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MedKoo Cat#: 112074 | Name: Scoulerine
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Description:

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

Scoulerine is a benzylisoquinoline alkaloid that selectively binds to the dopamine D1 and D2 receptors and inhibits proliferation in a panel of leukemia cell lines (IC50s = 2.7-6.5 µM).

Chemical Structure

Scoulerine
Scoulerine
CAS#6451-73-6

Theoretical Analysis

MedKoo Cat#: 112074

Name: Scoulerine

CAS#: 6451-73-6

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

Size Price Availability Quantity
1mg USD 300.00 2 Weeks
5mg USD 650.00 2 Weeks
10mg USD 1,000.00 2 Weeks
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Related CAS #
No Data
Synonym
Scoulerine; (–)-Scoulerine; l-Scoulerine; (S)-Scoulerine
IUPAC/Chemical Name
(S)-3,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,9-diol
InChi Key
KNWVMRVOBAFFMH-HNNXBMFYSA-N
InChi Code
InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
SMILES Code
OC1=C(C=C2CCN3CC4=C(C(OC)=CC=C4C[C@]3(C2=C1)[H])O)OC
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 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 J, Yan Z, Li H, Shi Q, Ahire V, Zhang S, Nimishetti N, Yang D, Allen TD, Zhang J. The Phytochemical Scoulerine Inhibits Aurora Kinase Activity to Induce Mitotic and Cytokinetic Defects. J Nat Prod. 2021 Aug 27;84(8):2312-2320. doi: 10.1021/acs.jnatprod.1c00429. Epub 2021 Aug 18. PMID: 34406008. 2: Tian J, Mo J, Xu L, Zhang R, Qiao Y, Liu B, Jiang L, Ma S, Shi G. Scoulerine promotes cell viability reduction and apoptosis by activating ROS-dependent endoplasmic reticulum stress in colorectal cancer cells. Chem Biol Interact. 2020 Aug 25;327:109184. doi: 10.1016/j.cbi.2020.109184. Epub 2020 Jun 24. PMID: 32590070. 3: Habartova K, Havelek R, Seifrtova M, Kralovec K, Cahlikova L, Chlebek J, Cermakova E, Mazankova N, Marikova J, Kunes J, Novakova L, Rezacova M. Scoulerine affects microtubule structure, inhibits proliferation, arrests cell cycle and thus culminates in the apoptotic death of cancer cells. Sci Rep. 2018 Mar 19;8(1):4829. doi: 10.1038/s41598-018-22862-0. PMID: 29555944; PMCID: PMC5859271. 4: Mi G, Gao Y, Yan H, Jin X, Ye E, Liu S, Gong Z, Yang H, Yang Z. l-Scoulerine attenuates behavioural changes induced by methamphetamine in zebrafish and mice. Behav Brain Res. 2016 Feb 1;298(Pt A):97-104. doi: 10.1016/j.bbr.2015.09.039. Epub 2015 Oct 1. PMID: 26433144. 5: Brochmann-Hanssen E, Nielsen B. The isolation of (minus)-scoulerine from opium. Tetrahedron Lett. 1966 May;20:2261-3. doi: 10.1016/s0040-4039(00)72411-7. PMID: 5923965. 6: Schrittwieser JH, Resch V, Wallner S, Lienhart WD, Sattler JH, Resch J, Macheroux P, Kroutil W. Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids. J Org Chem. 2011 Aug 19;76(16):6703-14. doi: 10.1021/jo201056f. Epub 2011 Jul 19. PMID: 21739961; PMCID: PMC3155283. 7: Wangchuk P, Sastraruji T, Taweechotipatr M, Keller PA, Pyne SG. Anti- inflammatory, Anti-bacterial and Anti-acetylcholinesterase Activities of two Isoquinoline Alkaloids-Scoulerine and Cheilanthifoline. Nat Prod Commun. 2016 Dec;11(12):1801-1804. PMID: 30508337. 8: Dubouzet JG, Morishige T, Fujii N, An CI, Fukusaki E, Ifuku K, Sato F. Transient RNA silencing of scoulerine 9-O-methyltransferase expression by double stranded RNA in Coptis japonica protoplasts. Biosci Biotechnol Biochem. 2005 Jan;69(1):63-70. doi: 10.1271/bbb.69.63. PMID: 15665469. 9: Muemmler S, Rueffer M, Nagakura N, Zenk MH. S-adenosyl-L-methionine: (S)-scoulerine 9-O-methyltransferase, a highly stereo- and regio-specific enzyme in tetrahydroprotoberberine biosynthesis. Plant Cell Rep. 1985 Feb;4(1):36-9. doi: 10.1007/BF00285501. PMID: 24253642. 10: Takeshita N, Fujiwara H, Mimura H, Fitchen JH, Yamada Y, Sato F. Molecular cloning and characterization of S-adenosyl-L- methionine:scoulerine-9-O-methyltransferase from cultured cells of Coptis japonica. Plant Cell Physiol. 1995 Jan;36(1):29-36. PMID: 7719631. 11: Rink E, Böhm H. Conversion of reticuline into scoulerine by a cell free preparation from Macleaya microcarpa cell suspension cultures. FEBS Lett. 1975 Jan 1;49(3):396-9. doi: 10.1016/0014-5793(75)80794-0. PMID: 234082.