Methapyrilene HCl
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Hodoodo CAT#: H341569

CAS#: 135-23-9

Description: Methapyrilene is a histamine H1 receptor antagonist (Ki = 4.5 nM) and non-genotoxic carcinogen. Dietary administration of methapyrilene (0.1%) induces liver tumors in rats, with greater than 50% of rats incurring distant metastases. It decreases the acetylation of histone 3 lysine 9 (H3K9) and H3K56, as well as the di- and trimethylation of H3K4 and H4K20, respectively, in rat liver when administered at 40 mg/kg per day for six weeks. Methapyrilene also increases 4-hydroxy nonenal (4-NHE) protein adducts in rat liver. Formulations containing methapyrilene were previously used as sleep aids.

Chemical Structure

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Methapyrilene HCl
CAS# 135-23-9
Instruction

Theoretical Analysis

Hodoodo Cat#: H341569
Name: Methapyrilene HCl
CAS#: 135-23-9
Chemical Formula: C14H20ClN3S
Exact Mass: 297.11
Molecular Weight: 297.845
Elemental Analysis: C, 56.46; H, 6.77; Cl, 11.90; N, 14.11; S, 10.76

Price and Availability

Size Price Availability Quantity
100mg USD 285 2 Weeks
250mg USD 550 2 Weeks
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Synonym: Methapyrilene hydrochloride; Methapyrilene HCl; Coryzol; Teralin;

IUPAC/Chemical Name: 1,2-Ethanediamine, N,N-dimethyl-N'-2-pyridinyl-N'-(2-thienylmethyl)-, monohydrochloride

InChi Key: BONORRGKLJBGRV-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H19N3S.ClH/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14;/h3-8,11H,9-10,12H2,1-2H3;1H

SMILES Code: CN(C)CCN(C1=NC=CC=C1)CC2=CC=CS2.[H]Cl

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: Soluble in DMSO

Shelf Life: >2 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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 297.85 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:
In vitro protocol:
In vivo protocol:

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1: Kindrat I, Dreval K, Shpyleva S, Tryndyak V, de Conti A, Mudalige TK, Chen T, Erstenyuk AM, Beland FA, Pogribny IP. Effect of methapyrilene hydrochloride on hepatic intracellular iron metabolism in vivo and in vitro. Toxicol Lett. 2017 Nov 5;281:65-73. doi: 10.1016/j.toxlet.2017.09.011. Epub 2017 Sep 19. PubMed PMID: 28935588.

2: 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.

3: Doktorova TY, Ates G, Vinken M, Vanhaecke T, Rogiers V. Way forward in case of a false positive in vitro genotoxicity result for a cosmetic substance? Toxicol In Vitro. 2014 Feb;28(1):54-9. doi: 10.1016/j.tiv.2013.09.022. Epub 2013 Oct 2. PubMed PMID: 24095862.

4: Yafune A, Taniai E, Morita R, Akane H, Kimura M, Mitsumori K, Shibutani M. Immunohistochemical cellular distribution of proteins related to M phase regulation in early proliferative lesions induced by tumor promotion in rat two-stage carcinogenesis models. Exp Toxicol Pathol. 2014 Jan;66(1):1-11. doi: 10.1016/j.etp.2013.07.001. Epub 2013 Jul 23. PubMed PMID: 23890812.

5: Taniai E, Yafune A, Kimura M, Morita R, Nakane F, Suzuki K, Mitsumori K, Shibutani M. Fluctuations in cell proliferation, apoptosis, and cell cycle regulation at the early stage of tumor promotion in rat two-stage carcinogenesis models. J Toxicol Sci. 2012;37(6):1113-26. PubMed PMID: 23208427.

6: Doktorova TY, Ellinger-Ziegelbauer H, Vinken M, Vanhaecke T, van Delft J, Kleinjans J, Ahr HJ, Rogiers V. Comparison of hepatocarcinogen-induced gene expression profiles in conventional primary rat hepatocytes with in vivo rat liver. Arch Toxicol. 2012 Sep;86(9):1399-411. doi: 10.1007/s00204-012-0847-x. Epub 2012 Apr 8. PubMed PMID: 22484513.

