454-14-8

Basic information

• Product Name: Cuscohygrine
• Synonyms: 1,3-bis[(2s)-1-methylpyrrolidin-2-yl]propan-2-one;cuscohygrine;1,3-bis(1-methyl-2-pyrrolidinyl)acetone;1,3-BIS(1-METHYL-2-PYRROLIDINYL)PROPANONE;Cuskhygrine;Hellaradine;1,3-Bis[1-methylpyrrolidin-2-yl]propan-2-one;C06521
• CAS NO: 454-14-8
• Molecular Formula: C₁₃H₂₄N₂O
• Molecular Weight: 224.34246
• Product Categories: Heterocycles
• Mol File: 454-14-8.mol
• Article Data: 0

Chemical Properties

• Boiling Point: bp23 169-170°; bp14 152°; bp2 118-125°
• Flash Point: 118 °C
• Appearance: /
• Density: d420 0.9733
• Vapor Pressure: 0.000531mmHg at 25°C
• Refractive Index: nD20 1.4832
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Soluble), Ethyl Acetate, Methanol (Slightly)
• Stability: Solutions are unstable.
• CAS DataBase Reference: Cuscohygrine(CAS DataBase Reference)
• NIST Chemistry Reference: Cuscohygrine(454-14-8)
• EPA Substance Registry System: Cuscohygrine(454-14-8)

Safety Data

• Hazardous Substances Data: 454-14-8(Hazardous Substances Data)

Usage

Description

Cuscohygrine, also known as Datura alkaloid, is a primary alkaloid derived from medicinal plants such as Datura metel. It is characterized by its clear, colorless oil appearance and exhibits unique chemical properties that make it a promising candidate for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
Cuscohygrine is used as an active pharmaceutical ingredient for its medicinal properties. It is particularly effective in traditional medicine, where it has been used for centuries to treat various ailments due to its potent alkaloid content.
Used in Chemical Industry:
Cuscohygrine is used as a chemical intermediate for the synthesis of other compounds and pharmaceuticals. Its clear, colorless oil form makes it suitable for use in the chemical industry, where it can be further processed and utilized in the creation of various products.
Used in Research and Development:
Due to its unique chemical properties and potential applications, Cuscohygrine is also used in research and development for the discovery of new drugs and therapies. Its study can lead to a better understanding of its mechanisms of action and potential uses in modern medicine.

InChI:InChI=1/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3

Synthetic route

1-methyl-pyrrolidin-2-one (872-50-4) + acetonedicarboxylic acid (542-05-2) → cuscohygrine (454-14-8)

Conditions	Yield
With lithium aluminium tetrahydride anschliessende Decarboxylierung;

acetonedicarboxylic acid (542-05-2) + 4-methylamino-butyraldehyde (7729-27-3) → cuscohygrine (454-14-8)

Conditions	Yield
With aqueous solution of pH 7 Erhitzen des Reaktionsprodukts unter vermindertem Druck;

1,3-bis-(1-methyl-pyrrol-2-yl)-acetone (857419-87-5) → cuscohygrine (454-14-8)

Conditions	Yield
With palladium; acetic acid Hydrogenation;
With acetic acid; platinum Hydrogenation;

chromium(lll) acetate (1066-30-4) + dihydrocuscohygrine (80408-55-5, 80408-56-6) → cuscohygrine (454-14-8)

Conditions	Yield
isomer(ic) II;
isomer(ic) I;

1-methyl-pyrrolidin-2-one (872-50-4) + acetonedicarboxylic acid (542-05-2) + diethyl ether (60-29-7) + lithium alanate → cuscohygrine (454-14-8) + (+-)-hygrine

Conditions	Yield
in gepufferter wss. Loesung;

cuscohygrine (454-14-8) + methyl iodide (74-88-4) → 1,1,1',1'-tetramethyl-2,2'-(2-oxo-propanediyl)-bis-pyrrolidinium; diiodide (59884-19-4, 62209-22-7)

Conditions	Yield
With ethanol im Druckgefaess;

cuscohygrine (454-14-8) → (+/-)-hygrine (45771-52-6)

Conditions	Yield
With hydrogenchloride at 180℃;
With potassium hydroxide; diethyl ether laengeres Stehen;
With potassium hydroxide 8-stdg. Kochen;

cuscohygrine (454-14-8) → (1-methyl-pyrrolidin-2-yl)-acetic acid ethyl ester (5370-14-9)

Conditions	Yield
With nitrogen oxides; sodium ethanolate at 10 - 15℃;

cuscohygrine (454-14-8) → n-Undecane (1120-21-4) + 6-undecanol (23708-56-7)

Conditions	Yield
With ethanol; sodium erschoepfende Methylierung des Reaktionsgemisches und folgende Hydrierung mit Wasserstoff und kolloidalem Platin in 50 prozentiger Essigsaeure;

cuscohygrine (454-14-8) → 1,3-bis-(1-methyl-pyrrolidin-2-yl)-acetone-hydrazone

Conditions	Yield
With ethanol; hydrazine hydrate

cuscohygrine (454-14-8) → N-methylproline (68078-09-1)

Conditions	Yield
With chromium(III) oxide; sulfuric acid

cuscohygrine (454-14-8) → dihydrocuscohygrine (80408-55-5, 80408-56-6) + α-dihydrocuscohygrine

Conditions	Yield
With sodium amalgam; water isomer(ic) II;
With ethanol; sodium at 80℃; Trennung ueber das Pikrat; isomer(ic) II;

cuscohygrine (454-14-8) → dihydrocuscohygrine (80408-55-5, 80408-56-6) + β-dihydrocuscohygrine

Conditions	Yield
With sodium amalgam; water isomer(ic) I;
With ethanol; sodium at 80℃; Trennung von der β-Form ueber das Pikrat; isomer(ic) I;

cuscohygrine (454-14-8) → (1-methyl-pyrrolidin-2-yl)-acetone-hydrazone + cuscohygrine-hydrazone

Conditions	Yield
With ethanol; hydrazine hydrate

cuscohygrine (454-14-8) → (RS)-1-methylpyrrolidine-2-acetic acid (5626-43-7, 52484-80-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitrogen oxides; sodium ethylate / 10 - 15 °C 2: aq. barium hydroxide solution View Scheme

cuscohygrine (454-14-8) → 2-ethoxycarbonylmethyl-1,1-dimethyl-pyrrolidinium; iodide

Conditions	Yield
Multi-step reaction with 2 steps 1: nitrogen oxides; sodium ethylate / 10 - 15 °C 2: alcohol View Scheme

Upstream product

• 872-50-4 1-methyl-pyrrolidin-2-one 
• 542-05-2 acetonedicarboxylic acid 
• 60-29-7 diethyl ether 
• 1066-30-4 chromium(lll) acetate 
• 80408-55-5 dihydrocuscohygrine 
• 857419-87-5 1,3-bis-(1-methyl-pyrrol-2-yl)-acetone 
• 7729-27-3 4-methylamino-butyraldehyde 

Downstream Products

• 80408-55-5 dihydrocuscohygrine 
• 1120-21-4 n-Undecane 
• 23708-56-7 6-undecanol 
• 59884-19-4 Cuscohygrin-dimethoiodid