Methylcobalamin

Methylcobalamin
Methylcobalamin
Systematic (IUPAC) name
carbanide; cobalt(3+);
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat.  ?
Legal status  ?
Routes oral,sublingual,injection.
Identifiers
CAS number 13422-55-4 YesY
ATC code B03BA05
PubChem CID 6436232
UNII BR1SN1JS2W N
ChEMBL CHEMBL1697757 N
Chemical data
Formula C63H91CoN13O14P 
Mol. mass 1344.40 g/mol
 N(what is this?)  (verify)

Methylcobalamin is a cobalamin (MeCbl or MeB12) used in the treatment of peripheral neuropathy, diabetic neuropathy, and as a preliminary treatment for amyotrophic lateral sclerosis. It is a form of vitamin B12 and differs from cyanocobalamin in that the cyanide is replaced by a methyl group.[1] Methylcobalamin features an octahedral cobalt(III) centre.

This vitamer is one of two active coenzymes used by vitamin B12-dependent enzymes and is the specific vitamin B12 form used by 5-methyltetrahydrofolate-homocysteine methyltransferase (MTR), also known as methionine synthase. Methylcobalamin is notable for being one of the few examples in nature of a bona fide organometallic bond, although Ni-CH3 intermediates are proposed for the final step of methanogenesis. In physiological terms, it is equivalent to vitamin B12, e.g. for addressing pathologies arising from a lack of vitamin vitamin B12, such as pernicious anemia.

Contents

Functions

Role in biomethylation

Methylcobalamin plays an important role in the environment. It is produced preferentially by some bacteria. In the environment, it is responsible for the biomethylation of certain heavy metals. For example, the highly toxic methylmercury is produced in this way.[2] In this role, methylcobalamin serves as a source "CH3+". In the Wood-Ljungdahl pathway, methylcobalamin provides the methyl group that couples to carbon monoxide to afford acetyl-CoA.[3]

Small clinical studies

Methylcobalamin has been studied in conjunction with sleep-wake rhythm disorders, where it appears to yield benefits, but at a low or inconsistent level.[4]

Supplementation with megadoses of methylcobalamin has been advocated to protect the cognitive function of patients suffering chronic fatigue syndrome, stroke, depression, Alzheimers disease, and other neurological diseases. The rationale is that methylcobalamin may help to remove brain-damaging levels of the neurotransmitter glutamate. Methylcobalamin has been reported to have been used to reduce neurotoxicity and lower excess glutamate levels, resulting in the reduction of fatigue, stabilisation of mood, improvement of memory, and executive function. However, clinical trials using methylcobalamin have been small and, for the most part, have not been replicated or confirmed.[5]

See also

References

  1. ^ L. R. McDowell, Vitamins in animal and human nutrition, http://books.google.co.uk/books?id=dXOPBMYIPcQC&pg=PA526 
  2. ^ Zenon Schneider, Andrzej Stroiński, Comprehensive B12: Chemistry, Biochemistry, Nutrition, Ecology, Medicine, http://books.google.co.uk/books?id=OBlxCKbYCx8C&pg=PA32 
  3. ^ J. C. Fontecilla-Camps, Patricia Amara, Christine Cavazza, Yvain Nicolet, Anne Volbeda
  4. ^ Double-blind test on the efficacy of methylcobalamin on sleep-wake rhythm disorders
  5. ^ [1]
v · d · eVitamins (A11)
Fat soluble
Tocopherol (Alpha, Beta, Gamma, Delta) · Tocotrienol (Alpha, Beta, Gamma, Delta)  · Tocofersolan
Water soluble
Combinations

M: NUT

cof, enz, met

noco, nuvi, sysi/epon, met

drug(A8/11/12)
v · d · eEnzyme cofactors
Active forms
TPP / ThDP (B1) · FMN, FAD (B2) · NAD+, NADH, NADP+, NADPH (B3) · Coenzyme A (B5) · PLP / P5P (B6) · Biotin (B7) · THFA / H4FA, DHFA / H2FA, MTHF (B9) · AdoCbl, MeCbl (B12) · Ascorbic Acid (C) · Phylloquinone (K1), Menaquinone (K2) · Coenzyme F420
Ca2+ · Cu2+ · Fe2+, Fe3+ · Mg2+ · Mn2+ · Mo · Ni2+ · Se · Zn2+
Base forms
vitamins: see vitamins

M: NUT

cof, enz, met

noco, nuvi, sysi/epon, met

drug(A8/11/12)
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