LYCORINE

Base Information

• Chemical Name: LYCORINE
• CAS No.: 476-28-8
• Molecular Formula: C₁₆H₁₇NO₄
• Molecular Weight: 287.315
• European Community (EC) Number: 207-503-6
• NSC Number: 683873,401360
• UNII: I9Q105R5BU
• DSSTox Substance ID: DTXSID60197208
• Nikkaji Number: J5.973K
• Wikipedia: Lycorine
• Wikidata: Q420314
• Metabolomics Workbench ID: 53271
• ChEMBL ID: CHEMBL400092
• Mol file: 476-28-8.mol

Synonyms:Galanthan-1,2-diol,3,12-didehydro-9,10-[methylenebis(oxy)]-, (1a,2b)-; Galanthidine (7CI); Lycoran-1a,2b-diol, 3,3a-didehydro- (8CI); (-)-Lycorine;1H-[1,3]Dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol,2,4,5,7,12b,12c-hexahydro-, [1S-(1a,2b,12bb,12ca)]-; 3,3a-Didehydrolycoran-1a,2b-diol; 3,4-Didehydro-11,12-[methylenebis(oxy)]galanthan-1a,2b-diol; Amarylline; Lycorine; NSC 401360; NSC 683873;Narcissin; Narcissine

Chemical Property of LYCORINE

Chemical Property:

• Vapor Pressure: 6.37E-10mmHg at 25°C
• Melting Point: 253-255ºC (dec.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 477.4°Cat760mmHg
• PKA: 13.55±0.40(Predicted)
• Flash Point: 242.5°C
• PSA: 62.16000
• Density: 1.53g/cm³
• LogP: 0.68650
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 287.11575802
• Heavy Atom Count: 21
• Complexity: 481

Purity/Quality:

99% ^*data from raw suppliers

Lycorine >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

Useful:

• Canonical SMILES: C1CN2CC3=CC4=C(C=C3C5C2C1=CC(C5O)O)OCO4
• Isomeric SMILES: C1CN2CC3=CC4=C(C=C3[C@H]5[C@H]2C1=C[C@@H]([C@H]5O)O)OCO4
• Description: Lycoris radiate, a traditional Chinese medicine (TCM), is the bulb of the amaryllidaceous Lycoris radiata herb. It has been applied for clinical purposes for centuries. It is firstly recorded in Tujing Bencao and mainly used for the pyogenic infections. According to A Supplement to Compendium of Materia Medica, lycoris radiate may be used for treating acute throat trouble, phlegm node, baihuodan, and pulmonary abscess.There are about 20 Lycoris species in the world, which are widely distributed in China and Japan. Lycoris radiate is an amazing horticultural plant with a graceful shape and a bright color. In TCM, it is acrid in taste and neutral in nature, with functions of detoxication, easy expectoration, and diuresis and emesis promotion. According to the modern medicine, lycoris radiate is considered to be in favor of the central nervous system and cardiovascular system.The main active ingredients extracted from the lycoris herbs are about 40 alkaloids with various contents. Pharmacological tests indicate that galanthamine, lycorine, lycoramine, lycorenine, and crinine are the major effective medicinal ingredients. Lycorine may be used to treat amebic dysentery and against cancer. Moreover, galanthamine, dihydrogalanthamine, and lycoramine may be used to treat infantile paralysis and restore nerve functions and against traumatic paraplegia, etc. Lycoris radiate is famous because galanthamine has been approved by FDA as an anti-Alzheimer disease drug. Lycoris radiate is the only natural source for galanthamine with extremely low content (<0.02%).
• Physical properties: Appearance: colorless prismatic crystal. Solubility: insoluble in water; sparingly soluble in ethyl alcohol and diethyl ether. Melting point: 275–280?°C (decomposition). Specific optical rotation: right-handed optical rotation with a specific optical rotation of ?129° (98% ethyl alcohol).
• Uses: Lycorine is an analgesic, more so than aspirin, and a hypotensive, as are caranine and galanthine . The analgesic activity exhibited by the Amaryllidaceae alkaloids is attributed to their resemblance to the morphine and codeine skeletons. Lycorine also has antiarrhythmic action, and lycorine hydrochloride is a strong broncholytic. In fact, lycorine shows a relaxant effect on an isolated epinephrine-precontracted pulmonary artery and increases contractility and the rate of an isolated perfused heart. These effects are mediated by stimulation of b-adrenergic receptors.Lycorine also has a strong inhibitory effect on parasite (Encephalitozoon intestinalis) development and antifungal activity against Candida albicans. Additionally, lycorine has antifeedant, antimalarial, emetic, anti-inflammatory, antiplatelet , as well as antifertility activities. Galanthine, in turn, shows mild in vitro activity against Tripanosoma brucei rhodesiense and Plasmodium falciparum.
• Indications: Injection: 25?mg/ml, for resistance to amebic protozoa and treatment of intraintestinal/extraintestinal amebiasis. Subcutaneous injection: 25–50? mg/injection and 50?mg/day.
• Clinical Use: Dihydrolycorine, generated through the hydrogenation of lycorine, has been used clinically due to its better resistance against amebic dysentery and lower toxicity. The amine salt made of lycorine has an antitumor effect in animals.Lycorine exposure may cause skin irritation (red and swollen) and itching. Nosebleed may be induced in case of inhalation. In case of overdose, it may cause salivation, emesis, diarrhea, bradycardia, cold hands/feet, or even death due to respiratory center paralysis. The major studies of clinical application are focused on (1) antitumor effect, (2) effect on the central nervous system, (3) effect on the cardiovascular system, (4) anti-inflammatory effect, (5) effect on smooth muscle, and (6) emetic effect.

