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Lycorine

Lycorine structure

CAS No:
476-28-8
Formula:
C16H17NO4
Chemical Name:
Lycorine
Synonyms:
1H-[1,3]Dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol,2,4,5,7,12b,12c-hexahydro-,(1S,2S,12bS,12cS)-;Galanthidine;Lycoran-1α,2β-diol,3,3a-didehydro-;Galanthan-1,2-diol,3,12-didehydro-9,10-[methylenebis(oxy)]-,(1α,2β)-;(1S,2S,12bS,12cS)-2,4,5,7,12b,12c-Hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol;Amarylline;Lycorine;3,4-Didehydro-11,12-[methylenebis(oxy)]galanthan-1α,2β-diol;3,3a-Didehydrolycoran-1α,2β-diol;Narcissine;Narcissin;(-)-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-(1α,2β,12bβ,12cα)]-;NSC 401360;NSC 683873
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

Lycorine is a natural alkaloid extracted from the Amaryllidaceae plant family with antiviral, antimalarial and antiinflammation activities. Lycorine inhibits the growth and metastasis of hormone-refractory anti-prostate cancer (PCa) and induces cell apoptosis[1].

Lycorine is an indolizidine alkaloid that is 3,12-didehydrogalanthan substituted by hydroxy groups at positions and 2 and a methylenedioxy group across positions 9 and 10. Isolated from Crinum asiaticum, it has been shown to exhibit antimalarial activity. It has a role as a protein synthesis inhibitor, an antimalarial, a plant metabolite and an anticoronaviral agent. It derives from a hydride of a galanthan.

Lycorine Basic Attributes

Molecular Weight：

287.31

Exact Mass：

287.31

EC Number：

207-503-6

UNII：

I9Q105R5BU

NSC Number：

683873|401360

DSSTox ID：

DTXSID60197208

Characteristics

PSA：

62.2

XLogP3：

0.77

Appearance：

powder

Density：

1.5±0.1 g/cm3

Melting Point：

280 °C

Boiling Point：

477.4±45.0 °C at 760 mmHg

Flash Point：

242.5±28.7 °C

Refractive Index：

1.733

Storage Conditions：

2-8°C

Vapor Pressure：

6.37E-10mmHg at 25°C

Toxicity：

Oral-Mouse LD50: 10700 mg/kg; Subcutaneous-mouse LD50:145 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxide fumes

Specific rotation：

D16 -129° (c = 0.16 in 98% alc)

Safety Information

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

safety instructions：

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Precautionary statement(s)：

P264, P270, P301+P310, P321, P330, P405, P501

Hazard Statements：

H301

Toxicity

Toxicity class：

moderately toxic

Drug Information

MeSH Entry Terms：

2,4,5,7,12b,12c-hexahydro-1H-(1,3)dioxolo- (4,5-j)pyrrolo(3,2,1-de)phenanthridine-1,2-diol

Lycorine Use and Manufacturing

Methods of Manufacturing

This product is an isoquinoline alkaloid widely present in the Lycoris radiata plants, which can be extracted from the bulbs of Lycoris radiata.

Uses

Lycorycline has the effects of salivation, sub-heart and increasing tracheal secretion by oral administration or subcutaneous injection, so it has been used as an expectorant in some cases. Lycorisine has a significant effect of emetic. It is more potent than estrogen, but not as good as amorphine. Amaryllidine is hydrogenated to form dihydrolyricine, which has a strong anti-amebic dysentery effect and is less toxic, and is already available for clinical use. The lactam salt made from lycolide shows anti-tumor effect on animals. The traditional Chinese medicines Iron Arrow and Black Garlic have expectorant and leaf-reducing effects, and the reason is that they contain lycosine.

Computed Properties

Molecular Weight:287.31
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Exact Mass:287.11575802
Monoisotopic Mass:287.11575802
Topological Polar Surface Area:62.2
Heavy Atom Count:21
Complexity:481
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes