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MedKoo Cat#: 597041 | Name: Dicentrine, (-)-

Description:

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

Dicentrine, (-)- is an aporphinic alkaloid found in several plant species, mainly from Lauraceae family, which showed significant antinociceptive activity in an acute model of visceral pain in mice. It has also been shown to reduce spontaneous nociception and attenuating mechanical and cold hypersensitivity, probably via a TRPA1-dependent mechanism.

Chemical Structure

Dicentrine, (-)-
CAS#28832-07-7

Theoretical Analysis

MedKoo Cat#: 597041

Name: Dicentrine, (-)-

CAS#: 28832-07-7

Chemical Formula: C20H21NO4

Exact Mass: 339.1471

Molecular Weight: 339.39

Elemental Analysis: C, 70.78; H, 6.24; N, 4.13; O, 18.86

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Synonym
Dicentrine, (-)-; L-Dicentrine; NSC-251699; NSC 251699; NSC251699;
IUPAC/Chemical Name
(R)-10,11-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]benzo[g]quinoline
InChi Key
YJWBWQWUHVXPNC-CQSZACIVSA-N
InChi Code
InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m1/s1
SMILES Code
CN1CCC(C2=C3C4=CC(OC)=C(OC)C=C4C[C@@]12[H])=CC5=C3OCO5
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 339.39 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: Tiwari S, Awasthi M, Singh S, Pandey VP, Dwivedi UN. Modulation of interaction of mutant TP53 and wild type BRCA1 by alkaloids: a computational approach towards targeting protein-protein interaction as a futuristic therapeutic intervention strategy for breast cancer impediment. J Biomol Struct Dyn. 2017 Oct 23:1-12. doi: 10.1080/07391102.2017.1388286. [Epub ahead of print] PubMed PMID: 28978265. 2: Ma P, Li T, Ji F, Wang H, Pang J. Effect of GABA on blood pressure and blood dynamics of anesthetic rats. Int J Clin Exp Med. 2015 Aug 15;8(8):14296-302. eCollection 2015. PubMed PMID: 26550413; PubMed Central PMCID: PMC4613098. 3: Lin HF, Huang HL, Liao JF, Shen CC, Huang RL. Dicentrine Analogue-Induced G2/M Arrest and Apoptosis through Inhibition of Topoisomerase II Activity in Human Cancer Cells. Planta Med. 2015 Jul;81(10):830-7. doi: 10.1055/s-0035-1546128. Epub 2015 Jul 9. PubMed PMID: 26158522. 4: Dong JW, Cai L, Fang YS, Xiao H, Li ZJ, Ding ZT. Proaporphine and aporphine alkaloids with acetylcholinesterase inhibitory activity from Stephania epigaea. Fitoterapia. 2015 Jul;104:102-7. doi: 10.1016/j.fitote.2015.05.019. Epub 2015 May 29. PubMed PMID: 26028544. 5: Guterres Zda R, da Silva AF, Garcez WS, Garcez FR, Fernandes CA, Garcez FR. Mutagenicity and recombinagenicity of Ocotea acutifolia (Lauraceae) aporphinoid alkaloids. Mutat Res. 2013 Sep 18;757(1):91-6. doi: 10.1016/j.mrgentox.2013.07.004. Epub 2013 Jul 24. PubMed PMID: 23892138. 6: Montrucchio DP, Córdova MM, Santos AR. Plant derived aporphinic alkaloid S-(+)-dicentrine induces antinociceptive effect in both acute and chronic inflammatory pain models: evidence for a role of TRPA1 channels. PLoS One. 2013 Jul 4;8(7):e67730. doi: 10.1371/journal.pone.0067730. Print 2013. PubMed PMID: 23861794; PubMed Central PMCID: PMC3701576. 7: Kitisripanya T, Komaikul J, Tawinkan N, Atsawinkowit C, Putalun W. Dicentrine production in callus and cell suspension cultures of Stephania venosa. Nat Prod Commun. 