Cycleanine | CAS# 518-94-5 | bisbenzyl-bisisoquinoline alkaloid

MedKoo Cat#: 413403 | Name: Cycleanine

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Description:

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

Cycleanine is a bisbenzyl-bisisoquinoline alkaloid isolated from Chinese herb Stephania epigeae Lu; used for controlling blood pressure during anesthesia; isocycleanine is the R,S-isomer.

Chemical Structure

Cycleanine

CAS#518-94-5

Theoretical Analysis

MedKoo Cat#: 413403

Name: Cycleanine

CAS#: 518-94-5

Chemical Formula: C38H42N2O6

Exact Mass: 622.3043

Molecular Weight: 622.76

Elemental Analysis: C, 73.29; H, 6.80; N, 4.50; O, 15.41

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks
25mg	USD 1,150.00	2 Weeks

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Related CAS #

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Synonym

Cycleanine; O-Methylnorcycleanine; Dimethylisochondodendrine; (-)-Cycleanine

IUPAC/Chemical Name

(12aR,24aR)-2,3,12a,13,14,15,24,24a-octahydro-5,6,17,18-tetramethoxy-1,13-dimethyl-8,11:20,23-dietheno-1H,12H-[1,10]dioxacyclooctadecino[2,3,4-ij:11,12,13-i'j′]diisoquinoline

InChi Key

ANOXEUSGZWSCQL-LOYHVIPDSA-N

InChi Code

InChI=1S/C38H42N2O6/c1-39-17-15-25-21-31(41-3)35(43-5)37-33(25)29(39)19-23-7-11-28(12-8-23)46-38-34-26(22-32(42-4)36(38)44-6)16-18-40(2)30(34)20-24-9-13-27(45-37)14-10-24/h7-14,21-22,29-30H,15-20H2,1-6H3/t29-,30-/m1/s1

SMILES Code

CN1[C@@](CC2=CC=C3C=C2)([H])C4=C(CC1)C=C(OC)C(OC)=C4OC5=CC=C(C[C@](N(CC6)C)([H])C7=C6C=C(OC)C(OC)=C7O3)C=C5

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

>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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

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 622.76 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: Uche FI, McCullagh J, Claridge TWD, Richardson A, Li WW. Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells. Bioorg Med Chem Lett. 2018 May 15;28(9):1652-1656. doi: 10.1016/j.bmcl.2018.03.038. Epub 2018 Mar 16. PMID: 29588214. 2: Uche FI, Guo X, Okokon J, Ullah I, Horrocks P, Boateng J, Huang C, Li WW. In Vivo Efficacy and Metabolism of the Antimalarial Cycleanine and Improved In Vitro Antiplasmodial Activity of Semisynthetic Analogues. Antimicrob Agents Chemother. 2021 Jan 20;65(2):e01995-20. doi: 10.1128/AAC.01995-20. PMID: 33257443; PMCID: PMC7848973. 3: Uche FI, Drijfhout FP, McCullagh J, Richardson A, Li WW. Cytotoxicity Effects and Apoptosis Induction by Bisbenzylisoquinoline Alkaloids from Triclisia subcordata. Phytother Res. 2016 Sep;30(9):1533-9. doi: 10.1002/ptr.5660. Epub 2016 Jun 8. PMID: 27270992. 4: Satoh K, Nagai F, Ono M, Aoki N. Inhibition of Na(+),K(+)-ATPase by the extract of Stephania cephararantha HAYATA and bisbenzylisoquinoline alkaloid cycleanine, a major constituent. Biochem Pharmacol. 2003 Aug 1;66(3):379-85. doi: 10.1016/s0006-2952(03)00210-7. PMID: 12907236. 5: Martínez JA, Bello A, Rubio LL, Rodríguez C, Galán L, Caudales E, Alvarez JL. Calcium antagonist properties of the bisbenzylisoquinoline alkaloid cycleanine. Fundam Clin Pharmacol. 1998;12(2):182-7. doi: 10.1111/j.1472-8206.1998.tb00939.x. PMID: 9565772. 6: Bala M, Kumar S, Pratap K, Verma PK, Padwad Y, Singh B. Bioactive isoquinoline alkaloids from Cissampelos pareira †. Nat Prod Res. 2019 Mar;33(5):622-627. doi: 10.1080/14786419.2017.1402319. Epub 2017 Nov 10. PMID: 29126362. 7: Desgrouas C, Taudon N, Bun SS, Baghdikian B, Bory S, Parzy D, Ollivier E. Ethnobotany, phytochemistry and pharmacology of Stephania rotunda Lour. J Ethnopharmacol. 2014 Jul 3;154(3):537-63. doi: 10.1016/j.jep.2014.04.024. Epub 2014 Apr 25. PMID: 24768769. 8: Lohombo-Ekomba ML, Okusa PN, Penge O, Kabongo C, Choudhary MI, Kasende OE. Antibacterial, antifungal, antiplasmodial, and cytotoxic activities of Albertisia villosa. J Ethnopharmacol. 2004 Aug;93(2-3):331-5. doi: 10.1016/j.jep.2004.04.006. PMID: 15234773. 9: Otshudi AL, Apers S, Pieters L, Claeys M, Pannecouque C, De Clercq E, Van Zeebroeck A, Lauwers S, Frédérich M, Foriers A. Biologically active bisbenzylisoquinoline alkaloids from the root bark of Epinetrum villosum. J Ethnopharmacol. 2005 Oct 31;102(1):89-94. doi: 10.1016/j.jep.2005.05.021. PMID: 15996841. 10: Sun Z, Yang XY, Dai ZL, Jin GZ, Zhang ZD. [Hypotensive effect of dimethyl cycleanine bromide (author's transl)]. Zhongguo Yao Li Xue Bao. 1980 Sep;1(1):23-7. Chinese. PMID: 6175170.