Dihydromethysticin | CAS#19902-91-1 | antinociceptive

MedKoo Cat#: 585106 | Name: Dihydromethysticin

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Description:

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

Dihydromethysticin is a kavalactone originally isolated from P. methysticum (kava-kava) that has diverse biological activities, including efflux transporter inhibitory, antinociceptive, and neuroprotective properties.

Chemical Structure

Dihydromethysticin

CAS# 19902-91-1

Theoretical Analysis

MedKoo Cat#: 585106

Name: Dihydromethysticin

CAS#: 19902-91-1

Chemical Formula: C15H16O5

Exact Mass: 276.0998

Molecular Weight: 276.29

Elemental Analysis: C, 65.21; H, 5.84; O, 28.95

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Synonym

Dihydromethysticin; (+)-Dihydromethysticin; 7,8-Dihydromethysticin; Methysticin, 7,8-dihydro-; DHM; NSC 112159; NSC112159; NSC-112159

IUPAC/Chemical Name

(6S)-6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one

InChi Key

RSIWXFIBHXYNFM-NSHDSACASA-N

InChi Code

InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3/t11-/m0/s1

SMILES Code

O=C1C=C(OC)C[C@H](CCC2=CC=C(OCO3)C3=C2)O1

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

>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:

Dihydromethysticin is one of the six major kavalactones found in the kava plant; has marked activity on the induction of CYP3A23.

In vitro activity:

MG-63 cells were treated with different concentrations (0, 2.5, 5, 25, 75 and 100 µM) of dihydromethysticin for 12, 24, and 48 hours and cell viability was evaluated using an MTT assay. Figure 1 shows the dose-dependent as well as time dependent growth inhibitory effects of dihydromethysticin on the cell viability of MG-63 osteosarcoma cells. Reference: Int J Clin Exp Pathol. 2015 May 1;8(5):4356-66. https://pubmed.ncbi.nlm.nih.gov/26191127/

In vivo activity:

As shown in Fig. 1A, the orally dosed DHM (dihydromethysticin) demonstrated a clear dose-response relationship in blocking NNK-induced lung tumorigenesis in A/J mice. Specifically DHM at a dose of 2.0 mg/mouse decreased NNK-induced adenoma multiplicity by 98.9%. DHM at 0.8 mg/mouse reduced adenoma multiplicity by 93.3%. Even at 0.4 and 0.2 mg per dose, DHM demonstrated significant effects in reducing adenoma formation (49.8% and 42.0% reduction respectively). Reference: Chem Res Toxicol. 2020 Jul 20;33(7):1980-1988. https://pubmed.ncbi.nlm.nih.gov/32476407/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	100.0	361.94

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 276.29 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

Formulation protocol:

1. Dai JQ, Huang YG, He AN. Dihydromethysticin kavalactone induces apoptosis in osteosarcoma cells through modulation of PI3K/Akt pathway, disruption of mitochondrial membrane potential and inducing cell cycle arrest. Int J Clin Exp Pathol. 2015 May 1;8(5):4356-66. PMID: 26191127; PMCID: PMC4502999. 2. Hu Q, Corral P, Narayanapillai SC, Leitzman P, Upadhyaya P, O'Sullivan MG, Hecht SS, Lu J, Xing C. Oral Dosing of Dihydromethysticin Ahead of Tobacco Carcinogen NNK Effectively Prevents Lung Tumorigenesis in A/J Mice. Chem Res Toxicol. 2020 Jul 20;33(7):1980-1988. doi: 10.1021/acs.chemrestox.0c00161. Epub 2020 Jun 11. PMID: 32476407; PMCID: PMC8178726. 3. Narayanapillai SC, Lin SH, Leitzman P, Upadhyaya P, Baglole CJ, Xing C. Dihydromethysticin (DHM) Blocks Tobacco Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-Induced O6-Methylguanine in a Manner Independent of the Aryl Hydrocarbon Receptor (AhR) Pathway in C57BL/6 Female Mice. Chem Res Toxicol. 2016 Nov 21;29(11):1828-1834. doi: 10.1021/acs.chemrestox.6b00203. Epub 2016 Oct 21. PMID: 27728767; PMCID: PMC6532060.

In vitro protocol:

In vivo protocol:

1. Hu Q, Corral P, Narayanapillai SC, Leitzman P, Upadhyaya P, O'Sullivan MG, Hecht SS, Lu J, Xing C. Oral Dosing of Dihydromethysticin Ahead of Tobacco Carcinogen NNK Effectively Prevents Lung Tumorigenesis in A/J Mice. Chem Res Toxicol. 2020 Jul 20;33(7):1980-1988. doi: 10.1021/acs.chemrestox.0c00161. Epub 2020 Jun 11. PMID: 32476407; PMCID: PMC8178726. 2. Narayanapillai SC, Lin SH, Leitzman P, Upadhyaya P, Baglole CJ, Xing C. Dihydromethysticin (DHM) Blocks Tobacco Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-Induced O6-Methylguanine in a Manner Independent of the Aryl Hydrocarbon Receptor (AhR) Pathway in C57BL/6 Female Mice. Chem Res Toxicol. 2016 Nov 21;29(11):1828-1834. doi: 10.1021/acs.chemrestox.6b00203. Epub 2016 Oct 21. PMID: 27728767; PMCID: PMC6532060.

1. Jamieson, D.D., and Duffield, P.H. The antinociceptive actions of kava components in mice. Clin. Exp. Pharmacol. Physiol. 17(7), 495-507 (1990). 2. Backhauβ, C., and Krieglstein, J. Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodent. Eur. J. Pharmacol. 215(2-3), 265-269 (1992). 3. Weiss, J., Sauer, A., Frank, A., et al. Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro. Drug Metab. Dispos. 33(11), 1580-1583 (2005).