N-methylcytisine

Modify Date: 2024-01-01 18:14:13

N-methylcytisine structure	Common Name	N-methylcytisine
	CAS Number	486-86-2	Molecular Weight	204.27
	Density	1.2±0.1 g/cm3	Boiling Point	400.8±34.0 °C at 760 mmHg
	Molecular Formula	C₁₂H₁₆N₂O	Melting Point	137-139ºC
	MSDS	Chinese USA	Flash Point	191.9±18.0 °C
	Symbol	GHS07	Signal Word	Warning

Use of N-methylcytisine

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].

Name	N-Methylcytisine
Synonym	More Synonyms

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.

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

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

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

Formaldehyde

CAS#:50-00-0

Cytisine

CAS#:485-35-8

~99%

N-methylcytisine

CAS#:486-86-2

Literature: Frigerio, Fabio; Haseler, Claire A.; Gallagher, Timothy Synlett, 2010 , # 5 p. 729 - 730

Cytisine

CAS#:485-35-8

methyl iodide

CAS#:74-88-4

N-methylcytisine

CAS#:486-86-2

Literature: Tsypysheva; Koval'skaya; Makara; Lobov; Petrenko; Galkin; Sapozhnikova; Zarudii; Yunusov Chemistry of Natural Compounds, 2012 , vol. 48, # 4 p. 629 - 634 Khim. Prir. Soedin., 2012 , p. 565 - 570

Precursor 3
CAS#:50-00-0 Formaldehyde CAS#:485-35-8 Cytisine CAS#:74-88-4 methyl iodide
DownStream 0

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

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