ChemicalBook > CAS DataBase List > narciclasine

narciclasine

Product Name: narciclasine
CAS No.: 29477-83-6
Chemical Name: narciclasine
Synonyms: rciclasin;NSC 266535;Narciclasin;BRN 1087400;Lycorcidinol;narciclasine;Lycoricidin-A;Narciclasine-RM;Narciclasine, 99.9%;Narciclasine, 10 mM in DMSO
CBNumber: CB41341322
Molecular Formula: C14H13NO7
Formula Weight: 307.26
MOL File: 29477-83-6.mol

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narciclasine Property

Melting point:: 250-252℃
Boiling point:: 447.77°C (rough estimate)
Density: 1.85±0.1 g/cm3 (20 ºC 760 Torr)
refractive index: 1.5300 (estimate)
storage temp.: Store at -20°C
solubility: DMSO: ≥10mg/mL
pka: 7.72±0.70(Predicted)
form: Solid
color: white to off-white
InChI: InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1
InChIKey: LZAZURSABQIKGB-AEKGRLRDSA-N
SMILES: C1=C2[C@@]([H])(NC(=O)C3C2=CC2OCOC=2C=3O)[C@H](O)[C@H](O)[C@H]1O

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Safety

Hazard Codes: Xn
Risk Statements: 46
Safety Statements: 36

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Danger
Hazard statements: H301Toxic if swalloed

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML2805
Product name: Narciclasine
Purity: ≥98% (HPLC)
Packaging: 1MG
Price: $147
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML2805
Product name: Narciclasine
Purity: ≥98% (HPLC)
Packaging: 5MG
Price: $599
Updated: 2025/07/31

Sigma-Aldrich

Product number: PHL82604
Product name: Narciclasine
Purity: phyproof? Reference Substance
Packaging: 10MG
Price: $1050
Updated: 2025/07/31

Cayman Chemical

Product number: 20361
Product name: Narciclasine
Purity: ≥98%
Packaging: 500μg
Price: $93
Updated: 2024/03/01

Cayman Chemical

Product number: 20361
Product name: Narciclasine
Purity: ≥98%
Packaging: 1mg
Price: $166
Updated: 2024/03/01

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narciclasine Chemical Properties,Usage,Production

Description

The bulbs of several Narcissus species contain this alkaloid which crystallizes in the form of pale yellow needles with a pronounced yellow-green fluorescence. It is best purified by recrystallization from either acetic acid or an aqueous mixture of methoxyethyl alcohol. It is dextrorotatory with [α]₅₈₉ + 145° or [Qh64 + 983° (c 1.5, EtOH). The ultraviolet spectrum in neutral solution (EtOH) has absorption maxima at 252, 302 and 329 mil, while that in alkaline solution (0.01 N/NaOH) has the maxima at 219, 249,310 and 355 mil. The O-methyl ether forms shiny needles which also exhibit a strong blue fluorescence. The tri_x0002_acetate has been prepared as an amorphous, non-crystallizable substance. With FeC13 the alkaloid gives a violet colour.

Description

Narciclasine is a plant growth inhibitor that can be isolated from Narcissus bulbs. At 1 μM, it has been shown to induce apoptosis-mediated cytotoxicity in human cancer cells in vitro but not in normal fibroblasts. Narciclasine has been shown to regulate the Rho/Rho kinase/LIM kinase/cofilin signaling pathway by increasing GTPase RhoA activity, as well as inducing actin stress fiber formation in a RhoA-dependent manner.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from narcissus.

Uses

Narciclasine is an antiproliferative and pro-apoptotic inducer.

Uses

Narciclasine is reasonably abundant in some Narcissus spp. and has served as a very useful intermediate for synthetic conversion into (+)-pancratistatin and to conduct a series of structure–activity relationship studies . Bicolorine, another member of the narciclasine series, is an unusual, completely aromatized quaternary alkaloid with an N-methyl group.

Definition

ChEBI: A natural product found in Narcissus pseudonarcissus.

target

Immunology & Inflammation related

storage

Store at -20°C

References

Ceriotti., Nature, 213,595 (1967)
Piozzi et al., Tetrahedron, 24, 1119 (1968)
Revised structure: Mondon, Krohn., Tetrahedron Lett., 2123 (1970)
Savona, Piozzi, Marino., Chern. Cornrnun., 1006 (1970)
Absolute configuration: Fuganti, Mazza.,J. Chern. Soc., Chern. Cornrnun., 239 (1972)
Crystal structure: Immirzi, Fuganti., J. Chern. Soc., Chern. Cornrnun., 240 (1972)
Stereochemistry: Mondon, Krohn., Tetrahedron Lett., 2085 (1972)

narciclasine Preparation Products And Raw materials

Raw materials

Preparation Products

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29477-83-6, narciclasineRelated Search:

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Narciclasin

Narciclasine, 99.9%

narciclasine

(13β)-1,19-Didehydro-2α,3β,4β,7-tetrahydroxy-11,12-dinor-5,19-secocrinan-6-one

(2S)-3,4,4aβ,5-Tetrahydro-2α,3β,4β,7-tetrahydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Lycorcidinol

(2S,3R,4S,4aR)-3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one

(2S-(2-alpha,3-beta,4-beta,4a-beta))-3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one

3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one

BRN 1087400

Lycoricidin-A

NSC 266535

rciclasin

[1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR)-

Rho-associated kinase,ROCK,inhibit,Inhibitor,ROK,Narciclasine,Rho-associated protein kinase,Rho-kinase

(2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Narciclasine-RM

Narciclasine, Rho/LIM kinase/cofilin signaling pathway activator

Narciclasine, 10 mM in DMSO

29477-83-6