Methylcobalamin - Revision history

Fire: Marked this version for translation

2024-04-07T04:57:15Z

Marked this version for translation

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	{{short description\|Form of vitamin B12}}		{{short description\|Form of vitamin B12}}
	{{Drugbox		{{Drugbox
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	\| image2 = Mecobalamin 3D sticks.png		\| image2 = Mecobalamin 3D sticks.png

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	<!--Clinical data-->		<!--Clinical data-->
	\| tradename = Cobolmin		\| tradename = Cobolmin
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	\| routes_of_administration = [[Oral administration\|By mouth]], sublingual, injection.		\| routes_of_administration = [[Oral administration\|By mouth]], sublingual, injection.

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	\| bioavailability =		\| bioavailability =
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	\| excretion =		\| excretion =

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	<!--Identifiers-->		<!--Identifiers-->
	\| CAS_number_Ref = {{cascite\|correct\|??}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
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	'''Methylcobalamin''' (mecobalamin, MeCbl, or MeB{{sub\|12}}) is a [[cobalamin]], a form of [[vitamin B12\|vitamin B{{sub\|12}}]]. It differs from [[cyanocobalamin]] in that the [[cyanide\|cyano group]] at the cobalt is replaced with a [[methyl group]]. Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals. 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''' (mecobalamin, MeCbl, or MeB{{sub\|12}}) is a [[cobalamin]], a form of [[vitamin B12\|vitamin B{{sub\|12}}]]. It differs from [[cyanocobalamin]] in that the [[cyanide\|cyano group]] at the cobalt is replaced with a [[methyl group]]. Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals. 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]].

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	Methylcobalamin is equivalent physiologically to vitamin B{{sub\|12}}, and can be used to prevent or treat pathology arising from a lack of vitamin B{{sub\|12}} intake ([[vitamin B12 deficiency\|vitamin B<sub>12</sub> deficiency]]).		Methylcobalamin is equivalent physiologically to vitamin B{{sub\|12}}, and can be used to prevent or treat pathology arising from a lack of vitamin B{{sub\|12}} intake ([[vitamin B12 deficiency\|vitamin B<sub>12</sub> deficiency]]).

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

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	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.		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.

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	According to one author, it is important to treat [[vitamin B12\|vitamin B{{sub\|12}}]] deficiency with [[hydroxocobalamin]] or [[cyanocobalamin]] or a combination of [[adenosylcobalamin]] and methylcobalamin, and not methylcobalamin alone.		According to one author, it is important to treat [[vitamin B12\|vitamin B{{sub\|12}}]] deficiency with [[hydroxocobalamin]] or [[cyanocobalamin]] or a combination of [[adenosylcobalamin]] and methylcobalamin, and not methylcobalamin alone.
	__TOC__		__TOC__

	==Production==		==Production== <!--T:9-->
	[[File:B12 methylcobalamin.jpg\|thumb\|left\|300px\|Methylcobalamin physically resembles the other forms of vitamin B<sub>12</sub>, occurring as dark red crystals that freely form cherry-colored transparent solutions in water.]]		[[File:B12 methylcobalamin.jpg\|thumb\|left\|300px\|Methylcobalamin physically resembles the other forms of vitamin B<sub>12</sub>, occurring as dark red crystals that freely form cherry-colored transparent solutions in water.]]

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

	==Functions==		==Functions== <!--T:11-->
	This [[vitamer]], along with [[adenosylcobalamin]], is one of two active coenzymes used by vitamin B{{sub\|12}}-dependent enzymes and is the specific vitamin B{{sub\|12}} form used by [[5-methyltetrahydrofolate-homocysteine methyltransferase]] (MTR), also known as methionine synthase.		This [[vitamer]], along with [[adenosylcobalamin]], is one of two active coenzymes used by vitamin B{{sub\|12}}-dependent enzymes and is the specific vitamin B{{sub\|12}} form used by [[5-methyltetrahydrofolate-homocysteine methyltransferase]] (MTR), also known as methionine synthase.

	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 CO<sub>2</sub>) to afford [[acetyl-CoA]]. Acetyl-CoA is a derivative of acetic acid that is converted to more complex molecules as required by the organism.		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 CO<sub>2</sub>) to afford [[acetyl-CoA]]. Acetyl-CoA is a derivative of acetic acid that is converted to more complex molecules as required by the organism.

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	Methylcobalamin is produced by some [[bacteria]]. It plays an important role in the environment, where it is responsible for the [[biomethylation]] of certain [[heavy metal (chemistry)\|heavy metal]]s. For example, the highly toxic [[methylmercury]] is produced by the action of methylcobalamin. In this role, methylcobalamin serves as a source of "CH<sub>3</sub><sup>+</sup>".		Methylcobalamin is produced by some [[bacteria]]. It plays an important role in the environment, where it is responsible for the [[biomethylation]] of certain [[heavy metal (chemistry)\|heavy metal]]s. For example, the highly toxic [[methylmercury]] is produced by the action of methylcobalamin. In this role, methylcobalamin serves as a source of "CH<sub>3</sub><sup>+</sup>".

