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485-35-8

485-35-8 structure
485-35-8 structure
  • Name: Cytisine
  • Chemical Name: cytisine
  • CAS Number: 485-35-8
  • Molecular Formula: C11H14N2O
  • Molecular Weight: 190.242
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-05-30 08:00:00
  • Modify Date: 2025-08-20 19:29:27
  • Cytisine is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus. Cytisine is a partial agonist of α4β2 nAChRs[1], and partial to full agonist at β4 containing receptors and α7 receptors[2]. has been used medically to help with smoking cessation[3].
Name cytisine
Synonyms CYTISINE
(1R,9S)-7,11-Diazatricyclo[7.3.1.0]trideca-2,4-dien-6-one
Cytitone
(1R)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido-[1,2-a][1,5]diazocin-8-one
1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
(1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one
MFCD00136048
Sophorin
Sophorin (VAN)
Ulexin
Cytisine (-)
Tabex
Tsitafat；Lupinidine
EINECS 207-616-0
Baptitoxin
(1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one
Tsitafat
(-)-Cytisine
Ulexine
Cytiton
Sophorine
Cytisin
Baptitoxine
Laburnin
Description Cytisine is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus. Cytisine is a partial agonist of α4β2 nAChRs[1], and partial to full agonist at β4 containing receptors and α7 receptors[2]. has been used medically to help with smoking cessation[3].
Related Catalog
Target

α4β2 nAChRs[1].

In Vitro Cytisine (2.5, 5 and 10 mM) is capable of inducing apoptosis in HepG2 cells[4]. Treatment with Cytisine increases the percentage of cells in the sub-G1 phase (P<0.01). The preincubation of HepG2 cells with Cytisine (2.5, 5 and 10 mM) significantly increases the sub-G1 cell population[4].
In Vivo Cytisine (5 mg/kg, i.p.) eat less and gain less weight than those that receive the vehicle[2]. Total pellet intake increases during Cytisine substitution relative to nicotine and animals self-administered Cytisine significantly less than nicotine[2].
References

[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.
Density 1.2±0.1 g/cm3
Boiling Point 413.0±34.0 °C at 760 mmHg
Melting Point 154-156ºC
Molecular Formula C11H14N2O
Molecular Weight 190.242
Flash Point 203.6±25.7 °C
Exact Mass 190.110611
PSA 34.03000
LogP 0.07
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.623

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
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H315-H319-H335
Precautionary Statements P305 + P351 + P338
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic
Risk Phrases R25;R36/37/38
Safety Phrases S26-S28-S36/37-S45
RIDADR UN 2811
WGK Germany 3
RTECS HA4025000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2933990090
HS Code 2933990090
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%
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