Related CAS #
914-00-1 (free base); 41672-87-1 (trolamine); 3963-95-9 (HCl)
Synonym
Methacycline Free Base; GS2876; GS-2876; GS 2876; HSDB3118; HSDB-3118; HSDB 3118
IUPAC/Chemical Name
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-
InChi Key
MHIGBKBJSQVXNH-IWVLMIASSA-N
InChi Code
InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1
SMILES Code
O=C(C(C1=O)=C(O)[C@@H](N(C)C)[C@]2([H])[C@@H](O)[C@]3([H])C(C4=C(C(C3=C(O)[C@@]21O)=O)C(O)=CC=C4)=C)N
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
442.42
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.
| 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 |
1: Amigoni L, Airoldi C, Natalello A, Romeo M, Diomede L, Tortora P, Regonesi ME. Methacycline displays a strong efficacy in reducing toxicity in a SCA3 Caenorhabditis elegans model. Biochim Biophys Acta Gen Subj. 2019 Feb;1863(2):279-290. doi: 10.1016/j.bbagen.2018.10.008. Epub 2018 Oct 27. PMID: 30420336.
2: Xi Y, Tan K, Brumwell AN, Chen SC, Kim YH, Kim TJ, Wei Y, Chapman HA. Inhibition of epithelial-to-mesenchymal transition and pulmonary fibrosis by methacycline. Am J Respir Cell Mol Biol. 2014 Jan;50(1):51-60. doi: 10.1165/rcmb.2013-0099OC. PMID: 23944988; PMCID: PMC3930932.
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5: Yung HW, Colleoni F, Dommett E, Cindrova-Davies T, Kingdom J, Murray AJ, Burton GJ. Noncanonical mitochondrial unfolded protein response impairs placental oxidative phosphorylation in early-onset preeclampsia. Proc Natl Acad Sci U S A. 2019 Sep 3;116(36):18109-18118. doi: 10.1073/pnas.1907548116. Epub 2019 Aug 22. PMID: 31439814; PMCID: PMC6731647.
6: Frost P, Weinstein GD, Gomez EC. Methacycline and demeclocycline in relation to sunlight. JAMA. 1971 Apr 12;216(2):326-9. PMID: 5107921.
7: Minassian M, Dargent D, Amouroux R, Tairraz JP, Pelissier B. La méthylènecycline en gynécologie [Methacycline in gynecology]. Lyon Med. 1967 Dec 17;218(51):1643-5. French. PMID: 5622040.
8: Ossido G, Sfondrini G, Zampetti G, Corvi G. La metaciclina in odontoiatria [Methacycline in dentistry]. Riv Ital Stomatol. 1966 Jun;21(6):605-12. Italian. PMID: 5224265.
9: Chodosh S, Baigelman W, Medici TC. Methacycline compared with ampicillin in acute bacterial exacerbations of chronic bronchitis. A double-blind crossover study. Chest. 1976 May;69(5):587-92. doi: 10.1378/chest.69.5.587. PMID: 773601.
10: Hansson LI, Stenstrom A, Thorngren KG. Skeletal deposition and toxicity of methacycline. Nature. 1968 Aug 10;219(5154):624-5. doi: 10.1038/219624a0. PMID: 5665716.