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

	== See also ==		== See also == <!--T:14-->
	*[[Cobamamide]]		*[[Cobamamide]]
	*[[Cyanocobalamin]]		*[[Cyanocobalamin]]
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	*[[Cobalamin biosynthesis]]		*[[Cobalamin biosynthesis]]

			<!--T:15-->
	{{Vitamin}}		{{Vitamin}}
	{{Enzyme cofactors}}		{{Enzyme cofactors}}

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	{{二次利用\|date=23 January 2024}}		{{二次利用\|date=23 January 2024}}
	[[Category:B vitamins]]		[[Category:B vitamins]]

Fire at 04:56, 7 April 2024

2024-04-07T04:56:55Z

← Older revision		Revision as of 13:56, 7 April 2024
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	{{short description\|Form of vitamin B12}}		{{short description\|Form of vitamin B12}}
	{{Drugbox		{{Drugbox
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	[[Category:Organocobalt compounds]]		[[Category:Organocobalt compounds]]
	[[Category:Vitamin B12]]		[[Category:Vitamin B12]]
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Fire at 04:53, 7 April 2024

2024-04-07T04:53:49Z

← Older revision		Revision as of 13:53, 7 April 2024
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	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 CO<sub>2</sub>) to afford [[acetyl-CoA]]. Acetyl-CoA is a derivative of acetic acid that is converted to more complex molecules as required by the organism.		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 CO<sub>2</sub>) to afford [[acetyl-CoA]]. Acetyl-CoA is a derivative of acetic acid that is converted to more complex molecules as required by the organism.

	Methylcobalamin is produced by some [[bacteria]].~~{{cn\|date=February 2021}}~~ It plays an important role in the environment, where it is responsible for the [[biomethylation]] of certain [[heavy metal (chemistry)\|heavy metal]]s. For example, the highly toxic [[methylmercury]] is produced by the action of methylcobalamin. In this role, methylcobalamin serves as a source of "CH<sub>3</sub><sup>+</sup>".		Methylcobalamin is produced by some [[bacteria]]. It plays an important role in the environment, where it is responsible for the [[biomethylation]] of certain [[heavy metal (chemistry)\|heavy metal]]s. For example, the highly toxic [[methylmercury]] is produced by the action of methylcobalamin. In this role, methylcobalamin serves as a source of "CH<sub>3</sub><sup>+</sup>".

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

Fire at 04:53, 7 April 2024

2024-04-07T04:53:37Z

← Older revision		Revision as of 13:53, 7 April 2024
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	\| C=63 \| H=91 \| Co=1 \| N=13 \| O=14 \| P=1		\| C=63 \| H=91 \| Co=1 \| N=13 \| O=14 \| P=1
	\|drug_name=\|alt=\|caption=\|type=\|MedlinePlus=\|licence_EU=\|licence_US=}}		\|drug_name=\|alt=\|caption=\|type=\|MedlinePlus=\|licence_EU=\|licence_US=}}
	'''Methylcobalamin''' (mecobalamin, MeCbl, or MeB{{sub\|12}}) is a [[cobalamin]], a form of [[vitamin B12\|vitamin B{{sub\|12}}]]. It differs from [[cyanocobalamin]] in that the [[cyanide\|cyano group]] at the cobalt is replaced with a [[methyl group]]. Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals.~~<ref name="MechB12" />~~ 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''' (mecobalamin, MeCbl, or MeB{{sub\|12}}) is a [[cobalamin]], a form of [[vitamin B12\|vitamin B{{sub\|12}}]]. It differs from [[cyanocobalamin]] in that the [[cyanide\|cyano group]] at the cobalt is replaced with a [[methyl group]]. Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals. 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 B{{sub\|12}}, and can be used to prevent or treat pathology arising from a lack of vitamin B{{sub\|12}} intake ([[vitamin B12 deficiency\|vitamin B<sub>12</sub> deficiency]]).		Methylcobalamin is equivalent physiologically to vitamin B{{sub\|12}}, and can be used to prevent or treat pathology arising from a lack of vitamin B{{sub\|12}} intake ([[vitamin B12 deficiency\|vitamin B<sub>12</sub> deficiency]]).

Fire: Created page with "{{short description|Form of vitamin B12}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 416418921 | IUPAC_name = carbanide; cobalt(3+); | image = Methylcobalamin.png | image2 = Mecobalamin 3D sticks.png | tradename = Cobolmin | Drugs.com = {{drugs.com|international|methylcobalamin}} | pregnancy_AU = | pregnancy_category = | legal_AU =

← Older revision		Revision as of 13:53, 7 April 2024
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	\| C=63 \| H=91 \| Co=1 \| N=13 \| O=14 \| P=1		\| C=63 \| H=91 \| Co=1 \| N=13 \| O=14 \| P=1
	\|drug_name=\|alt=\|caption=\|type=\|MedlinePlus=\|licence_EU=\|licence_US=}}		\|drug_name=\|alt=\|caption=\|type=\|MedlinePlus=\|licence_EU=\|licence_US=}}
	'''Methylcobalamin''' (mecobalamin, MeCbl, or MeB{{sub\|12}}) is a [[cobalamin]], a form of [[vitamin B12\|vitamin B{{sub\|12}}]]. It differs from [[cyanocobalamin]] in that the [[cyanide\|cyano group]] at the cobalt is replaced with a [[methyl group]]. Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals.~~<ref name="MechB12" />~~ 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''' (mecobalamin, MeCbl, or MeB{{sub\|12}}) is a [[cobalamin]], a form of [[vitamin B12\|vitamin B{{sub\|12}}]]. It differs from [[cyanocobalamin]] in that the [[cyanide\|cyano group]] at the cobalt is replaced with a [[methyl group]]. Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals. 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 B{{sub\|12}}, and can be used to prevent or treat pathology arising from a lack of vitamin B{{sub\|12}} intake ([[vitamin B12 deficiency\|vitamin B<sub>12</sub> deficiency]]).		Methylcobalamin is equivalent physiologically to vitamin B{{sub\|12}}, and can be used to prevent or treat pathology arising from a lack of vitamin B{{sub\|12}} intake ([[vitamin B12 deficiency\|vitamin B<sub>12</sub> deficiency]]).