Dihydroquinine | CAS#522-66-7 | Biochemical

MedKoo Cat#: 150155 | Name: Dihydroquinine

Description:

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

Hydroquinine is an organic compound that is closely related to quinine-derivative drugs and contains anti-malarial and anti-arrhythmia activities. Hydroquinine is used in skin lightening creams and lotions because it is an effective bleaching agent, slowing the production of the tyrosinase enzyme and reducing the amount of melanin formed.

Chemical Structure

Dihydroquinine

CAS#522-66-7

Theoretical Analysis

MedKoo Cat#: 150155

Name: Dihydroquinine

CAS#: 522-66-7

Chemical Formula: C20H26N2O2

Exact Mass: 326.1990

Molecular Weight: 326.44

Elemental Analysis: C, 73.59; H, 8.03; N, 8.58; O, 9.80

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Hydroquinine; Dihydroquinine; (-)-Dihydroquinine;

IUPAC/Chemical Name

(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

InChi Key

LJOQGZACKSYWCH-WZBLMQSHSA-N

InChi Code

1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1

SMILES Code

O[C@@H]([C@H]1N(CC2)C[C@H](CC)[C@]2([H])C1)C3=CC=NC4=CC=C(OC)C=C34

Appearance

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 326.44 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: Rattanachak N, Weawsiangsang S, Jongjitvimol T, Baldock RA, Jongjitwimol J. Hydroquinine Possesses Antibacterial Activity, and at Half the MIC, Induces the Overexpression of RND-Type Efflux Pumps Using Multiplex Digital PCR in Pseudomonas aeruginosa. Trop Med Infect Dis. 2022 Jul 30;7(8):156. doi: 10.3390/tropicalmed7080156. PMID: 36006248; PMCID: PMC9414946. 2: Weawsiangsang S, Rattanachak N, Jongjitvimol T, Jaifoo T, Charoensit P, Viyoch J, Ross S, Ross GM, Baldock RA, Jongjitwimol J. Hydroquinine Inhibits the Growth of Multidrug-Resistant Pseudomonas aeruginosa via the Suppression of the Arginine Deiminase Pathway Genes. Int J Mol Sci. 2023 Sep 10;24(18):13914. doi: 10.3390/ijms241813914. PMID: 37762218; PMCID: PMC10530414. 3: Weawsiangsang S, Rattanachak N, Ross S, Ross GM, Baldock RA, Jongjitvimol T, Jongjitwimol J. Hydroquinine Enhances the Efficacy of Contact Lens Solutions for Inhibiting Pseudomonas aeruginosa Adhesion and Biofilm Formation. Antibiotics (Basel). 2024 Jan 5;13(1):56. doi: 10.3390/antibiotics13010056. PMID: 38247615; PMCID: PMC10812619. 4: van Kan HJ, Jansen PH, Tuinte C, Smits P, Verbeek AL. Hydroquinine pharmacokinetics after oral administration in adult patients with muscle cramps. Eur J Clin Pharmacol. 2000 Jun;56(3):263-7. doi: 10.1007/s002280000128. PMID: 10952483. 5: Rattanachak N, Weawsiangsang S, Daowtak K, Thongsri Y, Ross S, Ross G, Nilsri N, Baldock RA, Pongcharoen S, Jongjitvimol T, Jongjitwimol J. High-Throughput Transcriptomic Profiling Reveals the Inhibitory Effect of Hydroquinine on Virulence Factors in Pseudomonas aeruginosa. Antibiotics (Basel). 2022 Oct 19;11(10):1436. doi: 10.3390/antibiotics11101436. PMID: 36290094; PMCID: PMC9598861. 6: Liang W, Chen ZJ, Ran LH, Chen L. A Palladium-Catalyzed Borylation/Silica Gel Promoted Hydrolysis Sequence for the Synthesis of Hydroquinine-6'-Boric Acid and Its Applications. J Org Chem. 2023 Aug 4;88(15):11284-11298. doi: 10.1021/acs.joc.3c00774. Epub 2023 Jul 20. PMID: 37471456. 7: Jansen PH, Veenhuizen KC, Wesseling AI, de Boo T, Verbeek AL. Randomised controlled trial of hydroquinine in muscle cramps. Lancet. 1997 Feb 22;349(9051):528-32. doi: 10.1016/s0140-6736(97)80085-2. PMID: 9048790. 8: Jansen PH, Veenhuizen KC, Verbeek AL, Straatman H. Efficacy of hydroquinine in preventing frequent ordinary muscle cramp outlasts actual administration. J Neurol Sci. 1994 Apr;122(2):157-61. doi: 10.1016/0022-510x(94)90294-1. PMID: 8021700.