Technology Process of LYCORINE

There total 90 articles about LYCORINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.3%

(1S*,2R*,3R*)-3-phenylselanyldihydrolycorine (136612-59-4) → (±)-lycorine (476-28-8,6835-91-2,19312-40-4,66816-51-1)

Guidance literature:

With sodium periodate; In tetrahydrofuran; methanol; at 40 ℃; for 0.166667h;

DOI:10.1039/P19960000571

Reference yield: 48.4%

(1S,2S,3a1S,12bS)-2-chloro-2,3a1,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]-phenanthridin-1-yl acetate (69787-57-1) → (1aR,2a1S,11bS,11cS)-2a1,3,4,6,11b,11c-hexahydro-1aH-[1,3]dioxolo[4,5-j]oxireno[2,3-a]pyrrolo-[3,2,1-de]phenanthridine (15324-61-5) + 2-O-methyllycorine (6879-76-1) + lycorine (476-28-8,6835-91-2,19312-40-4,66816-51-1)

Guidance literature:

With potassium carbonate; In methanol; water; for 0.5h; Heating;

Reference yield:

(1S,2S,12bS,12cS)-1,2-diol-2,4,5,7,12b,12c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine hydrochloride (2188-68-3) → lycorine (476-28-8,6835-91-2,19312-40-4,66816-51-1)

Guidance literature:

With ammonium hydroxide; In water; at 20 ℃; for 16h;

DOI:10.1021/acs.orglett.8b02562

upstream raw materials:

(1S,2S,3a⁽¹⁾S,12bS)-7-oxo-2,3a⁽¹⁾,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrole[3,2,1-de]phenanthridine-1,2-diyl diacetate

(1S,2S,3a¹S,12bS)-2-chloro-2,3a¹,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]-phenanthridin-1-yl acetate

(1aR,2a¹S,11bS,11cS)-2a¹,3,4,6,11b,11c-hexahydro-1aH-[1,3]dioxolo[4,5-j]oxireno[2,3-a]pyrrolo-[3,2,1-de]phenanthridine

(1S,2S,12bS,12cS)-1-Ol-2-chloro-2,4,5,7,12b,12c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine

Downstream raw materials:

ungeremine

1-hydroxy-4,5-dihydro-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridinylium; chloride

ungeremine hydrochloride

7H-1,3-Dioxolo-4,5-j-pyrrolo-3,2,1-de-phenanthridine

Refernces

• 1、 Shin, Hyeong-Seob,Jung, Yong-Geun,Cho, Hyun-Kyu,Park, Yong-Gyu,Cho, Cheon-Gyu. "Total synthesis of (±)-Lycorine from the endo -cycloadduct of 3,5-dibromo-2-pyrone and (E)-β-borylstyrene". supporting information. p. 5718 - 5720. Retrieved 2015/02/19.
• 2、 Hoshino, Osamu,Ishizaki, Miyuki,Kamei, Keisuke,Taguchi, Minoru,Nagao, Takashi,et al.. "A New and Stereoselective Synthetic Route to an Amaryllidaceae Alkaloid, (+/-)-Lycorine". . p. 1365 - 1368. Retrieved 2007/10/02.