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M9756

Methylcobalamin

Name: Methylcobalamin
Brand: SIGMA

vitamin B₁₂ analog

Synonym(s):

Methyl cobalamine

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About This Item

Empirical Formula (Hill Notation):

C₆₃H₉₁CoN₁₃O₁₄P

CAS Number:

13422-55-4

Molecular Weight:

1344.38

PubChem Substance ID:

329818096

eCl@ss:

34058004

UNSPSC Code:

12352205

NACRES:

NA.79

EC Number:

236-535-3

MDL number:

MFCD00082483

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Properties

Quality Level

100

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

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Akt/mammalian target of rapamycin signaling pathway regulates neurite outgrowth in cerebellar granule neurons stimulated by methylcobalamin.

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

Cobalamin-dependent methionine synthase: the structure of a methylcobalamin-binding fragment and implications for other B12-dependent enzymes.

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

Methylcobalamin: a potential vitamin of pain killer

Zhang M, et al.

Neural Plast. (2013)

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