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MedKoo Cat#: 577244 | Name: Methapyrilene fumarate

Description:

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

Methapyrilene fumarate is a histamine H1 antagonist with sedative action used as a hypnotic and in allergies. It is a hepatocarcinogen in sufficiently high doses, inducing mutations through an indirect genotoxic mechanism; e.g., via an oxidative mechanism or interaction with chromosomal proteins.

Chemical Structure

Methapyrilene fumarate
Methapyrilene fumarate
CAS#33032-12-1

Theoretical Analysis

MedKoo Cat#: 577244

Name: Methapyrilene fumarate

CAS#: 33032-12-1

Chemical Formula: C40H50N6O12S2

Exact Mass: 870.2928

Molecular Weight: 870.99

Elemental Analysis: C, 55.16; H, 5.79; N, 9.65; O, 22.04; S, 7.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Metapyrilene fumarate; Methapyrilene fumarate; Thenylpyramine fumarate
IUPAC/Chemical Name
Pyridine, 2-((2-(dimethylamino)ethyl)-2-thenylamino)-, fumarate (2:3)
InChi Key
OLGIEIJNOQGBSS-VQYXCCSOSA-N
InChi Code
InChI=1S/2C14H19N3S.3C4H4O4/c2*1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14;3*5-3(6)1-2-4(7)8/h2*3-8,11H,9-10,12H2,1-2H3;3*1-2H,(H,5,6)(H,7,8)/b;;3*2-1+
SMILES Code
CN(C)CCN(Cc1cccs1)c2ccccn2.CN(C)CCN(Cc3cccs3)c4ccccn4.OC(=O)\C=C\C(=O)O.OC(=O)\C=C\C(=O)O.OC(=O)\C=C\C(=O)O
Appearance
Solid powder
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 870.99 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
1: Inoue K, Ochi A, Koda A, Wako Y, Kawasako K, Doi T. The 14-day repeated dose liver micronucleus test with methapyrilene hydrochloride using young adult rats. Mutat Res Genet Toxicol Environ Mutagen. 2015 Mar;780-781:123-7. doi: 10.1016/j.mrgentox.2014.04.004. Epub 2014 Apr 24. PubMed PMID: 24768639. 2: Winek CL, Fochtman FW, Trogus WJ Jr, Fusia EP, Shanor SP. Methapyrilene toxicity. Clin Toxicol. 1977;11(3):287-94. PubMed PMID: 913071. 3: Ratra GS, Cottrell S, Powell CJ. Effects of induction and inhibition of cytochromes P450 on the hepatotoxicity of methapyrilene. Toxicol Sci. 1998 Nov;46(1):185-96. PubMed PMID: 9928682. 4: Iype PT, Ray-Chaudhuri R, Lijinsky W, Kelley SP. Inability of methapyrilene to induce sister chromatid exchanges in vitro and in vivo. Cancer Res. 1982 Nov;42(11):4614-8. PubMed PMID: 7127299. 5: Schug M, Stöber R, Heise T, Mielke H, Gundert-Remy U, Godoy P, Reif R, Blaszkewicz M, Ellinger-Ziegelbauer H, Ahr HJ, Selinski S, Günther G, Marchan R, Blaszkewicz M, Sachinidis A, Nüssler A, Oberemm A, Hengstler JG. Pharmacokinetics explain in vivo/in vitro discrepancies of carcinogen-induced gene expression alterations in rat liver and cultivated hepatocytes. Arch Toxicol. 2013 Feb;87(2):337-45. doi: 10.1007/s00204-012-0999-8. Epub 2012 Dec 29. PubMed PMID: 23274394. 6: Priestley CC, Regan S, Kevin Park B, Williams DP. The genotoxic potential of methapyrilene using the alkaline Comet assay in vitro and in vivo. Toxicology. 2011 Dec 18;290(2-3):249-57. doi: 10.1016/j.tox.2011.10.002. Epub 2011 Oct 12. PubMed PMID: 22015589. 7: Ratra GS, Powell CJ, Park BK, Maggs JL, Cottrell S. Methapyrilene hepatotoxicity is associated with increased hepatic glutathione, the formation of glucuronide conjugates, and enterohepatic recirculation. Chem Biol Interact. 