N-methylcytisine

Names

[ CAS No. ]:
486-86-2

[ Name ]:
N-methylcytisine

[Synonym ]:
N-methylcytisine
N－Methylcytisine
1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-
1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-, (1R)-
(1R)-11-Methyl-7,11-diazatricyclo[7.3.1.0]trideca-2,4-dien-6-one
11-Methyl-7,11-diazatricyclo[7.3.1.0]trideca-2,4-dien-6-one
1,2,3,4,5,6-Hexahydro-3-methyl-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
Caulophylline
3-methyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one
(1R)-3-methyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one

Biological Activity

[Description]:

N-Methylcytisine (Caulophylline), a tricyclic quinolizidine alkaloid, exerts hypoglycaemic, analgesic and anti-inflammatory activities. N-methylcytisine is a selective ligand of nicotinic receptors of acetylcholine in the central nervous system and has a high affinity (Kd = 50 nM) to nicotinic acetylcholine receptors (nAChR) from squid optical ganglia[1][2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Research Areas >> Inflammation/Immunology

[Target]

kd: 50 nM (nicotinic acetylcholine receptors)[2]

[References]

[1]. Jiao YF, et al. N-Methylcytisine Ameliorates Dextran-Sulfate-Sodium-Induced Colitis in Mice by Inhibiting the Inflammatory Response. Molecules. 2018 Feb 25;23(3). pii: E510.

[2]. Pliashkevich IuG, et al. [N-methylcytisine--a selective ligand of nicotinic receptors of acetylcholine in the CNS]. Biull Eksp Biol Med. 1987 Dec;104(12):690-2.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
400.8±34.0 °C at 760 mmHg

[ Melting Point ]:
137-139ºC

[ Molecular Formula ]:
C₁₂H₁₆N₂O

[ Molecular Weight ]:
204.27

[ Flash Point ]:
191.9±18.0 °C

[ Exact Mass ]:
204.126266

[ PSA ]:
25.24000

[ LogP ]:
0.46

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.616

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HA4400000

CHEMICAL NAME :: Cytisine, 12-methyl-

CAS REGISTRY NUMBER :: 486-86-2

BEILSTEIN REFERENCE NO. :: 0012448

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C12-H16-N2-O

MOLECULAR WEIGHT :: 204.30

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 511 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - muscle contraction or spasticity

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 :: 51 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - muscle contraction or spasticity

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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 22 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 79,334,1943

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 160 mg/kg

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

REFERENCE :: JOETD7 Journal of Ethnopharmacology. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1979- Volume(issue)/page/year: 7,24,1983

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
HA4400000

N-methylcytisine

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

Safety Information

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds