MedKoo Cat#: 461427 | Name: Rotundine

Description:

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

Rotundine is an important traditional Chinese medicine agent contained in many kinds of sedative drugs.

Chemical Structure

Rotundine
Rotundine
CAS#6808-63-5

Theoretical Analysis

MedKoo Cat#: 461427

Name: Rotundine

CAS#: 6808-63-5

Chemical Formula: C19H21NO4

Exact Mass: 327.1471

Molecular Weight: 327.38

Elemental Analysis: C, 69.71; H, 6.47; N, 4.28; O, 19.55

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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Related CAS #
No Data
Synonym
Rotundine;
IUPAC/Chemical Name
(5S)-3,8-dimethoxy-13-methyl-5,6,11,12-tetrahydro-5,11-epiminodibenzo[a,e][8]annulene-2,9-diol
InChi Key
JLYWCHLTLCGOMW-LOACHALJSA-N
InChi Code
InChI=1S/C19H21NO4/c1-20-14-4-10-6-16(21)19(24-3)9-13(10)15(20)5-11-7-18(23-2)17(22)8-12(11)14/h6-9,14-15,21-22H,4-5H2,1-3H3/t14?,15-/m0/s1
SMILES Code
OC1=C(OC)C=C2C(CC3C4=CC(O)=C(OC)C=C4C[C@]2([H])N3C)=C1
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 327.38 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: Li JP, Zhou GM, Zhang LJ, Cheng HM, Qin HY. [IR and Raman spectra studies of Rotundine based on DFT]. Guang Pu Xue Yu Guang Pu Fen Xi. 2014 Nov;34(11):2989-93. Chinese. PubMed PMID: 25752044. 2: Li CZ, Lin QH, Zhuang XM, Xie JW, Li H. [In vitro O-demethylation of rotundine by recombinant human CYP isoenzymes]. Yao Xue Xue Bao. 2010 Mar;45(3):307-13. Chinese. PubMed PMID: 21351505. 3: Cui LL, Ma YS, Han HX. [Enhancing effect of volatile oils of rhizoma zingiberis, flos magnoliae and fructus litseae on permeation of rotundine in vitro]. Zhong Yao Cai. 2011 May;34(5):753-7. Chinese. PubMed PMID: 21954565. 4: KAWANISHI M, SUGASAWA S. ON THE STRUCTURE OF SO-CALLED ROTUNDINE. Chem Pharm Bull (Tokyo). 1965 Apr;13:522-4. PubMed PMID: 14294852. 5: Liu XJ, Xie SS, Zhang YX, Zhang JL, Zhang D, Wang YL, Ni D, Li D, Lu M, Ye QT. [Preparation of rotundine-chitosan gelled granules and their drug-release tests]. Yao Xue Xue Bao. 1991;26(10):782-7. Chinese. PubMed PMID: 1688072. 6: TRUTNEVA EA. [On the pharmacology of rotundine]. Farmakol Toksikol. 1961 May-Jun;24:279-84. Russian. PubMed PMID: 13778302. 7: Zhou M, Li X, Geng L, Qu C, Peng S. [Effect of rotundine on gastric acid and pepsin activity in rats]. Zhongguo Zhong Yao Za Zhi. 1998 May;23(5):301-3, inside back cover. Chinese. PubMed PMID: 11601318. 8: Zhao Y, Hellum BH, Liang A, Nilsen OG. Inhibitory Mechanisms of Human CYPs by Three Alkaloids Isolated from Traditional Chinese Herbs. Phytother Res. 2015 Jun;29(6):825-34. doi: 10.1002/ptr.5285. Epub 2015 Jan 30. PubMed PMID: 25640685. 9: Liu TT, Qu ZW, Qiu CY, Qiu F, Ren C, Gan X, Peng F, Hu WP. Inhibition of acid-sensing ion channels by levo-tetrahydropalmatine in rat dorsal root ganglion neurons. J Neurosci Res. 2015 Feb;93(2):333-9. doi: 10.1002/jnr.23484. Epub 2014 Nov 13. PubMed PMID: 25395088. 