2000 Dec 15;129(3):279-95. PubMed PMID: 11137066. 8: Hernandez L, Allen PT, Poirier LA, Lijinsky W. S-adenosylmethionine, S-adenosylhomocysteine and DNA methylation levels in the liver of rats fed methapyrilene and analogs. Carcinogenesis. 1989 Mar;10(3):557-62. PubMed PMID: 2924400. 9: Budroe JD, Shaddock JG, Casciano DA. A study of the potential genotoxicity of methapyrilene and related antihistamines using the hepatocyte/DNA repair assay. Mutat Res. 1984 Feb;135(2):131-7. PubMed PMID: 6141525. 10: Kelly DW, Holder CL, Korfmacher WA, Slikker W Jr. Plasma elimination and urinary excretion of methapyrilene in the rat. Drug Metab Dispos. 1990 Nov-Dec;18(6):1018-24. PubMed PMID: 1981507. 11: Ratra GS, Morgan WA, Mullervy J, Powell CJ, Wright MC. Methapyrilene hepatotoxicity is associated with oxidative stress, mitochondrial disfunction and is prevented by the Ca2+ channel blocker verapamil. Toxicology. 1998 Sep 15;130(2-3):79-93. PubMed PMID: 9865476. 12: Teutsch G, Mahler DL, Brown CR, Forrest WH Jr, James KE, Brown BW. Hypnotic efficacy of diphenhydramine, methapyrilene, and pentobarbital. Clin Pharmacol Ther. 1975 Feb;17(2):195-201. PubMed PMID: 1091393. 13: Kammerer RC, Schmitz DA, Lampe MA, Kloc K. The in vivo metabolism of methapyrilene, a hepatocarcinogen, in the rat. Xenobiotica. 1988 Jul;18(7):869-81. PubMed PMID: 3176524. 14: Auman JT, Chou J, Gerrish K, Huang Q, Jayadev S, Blanchard K, Paules RS. Identification of genes implicated in methapyrilene-induced hepatotoxicity by comparing differential gene expression in target and nontarget tissue. Environ Health Perspect. 2007 Apr;115(4):572-8. Epub 2007 Jan 17. PubMed PMID: 17450226; PubMed Central PMCID: PMC1852695. 15: Casciano DA, Talaska G, Clive D. The potent hepatocarcinogen methapyrilene induces mutations in L5178Y mouse lymphoma cells in the apparent absence of DNA adduct formation. Mutat Res. 1991 Jun;263(2):127-32. PubMed PMID: 2046705. 16: Mergens WJ, Vane FM, Tannenbaum SR, Green L, Skipper PL. In vitro nitrosation of methapyrilene. J Pharm Sci. 1979 Jul;68(7):827-32. PubMed PMID: 458597. 17: Singer SS, Lijinsky W, Kratz LE, Castagnoli N Jr, Rose JE. A comparison of in vivo and in vitro metabolites of the H1-antagonist N,N-dimethyl-N'-2-pyridyl-N'-(2-thienylmethyl)-1,2-ethanediamine (methapyrilene) in the rat. Xenobiotica. 1987 Nov;17(11):1279-91. PubMed PMID: 3433800. 18: Kelly DW, Holder CL, Korfmacher WA, Getek TA, Lay JO Jr, Casciano DA, Shaddock JG, Duhart HM, Slikker W Jr. Metabolism of methapyrilene by Fischer-344 rat and B6C3F1 mouse hepatocytes. Xenobiotica. 1992 Dec;22(12):1367-81. PubMed PMID: 1494883. 19: Oberly TJ, Scheuring JC, Richardson KA, Richardson FC, Garriott ML. The evaluation of methapyrilene for bacterial mutation with metabolic activation by Aroclor-induced, methapyrilene-induced and noninduced rat-liver S9. Mutat Res. 1993 Apr;299(2):77-84. PubMed PMID: 7680426. 20: Ziegler R, Ho B, Castagnoli N Jr. Trapping of metabolically generated electrophilic species with cyanide ion: metabolism of methapyrilene. J Med Chem. 1981 Oct;24(10):1133-8. PubMed PMID: 7328575.