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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H16N2O
Molecular Weight 204.2682
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLCYTISINE

SMILES

CN1C[C@@H]2C[C@H](C1)C3=CC=CC(=O)N3C2

InChI

InChIKey=CULUKMPMGVXCEI-QVDQXJPCSA-N
InChI=1S/C12H16N2O/c1-13-6-9-5-10(8-13)11-3-2-4-12(15)14(11)7-9/h2-4,9-10H,5-8H2,1H3/t9?,10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C12H16N2O
Molecular Weight 204.2682
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/4387392 | https://www.ncbi.nlm.nih.gov/pubmed/17703777 | https://www.ncbi.nlm.nih.gov/pubmed/19137500 | https://www.ncbi.nlm.nih.gov/pubmed/10543898

Methylcytisine (Caulophylline) is a nicotinic alkaloid found in Caulophyllum thalictroides, also known as blue cohosh. Methylcytisine is a second potentially hazardous compound identified from blue cohosh. In cultured rat embryos, N-methylcytisine from blue cohosh caused major malformations. At a concentration of 20 ppm the effects included open anterior neural tube, poor or absent eye development, and twisted tail. Higher concentrations of Methylcytisine inhibited overall growth and morphogenesis, in addition to producing similar malformations. In a separate study, Methylcytisine was also found to stimulate the ganglion cells of the cardiac vagus in frogs, paralyze the ganglia of the cardiac vagus in dogs, and produce hyperglycemia in rabbits. Some of the actions of Methylcytisine are similar to nicotine. N-Methylcytisine in blue cohosh-containing dietary supplements has been measured at concentrations ranging from 5-850 ppm. No research has been conducted on the pharmacokinetics or pharmacodynamics of blue cohosh or its constituents; therefore, the clinical significance of the experiments discussed above remains unknown. However, women anticipating a pregnancy may want to avoid using blue cohosh-containing dietary supplements until the potential in vivo teratogenic effects of this botanical are understood.

Originator

Sources: Analyst (1911), 36, 270-1.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
The in vitro embryo culture system was used for activity evaluation. On gestation day 9.5, rat embryos were dissected from the dams at developmental stages 11a-11c, and cultured as previously described. The medium consisted of 2.0 mL rat serum and 0.5 mL Waymouth’s MB 752/1 medium containing penicillin-streptomycin (250 units and 250 mkg/mL). Methylcytisine was dissolved in a solution of EtOH-DMSO (1:1) and then added to the culture medium (10 mkL) at the beginning of culture. After 45 h in culture, embryonic development was assessed.
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:09:51 GMT 2023
Edited
by admin
on Fri Dec 15 20:09:51 GMT 2023
Record UNII
TT0MW69NCI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLCYTISINE
MI  
Common Name English
CYTISINE, 12-METHYL-
Common Name English
1,5-METHANO-8H-PYRIDO(1,2A)(1,5)DIAZOCIN-8-ONE, 1,2,3,4,5,6-HEXAHYDRO-3-METHYL-, (1R)-
Common Name English
CYTISINE, N-METHYL-
Common Name English
METHYLCYTISINE [MI]
Common Name English
CAULOPHYLLIN
Common Name English
CAULOPHYLLINE
Common Name English
N-METHYLCYTISINE
Common Name English
(1R)-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANO-8H-PYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE
Systematic Name English
12-METHYLCYTISINE
Common Name English
(-)-N-METHYLCYTISINE
Common Name English
1,5-METHANO-8H-PYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE, 1,2,3,4,5,6-HEXAHYDRO-3-METHYL-, (1R,5S)-
Systematic Name English
Code System Code Type Description
PUBCHEM
12302566
Created by admin on Fri Dec 15 20:09:51 GMT 2023 , Edited by admin on Fri Dec 15 20:09:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-643-8
Created by admin on Fri Dec 15 20:09:51 GMT 2023 , Edited by admin on Fri Dec 15 20:09:51 GMT 2023
PRIMARY
FDA UNII
TT0MW69NCI
Created by admin on Fri Dec 15 20:09:51 GMT 2023 , Edited by admin on Fri Dec 15 20:09:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID80876866
Created by admin on Fri Dec 15 20:09:51 GMT 2023 , Edited by admin on Fri Dec 15 20:09:51 GMT 2023
PRIMARY
CAS
486-86-2
Created by admin on Fri Dec 15 20:09:51 GMT 2023 , Edited by admin on Fri Dec 15 20:09:51 GMT 2023
PRIMARY
MERCK INDEX
m7391
Created by admin on Fri Dec 15 20:09:51 GMT 2023 , Edited by admin on Fri Dec 15 20:09:51 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT