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M9756

Sigma-Aldrich

Methylcobalamin

vitamin B12 analog

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Synonym(s):
Methyl cobalamine
Empirical Formula (Hill Notation):
C63H91CoN13O14P
CAS Number:
Molecular Weight:
1344.38
EC Number:
MDL number:
eCl@ss:
34058004
PubChem Substance ID:
NACRES:
NA.79

biological source

synthetic (organic)

Assay

≥97%

form

powder

technique(s)

HPLC: suitable

color

red to very dark red

storage temp.

−20°C

SMILES string

C[Co+]N1C2=C(C)C3=NC(=CC4=NC([C@@H](CCC(N)=O)C4(C)C)=C(C)C5=N[C@H]([C@H](CC(N)=O)[C@@]5(C)CCC(=O)NCC(C)OP([O-])(=O)O[C@H]6[C@@H](O)[C@H](O[C@@H]6CO)n7cnc8cc(C)c(C)cc78)[C@@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O)[C@@H](CCC(N)=O)[C@]3(C)CC(N)=O

InChI

1S/C62H90N13O14P.CH3.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;;/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);1H3;/q;;+2/p-2/t31?,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1

InChI key

JEWJRMKHSMTXPP-WYVZQNDMSA-L

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1 of 4

This Item
H8017C3607SMB00294
Methylcobalamin vitamin B12 analog

Sigma-Aldrich

M9756

Methylcobalamin

Cyanocobalamin meets USP testing specifications

Sigma-Aldrich

C3607

Cyanocobalamin

assay

≥97%

assay

≥95% (HPLC)

assay

96.0-102.0% dry basis

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

powder

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

-

technique(s)

HPLC: suitable

color

red to very dark red

color

red to brown

color

dark red

color

white to off-white

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

General description

Methylcobalamin (MeCbl) is an analog of vitamin B12 (cobalamin). It differs from cobalamin by containing a methyl group. The physiologically active form of vitamin B12 include methylcobalamin and adenosylcobalamin.

Application

Methylcobalamin has been used for the preparation of standard solution to serum vitamin B12 in automated competitive protein binding (CPB) assays.

Biochem/physiol Actions

Methylcobalamin (MeCbl) is a coenzyme for methionine synthase. Methionine synthase is an enzyme, that is involved in the conversion of homocysteine to methionine in the methylation cycle. It plays a role in nervous disorder improvement, carpal tunnel syndrome and bell′s palsy.
Vitamin B12 analog that is a less effective inhibitor of nitric oxide synthase (NOS) than other corrins/cobalamin derivatives.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Methylcobalamin: a potential vitamin of pain killer
Zhang M, et al.
Neural Plast. (2013)
Kiyoshi Okada et al.
Neuroscience letters, 495(3), 201-204 (2011-04-05)
Methylcobalamin (MeCbl), a vitamin B12 analog, promotes neurite outgrowth by activating Akt in neurons. However, Akt is involved in many cellular functions, and the downstream signal of Akt that promotes neurite outgrowth in neurons in the presence of MeCbl remains
C L Drennan et al.
Current opinion in structural biology, 4(6), 919-929 (1994-12-01)
Cobalamin-dependent methionine synthase is a large enzyme composed of structurally and functionally distinct regions. Recent studies have begun to define the roles of several regions of the protein. In particular, the structure of a 27 kDa cobalamin-binding fragment of the
John David Spence
Clinical chemistry and laboratory medicine, 51(3), 633-637 (2013-03-02)
Therapy to lower homocysteine with B vitamins does reduce the risk of stroke, if not myocardial infarction. The apparent lack of efficacy of vitamin therapy in most of the large clinical trials was probably determined by the failure to take
Kenneth M Prentice et al.
mAbs, 5(6), 974-981 (2013-08-09)
Process control of protein therapeutic manufacturing is central to ensuring the product is both safe and efficacious for patients. In this work, we investigate the cause of pink color variability in development lots of monoclonal antibody (mAb) and Fc-fusion proteins.

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