13422-55-4

Basic information

• Product Name: Mecobalamin
• Synonyms: MECOBALAMIN;MECOBALAMINE;METHYLCOBALAMIN;cobalt-methylcobalamin;cobinamide,cobalt-methylderivative,hydroxide,dihydrogenphosphate(ester),;Methyl-5,6-dimethylbenzimidazolylcobalamin;Vitamin B12;Algobaz
• CAS NO: 13422-55-4
• Molecular Formula: C₆₃H₉₁CoN₁₃O₁₄P
• Molecular Weight: 1344.38
• EINECS: 236-535-3
• Product Categories: PHARMACEUTICALS;Nutritional Supplements;Intermediates & Fine Chemicals;Vitamin B12;Nutrition Research;Vitamins;Vitamin Ingredients;API;Pharmaceutical intermediates
• Mol File: 13422-55-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: >190°C (dec.)
• Appearance: dark red crystalline powder
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Sparingly), Water (Slightly)
• PKA: pK1:7.64(+1) (25°C)
• Water Solubility: Partially soluble in cold water, hot water.
• Stability: Light Sensitie
• CAS DataBase Reference: Mecobalamin(CAS DataBase Reference)
• NIST Chemistry Reference: Mecobalamin(13422-55-4)
• EPA Substance Registry System: Mecobalamin(13422-55-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 2
• RTECS: GG3745000
• Hazardous Substances Data: 13422-55-4(Hazardous Substances Data)

Usage

Description

Mecobalamin, also known as Methylcobalamin, is an analog of vitamin B12 with diverse neurological activities. It is a kind of endogenous coenzyme B12, participating in the one carbon unit cycle and playing an important role in the synthesis of methionine homocysteine methyl transfer reaction process. Mecobalamin is an octahedral cobalt complex consisting of a porphyrin-like, cobalt-centered macroring (called a corrin ring or nucleus). It is a dark red crystalline powder that is soluble in water and fairly stable to heat but decomposes at temperatures above approximately 210 °C without melting.

Uses

Used in Nervous System Applications:
Mecobalamin is used as a treatment for nervous system diseases, relieving pain and numbness, speeding up the relief of pain, improving pain caused by cervical spondylosis, and treating sudden deafness.
Used in Metabolic Processes:
Mecobalamin is used as a coenzyme required in the biosynthesis of methionine, playing a crucial role in the one carbon unit cycle and the methylation of inorganic mercury by anaerobic bacteria in bottom sediments.
Used in Pharmaceutical Industry:
Mecobalamin is used as a vitamin (hematopoietic) and a histamine receptor in Alzheimer research.
Used in Environmental Applications:
Mecobalamin is used as an intermediate in the synthesis of methane, responsible for the methylation of arsenic(III) to methanearsonic acid and then to cacodylic acid through the action of methylcobalamin in anaerobic bacteria in bottom sediments of aquatic systems.

Pharmacological action

Mecobalamin as vitamin B12 derivatives, should be called "methyl vitamin B12" according to the chemical structure of name, the functional groups of methylation can be involved in the biochemical process of methyl transfer activity, promoting to nucleic acid of nerve tissue, the metabolism of protein and fat, , can stimulate the synthesis of lecithin Schwann cells, repairing the damaged myelin, improving nerve conduction velocity; directly into nerve cells, and stimulating axon regeneration of damaged area; stimulating protein synthesis in nerve cells and enhanced synthetic metabolism of axons to prevent axonal degeneration; involved in nucleic acid synthesis, promoted hematopoietic function. The treatment is clinically used in diabetic neuropathy, long-term use of macrovascular complications of diabetes are the curative effect. Mecobalamin is used for peripheral nerve disorders treatment drug, compared with other vitamin B12 preparations, having good transfer on the nervous tissue, through the methyl transfer reaction, can promote nucleic acid, protein lipid metabolism, repairing the damaged nerve tissue. In homocysteine synthetic egg ammonia acid process, it plays a role of coenzyme, especially by deoxyuridine synthesis of thymidine, promoting DNA and RNA synthesis of participation. Also in the experiment of glial cells, the drugs can improve methionine synthase activity and promote the synthesis of myelin lipids lecithin. Improving the nerve tissue metabolism, can promot axis cable and protein synthesis, make the delivery rate of the skeletal protein close to normal, maintain axonal functions. Besides mecobalamin injections can inhibit nerve tissue of abnormal impulse conduction, promoting redl blood cells mature, split, improving anemia. Mecobalamin can be quickly restored due to lack of B12 and reduce the number of rat erythrocytes, hemoglobin, hematocrit value. Used for megaloblastic red blood cell anemia and peripheral nerve disorder due to the lack of vitamin B12. The above information is edited by the lookchem Hanya.