10: Zeng AY, Tu EY, Han ZY, Yang GT. [Effects of rotundine injection on nitric oxide synthase in tissues of different organs after ischemia/reperfusion of brain in rats]. Zhongguo Wei Zhong Bing Ji Jiu Yi Xue. 2007 Jun;19(6):361-4. Chinese. PubMed PMID: 17577446. 11: Zhou HH, Wu DL, Gao LY, Fang Y, Ge WH. L-Tetrahydropalmatine alleviates mechanical hyperalgesia in models of chronic inflammatory and neuropathic pain in mice. Neuroreport. 2016 May 4;27(7):476-80. doi: 10.1097/WNR.0000000000000560. PubMed PMID: 26981712. 12: Faison SL, Schindler CW, Goldberg SR, Wang JB. l-tetrahydropalmatine reduces nicotine self-administration and reinstatement in rats. BMC Pharmacol Toxicol. 2016 Nov 7;17(1):49. PubMed PMID: 27817750; PubMed Central PMCID: PMC5098281. 13: Li W, Zhao L, Le J, Zhang Y, Liu Y, Zhang G, Chai Y, Hong Z. Evaluation of Tetrahydropalmatine Enantiomers on the Activity of Five Cytochrome P450 Isozymes in Rats Using a Liquid Chromatography / Mass Spectrometric Method and a Cocktail Approach. Chirality. 2015 Aug;27(8):551-6. doi: 10.1002/chir.22469. Epub 2015 Jun 2. PubMed PMID: 26032585. 14: Wang JB, Mantsch JR. l-tetrahydropalamatine: a potential new medication for the treatment of cocaine addiction. Future Med Chem. 2012 Feb;4(2):177-86. doi: 10.4155/fmc.11.166. Review. PubMed PMID: 22300097; PubMed Central PMCID: PMC3878639. 15: Xiao W, Shen G, Zhuang X, Ran X, Zhu M, Li H. Characterization of human metabolism and disposition of levo-tetrahydropalmatine: Qualitative and quantitative determination of oxidative and conjugated metabolites. J Pharm Biomed Anal. 2016 Sep 5;128:371-381. doi: 10.1016/j.jpba.2016.06.015. Epub 2016 Jun 9. PubMed PMID: 27343900. 16: Li LP, Song FF, Weng YY, Yang X, Wang K, Lei HM, Ma J, Zhou H, Jiang HD. Role of OCT2 and MATE1 in renal disposition and toxicity of nitidine chloride. Br J Pharmacol. 2016 Aug;173(16):2543-54. doi: 10.1111/bph.13537. Epub 2016 Jul 9. PubMed PMID: 27324234; PubMed Central PMCID: PMC4959954. 17: Yu J, Che J, Liu L, Yang F, Zhu X, Cao B. Tetrahydropalmatine attenuates irradiation induced lung injuries in rats. Life Sci. 2016 May 15;153:74-81. doi: 10.1016/j.lfs.2016.03.056. Epub 2016 Apr 7. PubMed PMID: 27060221. 18: Zhao Y, Liang A, Zhang Y, Li C, Yi Y, Nilsen OG. Impact of Tetrahydropalmatine on the Pharmacokinetics of Probe Drugs for CYP1A2, 2D6 and 3A Isoenzymes in Beagle Dogs. Phytother Res. 2016 Jun;30(6):906-14. doi: 10.1002/ptr.5608. Epub 2016 Mar 17. Review. PubMed PMID: 26990021. 19: Sushchyk S, Xi ZX, Wang JB. Combination of Levo-Tetrahydropalmatine and Low Dose Naltrexone: A Promising Treatment for Prevention of Cocaine Relapse. J Pharmacol Exp Ther. 2016 May;357(2):248-57. doi: 10.1124/jpet.115.229542. Epub 2016 Feb 22. PubMed PMID: 26903543; PubMed Central PMCID: PMC4851325. 20: Gong X, Yue K, Ma B, Xing J, Gan Y, Wang D, Jin G, Li C. Levo-tetrahydropalmatine, a natural, mixed dopamine receptor antagonist, inhibits methamphetamine self-administration and methamphetamine-induced reinstatement. Pharmacol Biochem Behav. 2016 May;144:67-72. doi: 10.1016/j.pbb.2016.01.010. Epub 2016 Jan 21. PubMed PMID: 26806555.