Methylcobalamin

Methylcobalamin
Clinical data
Trade names	Cobolmin
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth, sublingual, injection.
ATC code	B03BA05 (WHO) ;
Legal status
Legal status	US: OTC;
Identifiers
	IUPAC name carbanide; cobalt(3+);;
CAS Number	13422-55-4 ;
PubChem CID	6436232;
ChemSpider	29368587;
UNII	BR1SN1JS2W;
ChEMBL	ChEMBL1697757 ;
CompTox Dashboard (EPA)	DTXSID5048631 ;
ECHA InfoCard	100.033.200
Chemical and physical data
Formula	C63H91CoN13O14P
Molar mass	1344.405 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [CH3-].CC1=CC2=C(C=C1C)N(C=N2)C3C(C(C(O3)CO)OP(=O)([O-])OC(C)CNC(=O)CCC4(C(C5C6(C(C(C(=N6)C(=C7C(C(C(=N7)C=C8C(C(C(=N8)C(=C4[N-]5)C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[Co+3];
	InChI 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;-1;+3/p-2; Key:ZFLASALABLFSNM-UHFFFAOYSA-L;
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Methylcobalamin (mecobalamin, MeCbl, or MeB₁₂) is a cobalamin, a form of vitamin B₁₂. It differs from cyanocobalamin in that the cyano group at the cobalt is replaced with a methyl group.^[1] Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals.^[2] From the perspective of coordination chemistry, methylcobalamin is notable as a rare example of a compound that contains metal–alkyl bonds. Nickel–methyl intermediates have been proposed for the final step of methanogenesis.

Methylcobalamin is equivalent physiologically to vitamin B₁₂,^[3] and can be used to prevent or treat pathology arising from a lack of vitamin B₁₂ intake (vitamin B₁₂ deficiency).

Methylcobalamin is also used in the treatment of peripheral neuropathy, diabetic neuropathy, and as a preliminary treatment for amyotrophic lateral sclerosis.^[4]

Methylcobalamin that is ingested is not used directly as a cofactor, but is first converted by MMACHC into cob(II)alamin. Cob(II)alamin is then later converted into the other two forms, adenosylcobalamin and methylcobalamin for use as cofactors. That is, methylcobalamin is first dealkylated and then regenerated.^[5]^[6]^[7]

According to one author, it is important to treat vitamin B₁₂ deficiency with hydroxocobalamin or cyanocobalamin or a combination of adenosylcobalamin and methylcobalamin, and not methylcobalamin alone.^[8]

Production

Methylcobalamin can be produced in the laboratory by reducing cyanocobalamin with sodium borohydride in alkaline solution, followed by the addition of methyl iodide.^[2]

Functions

This vitamer, along with adenosylcobalamin, 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.^{[citation needed]}

Methylcobalamin participates in the Wood-Ljungdahl pathway, which is a pathway by which some organisms utilize carbon dioxide as their source of organic compounds. In this pathway, methylcobalamin provides the methyl group that couples to carbon monoxide (derived from CO₂) to afford acetyl-CoA. Acetyl-CoA is a derivative of acetic acid that is converted to more complex molecules as required by the organism.^[9]

Methylcobalamin is produced by some bacteria.^{[citation needed]} It plays an important role in the environment, where it is responsible for the biomethylation of certain heavy metals. For example, the highly toxic methylmercury is produced by the action of methylcobalamin.^[10] In this role, methylcobalamin serves as a source of "CH₃⁺".

A lack of cobalamin can lead to megaloblastic anemia and subacute combined degeneration of the spinal cord.^[11]