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MedKoo Cat#: 592256 | Name: Methylhydrazine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methylhydrazine is a hydrazine substituted by one methyl group.

Chemical Structure

Methylhydrazine
Methylhydrazine
CAS#60-34-4

Theoretical Analysis

MedKoo Cat#: 592256

Name: Methylhydrazine

CAS#: 60-34-4

Chemical Formula: CH6N2

Exact Mass: 46.0531

Molecular Weight: 46.07

Elemental Analysis: C, 26.07; H, 13.13; N, 60.80

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Synonym
Methylhydrazine; HSDB 1172; HSDB-1172; HSDB1172
IUPAC/Chemical Name
Hydrazine, methyl-
InChi Key
HDZGCSFEDULWCS-UHFFFAOYSA-N
InChi Code
InChI=1S/CH6N2/c1-3-2/h3H,2H2,1H3
SMILES Code
NNC
Appearance
Liquid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methylhydrazine is a hydrazine substituted by one methyl group.
In vitro activity:
This study reports an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. Reference: J Org Chem. 2021 Feb 5;86(3):2895-2906. https://pubmed.ncbi.nlm.nih.gov/33497222/
In vivo activity:
Aim of the present study was to evaluate the antioxidant efficacy of PQQ-producing probiotic E. coli CFR 16 on DMH (1,2-dimethylhydrazine)-induced systemic oxidative damage and altered neurotransmitter status in rat brain. Blood lipid peroxidation levels exhibited a marked increase while antioxidant enzyme activities of superoxide dismutase, catalase, glucose-6-phosphate dehydrogenase and glutathione peroxidase were found to be reduced in DMH-treated rats. Reference: Curr Microbiol. 2015 May;70(5):690-7. https://pubmed.ncbi.nlm.nih.gov/25586077/

