in vivo.

Biochem/physiol Actions

Cyanocobalamin plays a role in functioning of brain and nervous system. It is also involved in hematopoiesis. Vitamin B12 deficiency leads to megaloblastic anemia. It is also associated with irreversible nervous system breakdown leading to spinal cord degeneration.
Cyanocobalamin refers to a group of chemically-related cobalt containing molecules involved in cell processes such as DNA synthesis, fatty acid synthesis, energy production and regulation. Cyanocobalamin along with other B vitamins thiamine (B1) and pyridoxine (B6) blocks the thermal hyperalgesia in rats with neuropathic pain caused by spinal ganglia compression (CCD) or loose ligation of the sciatic nerve (CCI). It can stimulate the anaerobic biodegradation of chloroform.

General description

Cyanocobalamin, also referred to as Vitamin B12, is a water soluble vitamin.

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
BCCK8133
BCCH0319
BCCD6236
BCCC0930
BCBZ7772

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Anti-nociceptive and anti-inflammatory effects of cyanocobalamin (vitamin B12) against acute and chronic pain and inflammation in mice
Hosseinzadeh H, et al.
Arzneimittelforschung, 62(07), 324-329 (2012)
E Nexo et al.
Clinical chemistry, 46(10), 1643-1649 (2000-10-06)
Transcobalamin is essential for the cellular internalization of cobalamin. Methods to quantify the unsaturated protein are available, but few attempts have been made to develop methods to quantify the sum of unsaturated and cobalamin saturated transcobalamin. gamma-Globulins from two polyclonal
Zheng-Bei Wang et al.
Pain, 114(1-2), 266-277 (2005-03-01)
Neuropathic pain after nerve injury is severe and intractable, and current drugs and nondrug therapies offer substantial pain relief to no more than half of affected patients. The present study investigated the analgesic roles of the B vitamins thiamine (B1)
Krista Kaasik et al.
Nature, 430(6998), 467-471 (2004-07-23)
The circadian clock is the central timing system that controls numerous physiological processes. In mammals, one such process is haem biosynthesis, which the clock controls through regulation of the rate-limiting enzyme aminolevulinate synthase 1 (Alas1). Several members of the core
David Watkins et al.
Biochimie, 95(5), 1019-1022 (2013-02-14)
Since 1975 cells lines from patients with suspected inborn errors of vitamin B12 metabolism have been referred to our laboratory because of elevations of homocysteine, methylmalonic acid, or both. Cultured fibroblasts from patients were subjected to a battery of tests:
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