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Methylcobalamin

CAS# 13422-55-4

Methylcobalamin

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Chemical structure

Methylcobalamin

3D structure

Chemical Properties of Methylcobalamin

Cas No. 13422-55-4 SDF Download SDF
PubChem ID 10898559 Appearance Powder
Formula C63H91CoN13O14P+ M.Wt 1344.38
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (74.38 mM)
H2O : 5 mg/mL (3.72 mM; Need ultrasonic)
*"≥" means soluble, but saturation unknown.
Chemical Name carbanide;cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] 1-[3-[(1R,2R,3R,5Z,7S,10Z,12S,13S,15Z,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-24-id-3-yl]propanoylamino]propan-2-yl phosphate
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(=C(C7=NC(=CC8=NC(=C(C4=N5)C)C(C8(C)C)CCC(=O)N)C(C7(C)CC(=O)N)CCC(=O)N)C)[N-]6)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[Co+3]
Standard InChIKey ZFLASALABLFSNM-WYVZQNDMSA-L
Standard 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/t31?,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Methylcobalamin

DescriptionMethylcobalamin a cobalamin, is a form of vitamin B12. Target: Others Methylcobalamin is a cobalamin, a form of vitamin B12. It differs from cyanocobalamin in that the cyanide is replaced by a methyl group. Methylcobalamin features an octahedral cobalt(III) centre. Methylcobalamin 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. Methylcobalamin is equivalent physiologically to vitamin B12, and can be used to prevent or treat pathology arising from a lack of vitamin B12 (vitamin B12 deficiency), such as pernicious anemia. Methylcobalamin is also used in the treatment of peripheral neuropathy, diabetic neuropathy, and as a preliminary treatment for amyotrophic lateral sclerosis. From Wikipedia.

References:
[1]. http://en.wikipedia.org/wiki/Methylcobalamin

Methylcobalamin Dilution Calculator

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Methylcobalamin Molarity Calculator

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Preparing Stock Solutions of Methylcobalamin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.7438 mL 3.7192 mL 7.4384 mL 14.8767 mL 18.5959 mL
5 mM 0.1488 mL 0.7438 mL 1.4877 mL 2.9753 mL 3.7192 mL
10 mM 0.0744 mL 0.3719 mL 0.7438 mL 1.4877 mL 1.8596 mL
50 mM 0.0149 mL 0.0744 mL 0.1488 mL 0.2975 mL 0.3719 mL
100 mM 0.0074 mL 0.0372 mL 0.0744 mL 0.1488 mL 0.186 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Methylcobalamin

Methylcobalamin a cobalamin, is a form of vitamin B12.

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References on Methylcobalamin

Methylcobalamin prevents mutant superoxide dismutase-1-induced motor neuron death in vitro.[Pubmed:27922548]

Neuroreport. 2017 Jan 18;28(2):101-107.

Amyotrophic lateral sclerosis (ALS) is an incurable progressive neurodegenerative disorder that causes motor dysfunction. Treatments and drugs that slow progression of ALS have garnered great interest. In the present study, we show that the vitamin B12 analog Methylcobalamin (MBL) effectively and dose dependently prevented embryonic stem cell-derived motor neuron death induced by cocultivation with astrocytes expressing mutant human superoxide dismutase-1 (G93A). Moreover, cotreatment of MBL with a conventional ALS drug, riluzole, further enhanced survival of motor neurons in this in-vitro ALS model. Our results show the potential use of MBL as a treatment for ALS and suggest a possible combination therapy strategy with other types of approved ALS drugs.

Acupuncture combined with methylcobalamin for the treatment of chemotherapy-induced peripheral neuropathy in patients with multiple myeloma.[Pubmed:28068938]

BMC Cancer. 2017 Jan 9;17(1):40.

BACKGROUND: Chemotherapy-induced peripheral neuropathy (CIPN) seriously affects the quality of life of patients with multiple myeloma (MM) as well as the response rate to chemotherapy. Acupuncture has a potential role in the treatment of CIPN, but at present there have been no randomized clinical research studies to analyze the effectiveness of acupuncture for the treatment of CIPN, particularly in MM patients. METHODS: The MM patients (104 individuals) who met the inclusion criteria were randomly assigned into a solely Methylcobalamin therapy group (500 mug intramuscular Methylcobalamin injections every other day for 20 days; ten injections) followed by 2 months of 500 mug oral Methylcobalamin administration, three times per day) and an acupuncture combined with Methylcobalamin (Met + Acu) group (Methylcobalamin used the same way as above accompanied by three cycles of acupuncture). Of the patients, 98 out of 104 completed the treatment and follow-ups. There were 49 patients in each group. The evaluating parameters included the visual analogue scale (VAS) pain score, Functional Assessment of Cancer Therapy/Gynecologic Oncology Group-Neurotoxicity (Fact/GOG-Ntx) questionnaire scores, and electromyographic (EMG) nerve conduction velocity (NCV) determinations. We evaluated the changes of the parameters in each group before and after the therapies and made a comparison between the two groups. RESULTS: After 84 days (three cycles) of therapy, the pain was significantly alleviated in both groups, with a significantly higher decrease in the acupuncture treated group (P < 0.01). The patients' daily activity evaluated by Fact/GOG-Ntx questionnaires significantly improved in the Met + Acu group (P < 0.001). The NCV in the Met + Acu group improved significantly while amelioration in the control group was not observed. CONCLUSIONS: The present study suggests that acupuncture combined with Methylcobalamin in the treatment of CIPN showed a better outcome than Methylcobalamin administration alone. TRIAL REGISTRATION: China Clinical Trials Register (registration no. ChiCTR-INR-16009079 , registration date August 24, 2016).