2013 Apr;8(4):443-5. PubMed PMID: 23738448. 8: Montrucchio DP, Miguel OG, Zanin SM, da Silva GA, Cardozo AM, Santos AR. Antinociceptive effects of a chloroform extract and the alkaloid dicentrine isolated from fruits of Ocotea puberula. Planta Med. 2012 Sep;78(14):1543-8. Epub 2012 Jul 16. PubMed PMID: 22815198. 9: Rafamantanana MH, Debrus B, Raoelison GE, Rozet E, Lebrun P, Uverg-Ratsimamanga S, Hubert P, Quetin-Leclercq J. Application of design of experiments and design space methodology for the HPLC-UV separation optimization of aporphine alkaloids from leaves of Spirospermum penduliflorum Thouars. J Pharm Biomed Anal. 2012 Mar 25;62:23-32. doi: 10.1016/j.jpba.2011.12.028. Epub 2012 Jan 25. PubMed PMID: 22310553. 10: de Wet H, van Heerden FR, van Wyk BE. Alkaloidal variation in cissampelos capensis (Menispermaceae). Molecules. 2011 Apr 7;16(4):3001-9. doi: 10.3390/molecules16043001. PubMed PMID: 21475122. 11: Barinas JA, Suárez LE. Chemical constituents of Talauma arcabucoana (Magnoliaceae): their brine shrimp lethality and antimicrobial activity. Nat Prod Res. 2011 Sep;25(16):1497-504. doi: 10.1080/14786410903205146. Epub 2011 Jul 8. PubMed PMID: 21347974. 12: Lai YC, Kuo TF, Chen CK, Tsai HJ, Lee SS. Metabolism of dicentrine: identification of the phase I and phase II metabolites in miniature pig urine. Drug Metab Dispos. 2010 Oct;38(10):1714-22. doi: 10.1124/dmd.110.033795. Epub 2010 Jul 9. PubMed PMID: 20622045. 13: Konkimalla VB, Efferth T. Inhibition of epidermal growth factor receptor over-expressing cancer cells by the aphorphine-type isoquinoline alkaloid, dicentrine. Biochem Pharmacol. 2010 Apr 15;79(8):1092-9. doi: 10.1016/j.bcp.2009.11.025. Epub 2009 Dec 11. PubMed PMID: 20005213. 14: Putalun W, Yusakul G, Patanasethanont D. Dicentrine production from a hairy roots culture of Stephania suberosa. Z Naturforsch C. 2009 Sep-Oct;64(9-10):692-6. PubMed PMID: 19957438. 15: Liu Y, Deng A, Li X, Li Z, Zhang J, Du G, Qin H. [Exclusive control substance of radix Stephaniae tetrandrae]. Zhongguo Zhong Yao Za Zhi. 2009 Aug;34(15):1943-8. Chinese. PubMed PMID: 19894540. 16: Garcez WS, Garcez FR, da Silva LM, Hamerski L. Larvicidal activity against Aedes aegypti of some plants native to the West-Central region of Brazil. Bioresour Technol. 2009 Dec;100(24):6647-50. doi: 10.1016/j.biortech.2009.06.092. Epub 2009 Aug 6. PubMed PMID: 19664915. 17: Tsai TH, Wang GJ, Lin LC. Vasorelaxing alkaloids and flavonoids from Cassytha filiformis. J Nat Prod. 2008 Feb;71(2):289-91. doi: 10.1021/np070564h. Epub 2008 Jan 25. PubMed PMID: 18217715. 18: Konkimalla VB, Suhas VL, Chandra NR, Gebhart E, Efferth T. Diagnosis and therapy of oral squamous cell carcinoma. Expert Rev Anticancer Ther. 2007 Mar;7(3):317-29. Review. PubMed PMID: 17338652. 19: Ayers S, Zink DL, Mohn K, Powell JS, Brown CM, Murphy T, Brand R, Pretorius S, Stevenson D, Thompson D, Singh SB. Anthelmintic activity of aporphine alkaloids from Cissampelos capensis. Planta Med. 2007 Mar;73(3):296-7. Epub 2007 Feb 16. PubMed PMID: 17309014. 20: Asencio M, Hurtado-Guzmán C, López JJ, Cassels BK, Protais P, Chagraoui A. Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity. Bioorg Med Chem. 2005 Jun 1;13(11):3699-704. PubMed PMID: 15862999.