78449-76-0

Basic information

• Product Name: pyrrolizidine-7α-acetic acid methyl ester
• Synonyms: pyrrolizidine-7α-acetic acid methyl ester;TETRAHYDRO-1H-PYRROLIZINE-7A(5H)-ACETIC ACID METHYL ESTER
• CAS NO: 78449-76-0
• