N-Methylcytisine
Basic information
- CAS
486-86-2- Standard SMILES
CN1C[C@@H]2C[C@H](C1)c1cccc(=O)n1C2- InChIKey
CULUKMPMGVXCEI-VHSXEESVSA-N- Molecular formula
- C12H16N2O
- Average molar mass
- 204.27 g/mol
- Monoisotopic mass
- 204.12626314
Overview
N-methylcytisine has been reported in Euchresta horsfieldii, Ormosia emarginata, and other organisms with data available.
Names & identifiers
- Preferred name
- N-Methylcytisine
- IUPAC
- (1R,9S)-11-methyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
- English name
- Caulophylline
- Molecular formula
- C12H16N2O
- Molecular weight
- 204.27
Names & synonyms
N-MethylcytisineN-methyl-cytisine(1R,9S)-11-methyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-, (1R)-(1R,9S)-11-methyl-7,11-diazatricyclo(7.3.1.02,7)trideca-2,4-dien-6-oneRefChem:390983486-86-2Caulophyllin12-Methylcytisine(-)-N-methylcytisine3-MethylcytisineCYTISINE, 12-METHYL-
Show more names
Methylcytisine(1r)-lCaulophylline12-methyl-cytisinN-Methylcytisine-RM
N pound-MethylcytisineMFCD00211091N-Methylcytisine (Standard)CHEMBL10850455-24-02-00538 (Beilstein Handbook Reference)(1R,5S)-3-Methyl-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one(1R,5S)-3-methyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one1,5-Methano-8H-pyrido(1,2a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-, (1R)-
Database identifiers
- CAS
486-86-2、63699-79-6- PubChem CID
- 670971
- DTXSID
DTXSID80876866- ChEMBL
CHEMBL1085045- UNII
- TT0MW69NCI
- Nikkaji
- J9.380G
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 23.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 359
Physicochemical properties
- Melting point
- 137 · 137-139oC
- alpha
- 30 D · 30D -224° (c = 1.05 in water)
- Boiling point
- 342.77 °C · 342.77°C (rough estimate)
- Density
- 1.0565 · 1.0565 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- -20 °C · -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- form
- powder
- pka
- 9.61 · 9.61±0.20(Predicted)
- color
- White to Off-White
- InChI
- 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+/m0/s1
- InChIKey
- CULUKMPMGVXCEI-VHSXEESVSA-N
- SMILES
- N12C(=O)C=CC=C1[C@]1([H])C[C@]([H])(C2)CN(C)C1
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 MW69NCI · TT0MW69NCI
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- HA4400000
- Toxicity
- LD50 in mice (mg/kg): 21 i.v.; 51 i.p. (Barlow, McLeod)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
- Precautionary statements
- P261-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312
Chemistry & industry
Applications
DescriptionThis base was first prepared synthetically by Partheil and subsequently discovered in the roots of Caulophyllurn thalictroides L. It is widespread among the Papilionaceae, being found in Baptisia australis, Genista tinctoria, Sophora microphylla, S. tetraptera, Thermopsis lanceolata and T. rhombifolia (Watt.) Richards. It is laevorotatory with [α]20D - 221 ° (H20) and furnishes the following crystalline salts and derivatives: hydrochloride, m.p. 2S0-SoC (dec.); hydriodide, m.p. 246-7°C (dec.); perchlorate, m.p. 2S4°C (dec.); aurichloride, m.p. 206°C (dec.); picrate, m.p. 230°C; picrolonate, m.p. 224-SoC (dec.) and the methiodide which occurs in two modifications, m.p. 248°C and 267-276°C.
UsesN-Methylcytisine (cas# 486-86-2) is a compound useful in organic synthesis.
General DescriptionN-Methylcytisine is a nicotinic alkaloid found in Caulophyllum thalictroides, also known as blue cohosh.
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