InChI:InChI=1/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/t31?,34-,35-,36-,37+,41+,52?,53?,56?,57+,59-,60+,61+,62+;;/m1../s1

Synthetic route

cyanocobalamin (68-19-9) + trimethyloxosulfonium bromide (25596-24-1) → CH3Cb1 (13422-55-4)

Conditions	Yield
Stage #1: cyanocobalamin With sodium tetrahydroborate; cobalt(II) chloride In water; butanone at 30 - 50℃; for 1.66667 - 2.5h; Stage #2: trimethyloxosulfonium bromide In water; butanone at 15 - 50℃;	85%

cyanocobalamin (68-19-9) + trimethyloxosulfonium bromide (25596-24-1) → CH3Cb1 (13422-55-4) + dimethylsulfide (75-18-3)

Conditions	Yield
With sodium tetrahydroborate; cobalt(II) chloride In water; butanone at 15 - 40℃;

CH3Cb1 (13422-55-4) + cis-diamminediaquaplatinum(II) dinitrate → CoC19H6N4(CH3)(CH3)8(CH2CH2CONH2)3(CH2CONH2)3CH2CH2CONHCH2CH(CH3)O4PC5H6(OH)2OC7H3N2(CH3)2Pt(NH3)2OH2(2+)

Conditions	Yield
In water Kinetics; large excess of Pt-complex incubated at 50, and 80+/-0.5°C with cobalamin;

Upstream product

• 68-19-9 cyanocobalamin 
• 25596-24-1 trimethyloxosulfonium bromide 

Downstream Products

• 18534-66-2 [Co(I)cobalamin] 
• 13422-52-1 aquo[Co(III)cobalamin] 

Related news

Clinical efficacy of intravenous plus oral Mecobalamin (cas 13422-55-4) in patients with peripheral neuropathy using vibration perception thresholds as an indicator of improvement08/01/2019

Mecobalamin has been widely used in the treatment of patients with peripheral neuropathy. Several studies have investigated oral, intravenous (IV), or intramuscular administration of mecobalamin, but no studies on the usefulness of a combination of these routes have been reported. In addition, d...detailed

Effects of Mecobalamin (cas 13422-55-4) injection at acupoints on intractable headaches07/30/2019

The current study attempted to relieve the symptoms of chronic tension-type headache (CTH) and migraine without aura (MWA) by injecting mecobalamin at acupoints (points where acupuncture needles are inserted). The 18 patients, ages 35 to 72 years, in this study had not responded to oral drug the...detailed

Amelioration by Mecobalamin (cas 13422-55-4) of subclinical carpal tunnel syndrome involving unaffected limbs in stroke patients07/29/2019

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Observation on clinical therapeutic efficacy of moxibustion combined with Mecobalamin (cas 13422-55-4) on diabetic perineuropathy and effects on patients' blood homocysteine07/28/2019

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Relevant articles and documents

PROCESS FOR PRODUCING METHYLCOBALAMIN

The present invention provides a novel industrially excellent and ecological process for producing methylcobalamin which is useful as a medicament etc. More specifically, it provides a process for producing methylcobalamin by reducing cyanocobalamin or hy