486-86-2

Basic information

• Product Name: Caulophylline
• Synonyms: N-METHYLCYTISINE;(1r)-l;1,5-methano-8h-pyrido(1,2a)(1,5)diazocin-8-one,1,2,3,4,5,6-hexahydro-3-methy;1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-, (1R)-;1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-, (1R-cis)-;12-methyl-cytisin;12-Methylcytisine;Caulophyllin
• CAS NO: 486-86-2
• Molecular Formula: C₁₂H₁₆N₂O
• Molecular Weight: 204.27
• EINECS: 207-643-8
• Product Categories: Miscellaneous Reagents;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 486-86-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 137-139oC
• Boiling Point: 342.77°C (rough estimate)
• Flash Point: 191.9°C
• Appearance: /
• Density: 1.0565 (rough estimate)
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 9.61±0.20(Predicted)
• CAS DataBase Reference: Caulophylline(CAS DataBase Reference)
• NIST Chemistry Reference: Caulophylline(486-86-2)
• EPA Substance Registry System: Caulophylline(486-86-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: HA4400000
• Hazardous Substances Data: 486-86-2(Hazardous Substances Data)

Usage

Description

This 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.

Chemical Properties

Colourless Needles

Uses

N-Methylcytisine (cas# 486-86-2) is a compound useful in organic synthesis.

General Description

N-Methylcytisine is a nicotinic alkaloid found in Caulophyllum thalictroides, also known as blue cohosh.

Hazard

Extremely toxic; cardiotoxic; poisonous.

Biochem/physiol Actions

N-Methylcytisine is toxic and binds selectively to nicotinic acetylcholine receptors in the CNS.

References

Partheil., Arch. Pharm., 230,448 (1892) Power, Salway., J. Chem. Soc., 103, 194 (1913)

InChI:InChI=1/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

Upstream product

• 50-00-0 formaldehyd 
• 485-35-8 cytisine 
• 74-88-4 methyl iodide 

Downstream Products

• 1228275-14-6 11-methyl-8-(dimethylphenylsilyl)-7,11-diazatricyclo[7.3.1.0(2,7)]trideca-2,4-diene-6-one 
• 1401073-49-1 N-(12-methylcytisin-3-yl)-N-phenylurea 

Relevant articles and documents

Synthesis of Diels-Alder adducts of the quinolizidine alkaloids N-methylcytisine, (-)-leontidine, and (-)-thermopsine with N-phenylmaleimide

The Diels-Alder adducts of the quinolizidine alkaloids N-methylcytisine, (-)-leontidine, and (-)-thermopsine with N-phenylmaleimide have been synthesized. The structures and absolute configurations of the new asymmetric centers of the products were determ

The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside-Out” Approach

Bisquinolizidine alkaloids are characterized by a chiral bispidine core (3,7-diazabicyclo[3.3.1]nonane) to which combinations of an α,N-fused 2-pyridone, an endo- or exo-α,N-annulated piperidin(on)e, and an exo-allyl substituent are attached. We developed a modular “inside-out” approach that permits access to most members of this class. Its applicability was proven in the asymmetric synthesis of 21 natural bisquinolizidine alkaloids, among them more than ten first enantioselective total syntheses. Key steps are the first successful preparation of both enantiomers of C2-symmetric 2,6-dioxobispidine by desymmetrization of a 2,4,6,8-tetraoxo precursor, the construction of the α,N-fused 2-pyridone by using an enamine-bromoacrylic acid strategy, and the installation of endo- or, optionally, exo-annulated piperidin(on)es.

Synthesis and specific nootropic activity of (-)-cytisine derivatives with carbamide and thiocarbamide moieties in their structure

N-(methylcytisinyl)-N-substituted ureas, N-substituted cytisine-12- carbamides, and cytisine-12- thiocarbamide were prepared by reaction of (-)-cytisine with urea and thiourea and of (-)-cytisine and its 12-N-methyl-3-amino derivative with isocyanates. Their specific nootropic activity was studied in vivo. The therapeutic index was determined for the lead compound. Promising candidates for further pharmacological testing were found.