7: Sakai A, Sasaki K, Hayashi K, Muramatsu D, Arai S, Endou N, Kuroda S, Poth A, Bohnenberger S, Kunkelmann T, Asakura M, Hirose H, Ishii N, Mizuhashi F, Kasamoto S, Nagai M, Pant K, Bruce SW, Sly JE, Yamazaki S, Umeda M, Tanaka N. An international validation study of a Bhas 42 cell transformation assay for the prediction of chemical carcinogenicity. Mutat Res. 2011 Oct 9;725(1-2):57-77. doi: 10.1016/j.mrgentox.2011.07.006. Epub 2011 Jul 27. PubMed PMID: 21801851.

8: Wu G, Vashishtha SC, Erve JC. Characterization of glutathione conjugates of duloxetine by mass spectrometry and evaluation of in silico approaches to rationalize the site of conjugation for thiophene containing drugs. Chem Res Toxicol. 2010 Aug 16;23(8):1393-404. doi: 10.1021/tx100141d. PubMed PMID: 20669986.

9: NTP Hepatotoxicity Studies of the Liver Carcinogen Methapyrilene Hydrochloride (CAS No. 135-23-9) Administered in Feed to Male F344/N Rats. Toxic Rep Ser. 2000 Feb;46:1-C7. PubMed PMID: 11986676.

10: Horn DM, Jordan WH, Holloway DC, Smith WC, Richardson FC. Dose-dependent induction of GST-P+ staining foci by the rat hepatocarcinogen methapyrilene in the medium-term bioassay. Fundam Appl Toxicol. 1996 Feb;29(2):194-7. PubMed PMID: 8742315.

11: Greenman DL, Sheldon W, Schieferstein G, Allen R, Allaben WT. Triprolidine: 104-week feeding study in rats. Fundam Appl Toxicol. 1995 Sep;27(2):223-31. PubMed PMID: 8529817.

12: Lee HK, Kim YH, Roh JK. Clastogenicity of methapyrilene hydrochloride in cultured Chinese hamster cells. Mutat Res. 1994 Dec;341(2):77-82. Erratum in: Mutat Res 1995 Apr;342(3-4):197. PubMed PMID: 7990858.

13: Lijinsky W, Kovatch RM, Thomas BJ. The carcinogenic effect of methapyrilene combined with nitrosodiethylamine given to rats in low doses. Carcinogenesis. 1992 Jul;13(7):1293-7. PubMed PMID: 1638702.

14: 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.

15: Glauert HP, Pitot HC. Effect of the antihistamine, methapyrilene, as an initiator of hepatocarcinogenesis in female rats. Cancer Lett. 1989 Aug;46(3):189-94. PubMed PMID: 2569926.

16: 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.

17: Lay JO Jr, Getek TA, Kelly DW, Slikker W Jr, Korfmacher WA. Fast-atom bombardment and thermospray mass spectrometry for the characterization of two glucuronide metabolites of methapyrilene. Rapid Commun Mass Spectrom. 1989 Mar;3(3):72-5. PubMed PMID: 2520227.

18: Casciano DA, Shaddock JG, Talaska G. The potent hepatocarcinogen methapyrilene does not form DNA adducts in livers of Fischer 344 rats. Mutat Res. 1988 Jul;208(3-4):129-35. PubMed PMID: 3398863.

19: Jones CA, Huberman E, Callaham MF, Tu A, Halloween W, Pallota S, Sivak A, Lubet RA, Avery MD, Kouri RE, Spalding J, Tennant RW. An interlaboratory evaluation of the Syrian hamster embryo cell transformation assay using eighteen coded chemicals. Toxicol In Vitro. 1988;2(2):103-16. PubMed PMID: 20702344.

20: Perera MI, Katyal SL, Shinozuka H. Choline deficient diet enhances the initiating and promoting effects of methapyrilene hydrochloride in rat liver as assayed by the induction of gamma-glutamyltranspeptidase-positive hepatocyte foci. Br J Cancer. 1987 Dec;56(6):774-8. PubMed PMID: 2893639; PubMed Central PMCID: PMC2002423.