Preparing Stock Solutions

The following data is based on the product molecular weight 46.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ioannou DI, Gioftsidou DK, Tsina VE, Kallitsakis MG, Hatzidimitriou AG, Terzidis MA, Angaridis PA, Lykakis IN. Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex. J Org Chem. 2021 Feb 5;86(3):2895-2906. doi: 10.1021/acs.joc.0c02814. Epub 2021 Jan 26. PMID: 33497222. 2. Pandey S, Singh A, Chaudhari N, Nampoothiri LP, Kumar GN. Protection against 1,2-di-methylhydrazine-induced systemic oxidative stress and altered brain neurotransmitter status by probiotic Escherichia coli CFR 16 secreting pyrroloquinoline quinone. Curr Microbiol. 2015 May;70(5):690-7. doi: 10.1007/s00284-014-0763-9. Epub 2015 Jan 14. PMID: 25586077. 3. Estrada-Flores E, Yáñez Mendoza C. Histology of rat placentas treated with methylhydrazine Ro 4-6467. Bol Estud Med Biol. 1990 Jul-Dec;38(3-4):59-64. PMID: 2103745.
In vitro protocol:
1. Ioannou DI, Gioftsidou DK, Tsina VE, Kallitsakis MG, Hatzidimitriou AG, Terzidis MA, Angaridis PA, Lykakis IN. Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex. J Org Chem. 2021 Feb 5;86(3):2895-2906. doi: 10.1021/acs.joc.0c02814. Epub 2021 Jan 26. PMID: 33497222.
In vivo protocol:
1. Pandey S, Singh A, Chaudhari N, Nampoothiri LP, Kumar GN. Protection against 1,2-di-methylhydrazine-induced systemic oxidative stress and altered brain neurotransmitter status by probiotic Escherichia coli CFR 16 secreting pyrroloquinoline quinone. Curr Microbiol. 2015 May;70(5):690-7. doi: 10.1007/s00284-014-0763-9. Epub 2015 Jan 14. PMID: 25586077. 2. Estrada-Flores E, Yáñez Mendoza C. Histology of rat placentas treated with methylhydrazine Ro 4-6467. Bol Estud Med Biol. 1990 Jul-Dec;38(3-4):59-64. PMID: 2103745.
1: Guyot L, Machon C, Honorat M, Manship B, Bouard C, Vigneron A, Puisieux A, Labarthe E, Jacob G, Dhenain A, Guitton J, Payen L. Metabolomics and cytotoxicity of monomethylhydrazine (MMH) and (E)-1,1,4,4-tetramethyl-2-tetrazene (TMTZ), two liquid propellants. Toxicol In Vitro. 2018 Jun 7;52:70-86. doi: 10.1016/j.tiv.2018.06.005. [Epub ahead of print] PubMed PMID: 29885439. 2: Kallitsakis MG, Tancini PD, Dixit M, Mpourmpakis G, Lykakis IN. Mechanistic Studies on the Michael Addition of Amines and Hydrazines To Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process. J Org Chem. 2018 Feb 2;83(3):1176-1184. doi: 10.1021/acs.joc.7b02637. Epub 2018 Jan 11. PubMed PMID: 29272119. 3: Horowitz KM, Horowitz BZ. Toxicity, Mushroom, Gyromitra. 2017 Dec 21. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2018 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK470580/ PubMed PMID: 29262102. 4: Dhenain A, Darwich C, Sabaté CM, Le DM, Bougrine AJ, Delalu H, Lacôte E, Payen L, Guitton J, Labarthe E, Jacob G. (E)-1,1,4,4-Tetramethyl-2-tetrazene (TMTZ): A Prospective Alternative to Hydrazines in Rocket Propulsion. Chemistry. 2017 Jul 21;23(41):9897-9907. doi: 10.1002/chem.201701468. Epub 2017 Jul 3. PubMed PMID: 28498558. 5: Hu C, Ruan Z, Ding H, Zhou Y, Xiao Q. An Expedient Total Synthesis of Triciribine. Molecules. 2017 Apr 17;22(4). pii: E643. doi: 10.3390/molecules22040643. PubMed PMID: 28420174. 6: Li Q, Yu X, Xu L, Gao JM. Novel method for the producing area identification of Zhongning Goji berries by electronic nose. Food Chem. 2017 Apr 15;221:1113-1119. doi: 10.1016/j.foodchem.2016.11.049. Epub 2016 Nov 10. PubMed PMID: 27979067. 7: Zumeta I, Mendicute-Fierro C, Bustos I, Huertos MA, Rodríguez-Diéguez A, Seco JM, San Sebastian E, Garralda MA. Irida-β-ketoimines Derived from Hydrazines To Afford Metallapyrazoles or N-N Bond Cleavage: A Missing Metallacycle Disclosed by a Theoretical and Experimental Study. Inorg Chem. 2016 Oct 17;55(20):10284-10293. Epub 2016 Sep 30. PubMed PMID: 27689907. 