Electrospun nanofiber sheets incorporating methylcobalamin promote nerve regeneration and functional recovery in a rat sciatic nerve crush injury model.[Pubmed:28179161]

Acta Biomater. 2017 Apr 15;53:250-259.

Peripheral nerve injury is one of common traumas. Although injured peripheral nerves have the capacity to regenerate, axon regeneration proceeds slowly and functional outcomes are often poor. Pharmacological enhancement of regeneration can play an important role in increasing functional recovery. In this study, we developed a novel electrospun nanofiber sheet incorporating Methylcobalamin (MeCbl), one of the active forms of vitamin B12 homologues, to deliver it enough locally to the peripheral nerve injury site. We evaluated whether local administration of MeCbl at the nerve injury site was effective in promoting nerve regeneration. Electrospun nanofiber sheets gradually released MeCbl for at least 8weeks when tested in vitro. There was no adverse effect of nanofiber sheets on function in vivo of the peripheral nervous system. Local implantation of nanofiber sheets incorporating MeCbl contributed to the recovery of the motor and sensory function, the recovery of nerve conduction velocity, and the promotion of myelination after sciatic nerve injury, without affecting plasma concentration of MeCbl. STATEMENT OF SIGNIFICANCE: Methylcobalamin (MeCbl) is a vitamin B12 analog and we previously reported its effectiveness in axonal outgrowth of neurons and differentiation of Schwann cells both in vitro and in vivo. Here we estimated the effect of local administered MeCbl with an electrospun nanofiber sheet on peripheral nerve injury. Local administration of MeCbl promoted functional recovery in a rat sciatic nerve crush injury model. These sheets are useful for nerve injury in continuity differently from artificial nerve conduits, which are useful only for nerve defects. We believe that the findings of this study are relevant to the scope of your journal and will be of interest to its readership.

The Effect of Pregabalin and Methylcobalamin Combination on the Chronic Postthoracotomy Pain Syndrome.[Pubmed:27916242]

Ann Thorac Surg. 2017 Apr;103(4):1109-1113.

BACKGROUND: Chronic postthoracotomy pain (CPTP) consists of different types of pain. Some characteristics of CPTP are the same as those of recognized neuropathic pain syndromes. We aimed to determine the safety and efficacy of pregabalin and Methylcobalamin combination (PG-B12) in comparison with diclofenac potassium (DP) in patients with CPTP. METHODS: One hundred consecutive patients with CPTP after posterolateral/lateral thoracotomy were prospectively randomly assigned and evaluated. Fifty patients were given PG-B12 and another 50 patients were given DP treatment. Visual Analogue Scale (VAS) and the Leeds Assessment of Neuropathic Symptoms and Signs (LANSS) scorings were performed previous to the treatment (day 0) and on the 15th, 30th, 60th, and 90th days. Adverse events were questioned. RESULTS: The mean ages were 58.7 +/- 12.2 and 54.6 +/- 14.5 years, and the mean durations of pain were 4.01 +/- 1.04 and 3.8 +/- 1.02 months, respectively. The number of patients with a VAS score less than 5 at the latest follow-up (VAS90 < 5) was 44 (88%) and 18 (36%) in the PG-B12 and DP groups, respectively (p < 0.05). Forty-four patients (88%) in the PG-B12 group and 16 patients (32%) in the DP group had a LANSS score less than 12 at the latest follow-up (p < 0.05). Minor adverse events that did not mandate discontinuation of the treatment were observed in 14 patients (28%) in the PG-B12 group and 2 patients (4%) in the DP group. CONCLUSIONS: PB-B12 is safe and effective in the treatment of CPTP with minimal side effects and a high patient compliance. These results should be supported by multidisciplinary studies with larger sample sizes and longer follow-ups.

Description

Methylcobalamin (CH3-B12), a cobalamin, is a form of vitamin B12.

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