金雀花碱

金雀花碱用途

Cytisine 是一种生物碱,可在 Laburnum 和 Cytisus 等中提取得到。 Cytisine 是 α4β2 烟碱乙酰胆碱能受体 (α4β2 nAChRs) 的部分激动剂[1],也是包含 β4 受体和 α7 受体的偏完全性激动剂[2]。医学上已被用于帮助戒烟[3]。

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金雀花碱名称

[ CAS 号 ]:
485-35-8

[ 中文名 ]:
金雀花碱

[ 英文名 ]:
Cytisine

[中文别名 ]:

[英文别名 ]:

CYTISINE
Cytitone
MFCD00136048
Sophorin
Sophorin (VAN)
Ulexin
Cytisine (-)
Tabex
Tsitafat；Lupinidine
EINECS 207-616-0

金雀花碱生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 跨膜转运 >> 胆碱受体

信号通路 >> 神经信号通路 >> 胆碱受体

研究领域 >> 代谢疾病

[ 靶点 ]

α4β2 nAChRs[1].

[体外研究]

Cytisine(2.5,5和10 mM)能够诱导HepG2细胞凋亡[4]。用Cytisine治疗增加了亚G1期细胞的百分比(P <0.01)。用Cytisine(2.5,5和10 mM)预孵育HepG2细胞可显着增加亚G1细胞群[4]。

[体内研究]

Cytisine(5 mg/kg,ip)吃得少,体重也比接受载体的人少[2]。 Cytisine替代期间相对于尼古丁的总颗粒摄入量增加,并且自我施用Cytisine的动物显着少于尼古丁[2]。

[参考文献]

[1]. Pabreza LA, et al. [3H]cytisine binding to nicotinic cholinergic receptors in brain. Mol Pharmacol. 1991 Jan;39(1):9-12.

[2]. Grebenstein PE, et al. The effects of noncontingent and self-administered cytisine on body weight and meal patterns in male Sprague-Dawley rats. Pharmacol Biochem Behav. 2013 Sep;110:192-200.

[3]. Walker N, et al. Cytisine versus nicotine for smoking cessation. N Engl J Med. 2014 Dec 18;371(25):2353-62.

[4]. Yu L, et al. Cytisine induces endoplasmic reticulum stress caused by calcium overload in HepG2 cells. Oncol Rep. 2018 Mar;39(3):1475-1484.

[相关活性小分子]

金雀花碱物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
413.0±34.0 °C at 760 mmHg

[ 熔点 ]:
154-156ºC

[ 分子式 ]:
C₁₁H₁₄N₂O

[ 分子量 ]:
190.242

[ 闪点 ]:
203.6±25.7 °C

[ 精确质量 ]:
190.110611

[ PSA ]:
34.03000

[ LogP ]:
0.07

[ 外观性状 ]:
灰白色至黄褐色的结晶固体

[ 蒸汽压 ]:
0.0±1.0 mmHg at 25°C

[ 折射率 ]:
1.623

[ 储存条件 ]:
室温

[ 水溶解性 ]:
水溶性：可溶；可溶于：乙醇,甲醇；微溶：苯,丙酮

金雀花碱MSDS

金雀花碱毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HA4025000

CHEMICAL NAME :: Cytisine

CAS REGISTRY NUMBER :: 485-35-8

BEILSTEIN REFERENCE NO. :: 0083882

LAST UPDATED :: 199709

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C11-H14-N2-O

MOLECULAR WEIGHT :: 190.27

WISWESSER LINE NOTATION :: T C666 A GVN LM&TTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 8750 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 4(1),34,1941

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 101 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - rigidity (including catalepsy)

REFERENCE :: BJPCBM British Journal of Pharmacology. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.34- 1968- Volume(issue)/page/year: 35,161,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8550 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 18,214,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 11764 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 4(1),34,1941

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1730 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - rigidity (including catalepsy)

REFERENCE :: BJPCBM British Journal of Pharmacology. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.34- 1968- Volume(issue)/page/year: 35,161,1969

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 16 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85IXA4 "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948 Volume(issue)/page/year: -,589,1948

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity

REFERENCE :: ITOBAO Izvestiya Akademii Nauk Tadzhikskoi SSR, Otdelenie Biologicheskikh Nauk. Proceedings of the Academy of Sciences of the Tadzhik SSR, Department of Biological Sciences. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) No.1- 1962- Volume(issue)/page/year: (2),104,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 4(1),34,1941

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85IXA4 "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948 Volume(issue)/page/year: -,589,1948 *** REVIEWS *** TOXICOLOGY REVIEW CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 12,1,1978 TOXICOLOGY REVIEW PISDDJ Pacific Information Service on Street Drugs. (J.K. Brown, School of Pharmacy, Univ. of the Pacific, Stockton, CA 95211) V.1- 1972(?)- Volume(issue)/page/year: 5(3-6),-,1977

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金雀花碱安全信息

[ 符号 ]:

GHS06

[ 信号词 ]:
Danger

[ 危害声明 ]:
H301-H315-H319-H335

[ 警示性声明 ]:
P305 + P351 + P338

[ 个人防护装备 ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
T:Toxic

[ 风险声明 (欧洲) ]:
R25;R36/37/38

[ 安全声明 (欧洲) ]:
S26-S28-S36/37-S45

[ 危险品运输编码 ]:
UN 2811

[ WGK德国 ]:
3

[ RTECS号 ]:
HA4025000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1(b)

[ 海关编码 ]:
2933990090

金雀花碱合成路线

金雀花碱上下游产品

金雀花碱上游产品

金雀花碱下游产品

金雀花碱海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

金雀花碱文献

Differential expression of the beta4 neuronal nicotinic receptor subunit affects tolerance development and nicotinic binding sites following chronic nicotine treatment.

Pharmacol. Biochem. Behav. 130 , 1-8, (2015)

The role of neuronal nicotinic acetylcholine receptors (nAChR) containing the β4 subunit in tolerance development and nicotinic binding site levels following chronic nicotine treatment was investigate...

Pharmacokinetics of cytisine, an α4 β2 nicotinic receptor partial agonist, in healthy smokers following a single dose.

Drug Test. Anal. , doi:10.1002/dta.1707, (2014)

Cytisine, an α4 β2 nicotinic receptor partial agonist, is a plant alkaloid that is commercially extracted for use as a smoking cessation medication. Despite its long history of use, there is very litt...

Synthesis and pharmacological evaluation of novel 9- and 10-substituted cytisine derivatives. Nicotinic ligands of enhanced subtype selectivity.

J. Med. Chem. 49 , 2673-2676, (2006)

We report the synthesis and pharmacological properties of several cytisine derivatives. Among them, two 10-substituted derivatives showed much higher selectivities for the alpha4beta2 nAChR subtype in...

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