8: Abbas SY, Basyouni WM, El-Bayouki KA, Abdel-Rahman RF. Synthesis and Evaluation of 1-Substituted-Biguanide Derivatives as Anti-Diabetic Agents for Type II Diabetes Insulin Resistant. Drug Res (Stuttg). 2016 Jul;66(7):377-83. doi: 10.1055/s-0042-107349. Epub 2016 May 18. PubMed PMID: 27191826. 9: Mótyán G, Kovács F, Wölfling J, Gyovai A, Zupkó I, Frank É. Microwave-assisted stereoselective approach to novel steroidal ring D-fused 2-pyrazolines and an evaluation of their cell-growth inhibitory effects in vitro. Steroids. 2016 Aug;112:36-46. doi: 10.1016/j.steroids.2016.04.014. Epub 2016 May 3. PubMed PMID: 27154752. 10: Imai T, Harigae R, Moriyama K, Togo H. Preparation of 5-Aryl-2-Alkyltetrazoles with Aromatic Aldehydes, Alkylhydrazine, Di-tert-butyl Azodicarboxylate, and [Bis(trifluoroacetoxy)iodo]benzene. J Org Chem. 2016 May 6;81(9):3975-80. doi: 10.1021/acs.joc.6b00606. Epub 2016 Apr 25. PubMed PMID: 27078200. 11: Gallardo-Fuentes S, Contreras R. Mechanistic insights into the ANRORC-like rearrangement between methylhydrazine and 1,2,4-oxadiazole derivatives. Org Biomol Chem. 2015 Sep 28;13(36):9439-44. doi: 10.1039/c5ob01300c. Epub 2015 Aug 6. PubMed PMID: 26247805. 12: Holzmeier F, Lang M, Fischer I, Hemberger P, Garcia GA, Tang X, Loison JC. Assignment of high-lying bending mode levels in the threshold photoelectron spectrum of NH2: a comparison between pyrolysis and fluorine-atom abstraction radical sources. Phys Chem Chem Phys. 2015 Jul 15;17(29):19507-14. doi: 10.1039/c5cp02964c. PubMed PMID: 26146367. 13: Bonnet CS, Laine S, Buron F, Tircsó G, Pallier A, Helm L, Suzenet F, Tóth É. A Pyridine-Based Ligand with Two Hydrazine Functions for Lanthanide Chelation: Remarkable Kinetic Inertness for a Linear, Bishydrated Complex. Inorg Chem. 2015 Jun 15;54(12):5991-6003. doi: 10.1021/acs.inorgchem.5b00804. Epub 2015 Jun 1. PubMed PMID: 26030671. 14: Moulik S, Kumar KP, Bohra S, Sridhar S. Pervaporation performance of PPO membranes in dehydration of highly hazardous mmh and udmh liquid propellants. J Hazard Mater. 2015 May 15;288:69-79. doi: 10.1016/j.jhazmat.2015.02.020. Epub 2015 Feb 9. PubMed PMID: 25698568. 15: Pandey S, Singh A, Chaudhari N, Nampoothiri LP, Kumar GN. Protection against 1,2-di-methylhydrazine-induced systemic oxidative stress and altered brain neurotransmitter status by probiotic Escherichia coli CFR 16 secreting pyrroloquinoline quinone. Curr Microbiol. 2015 May;70(5):690-7. doi: 10.1007/s00284-014-0763-9. Epub 2015 Jan 14. PubMed PMID: 25586077. 16: Subramanian S, Narayanasastri S, Kami Reddy AR. Single step derivatization with CF3 enone of thiophene at ambient temperature to determine propellant grade hydrazines: a study by GC and GC-MS. Analyst. 2015 Jan 7;140(1):330-9. doi: 10.1039/c4an01648c. PubMed PMID: 25386637. 17: Nakao A, Suzuki H, Ueno H, Iwasaki H, Setsuta T. Discovery of S-adenosyl-L-homocysteine hydrolase inhibitors based on non-adenosine analogs. Bioorg Med Chem Lett. 2014 Sep 1;24(17):4336-40. doi: 10.1016/j.bmcl.2014.06.008. Epub 2014 Jun 21. PubMed PMID: 25022879. 18: Field LD, Li HL, Dalgarno SJ, McIntosh RD. Base-induced dehydrogenation of ruthenium hydrazine complexes. Inorg Chem. 2013 Feb 4;52(3):1570-83. doi: 10.1021/ic302449n. Epub 2013 Jan 22. PubMed PMID: 23339416. 19: Kawai H, Okusu S, Yuan Z, Tokunaga E, Yamano A, Shiro M, Shibata N. Enantioselective synthesis of epoxides having a tetrasubstituted trifluoromethylated carbon center: methylhydrazine-induced aerobic epoxidation of β,β-disubstituted enones. Angew Chem Int Ed Engl. 2013 Feb 18;52(8):2221-5. doi: 10.1002/anie.201209355. Epub 2013 Jan 21. PubMed PMID: 23339133. 20: Wiesweg M, Berchner-Pfannschmidt U, Fandrey J, Petrat F, de Groot H, Kirsch M. Rocket fuel for the quantification of S-nitrosothiols. Highly specific reduction of S-nitrosothiols to thiols by methylhydrazine. Free Radic Res. 2013 Feb;47(2):104-15. doi: 10.3109/10715762.2012.744836. Epub 2012 Dec 5. PubMed PMID: 23181469.