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MedKoo Cat#: 413686 | Name: Dicentrine HCl

Description:

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

Dicentrine HCl is the salt form of Dicentrine, an alpha 1-adrenoceptor antagonist effective against human hyperplastic prostates.

Chemical Structure

Dicentrine HCl
CAS#5742-03-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 413686

Name: Dicentrine HCl

CAS#: 5742-03-0 (HCl)

Chemical Formula: C20H22ClNO4

Exact Mass: 375.1237

Molecular Weight: 375.85

Elemental Analysis: C, 63.91; H, 5.90; Cl, 9.43; N, 3.73; O, 17.03

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
Dicentrine HCl; Dicentrine hydrochloride
IUPAC/Chemical Name
5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, hydrochloride (S)
InChi Key
KEPNLLUUOISJKZ-UQKRIMTDSA-N
InChi Code
InChI=1S/C20H21NO4.ClH/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;1H/t14-;/m0./s1
SMILES Code
CN1CCC(C2=C3C4=CC(OC)=C(OC)C=C4C[C@]12[H])=CC5=C3OCO5.[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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 375.85 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
1: 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. 2: 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. 3: Yu SM, Ko FN, Chueh SC, Chen J, Chen SC, Chen CC, Teng CM. Effects of dicentrine, a novel alpha 1-adrenoceptor antagonist, on human hyperplastic prostates. Eur J Pharmacol. 1994 Jan 24;252(1):29-34. PubMed PMID: 7512043. 4: 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. 5: Teng CM, Yu SM, Ko FN, Chen CC, Huang YL, Huang TF. Dicentrine, a natural vascular alpha 1-adrenoceptor antagonist, isolated from Lindera megaphylla. Br J Pharmacol. 1991 Nov;104(3):651-6. PubMed PMID: 1686739; PubMed Central PMCID: PMC1908254. 6: Mustafa MR, Achike FI. Dicentrine is preferentially antagonistic to rat aortic than splenic alpha 1-adrenoceptor stimulation. Acta Pharmacol Sin. 2000 Dec;21(12):1165-8. PubMed PMID: 11603294. 7: Yu SM, Hsu SY, Ko FN, Chen CC, Huang YL, Huang TF, Teng CM. Haemodynamic effects of dicentrine, a novel alpha 1-adrenoceptor antagonist: comparison with prazosin in spontaneously hypertensive and normotensive Wistar-Kyoto rats. Br J Pharmacol. 1992 Aug;106(4):797-801. PubMed PMID: 1356567; PubMed Central PMCID: PMC1907686. 8: Young ML, Su MJ, Wu MH, Chen CC. The electrophysiological effects of dicentrine on the conduction system of rabbit heart. Br J Pharmacol. 1994 Sep;113(1):69-76. PubMed PMID: 7812635; PubMed Central PMCID: PMC1510066. 9: Li HL, Zhang RP, Ye HT, Wang H. [Effect of L-dicentrine on contraction of rat stomach muscle strips]. Zhongguo Zhong Yao Za Zhi. 2000 Jul;25(7):426-8. Chinese. PubMed PMID: 12515226. 10: 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. 11: Huang RL, Chen CC, Huang YL, Ou JC, Hu CP, Chen CF, Chang C. Anti-tumor effects of d-dicentrine from the root of Lindera megaphylla. Planta Med. 1998 Apr;64(3):212-5. PubMed PMID: 9581516. 12: Su MJ, Nieh YC, Huang HW, Chen CC. Dicentrine, an alpha-adrenoceptor antagonist with sodium and potassium channel blocking activities. Naunyn Schmiedebergs Arch Pharmacol. 1994 Jan;349(1):42-9. PubMed PMID: 7908125. 13: Yu SM, Kang YF, Chen CC, Teng CM. Effects of dicentrine on haemodynamic, plasma lipid, lipoprotein level and vascular reactivity in hyperlipidaemic rats. Br J Pharmacol. 1993 Apr;108(4):1055-61. PubMed PMID: 8485617; PubMed Central PMCID: PMC1908156. 14: Yu SM, Chen CC, Ko FN, Huang YL, Huang TF, Teng CM. Dicentrine, a novel antiplatelet agent inhibiting thromboxane formation and increasing the cyclic AMP level of rabbit platelets. Biochem Pharmacol. 1992 Jan 22;43(2):323-9. PubMed PMID: 1310852. 15: 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. 16: Dong JW, Li XJ, Cai L, Shi JY, Li YF, Yang C, Li ZJ. Simultaneous determination of alkaloids dicentrine and sinomenine in Stephania epigeae by (1)H NMR spectroscopy. J Pharm Biomed Anal. 2018 Oct 25;160:330-335. doi: 10.1016/j.jpba.2018.08.007. Epub 2018 Aug 6. PubMed PMID: 30114611. 17: Chang KC, Lo HM, Lin FY, Tseng YZ, Ko FN, Teng CM. Effects of dicentrine on the mechanical properties of systemic arterial trees in dogs. J Cardiovasc Pharmacol. 1995 Jul;26(1):169-76. PubMed PMID: 7564359. 18: Heng HL, Chee CF, Thy CK, Tee JT, Chin SP, Herr DR, Buckle MJC, Paterson IC, Doughty SW, Abd Rahman N, Chung LY. In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5-HT(2) and α(1) receptors. Chem Biol Drug Des. 2019 Feb;93(2):132-138. doi: 10.1111/cbdd.13390. Epub 2018 Oct 3. PubMed PMID: 30216681. 19: Yodkeeree S, Ooppachai C, Pompimon W, Limtrakul Dejkriengkraikul P. O-Methylbulbocapnine and Dicentrine Suppress LPS-Induced Inflammatory Response by Blocking NF-κB and AP-1 Activation through Inhibiting MAPKs and Akt Signaling in RAW264.7 Macrophages. Biol Pharm Bull. 2018;41(8):1219-1227. doi: 10.1248/bpb.b18-00037. PubMed PMID: 30068871. 20: 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.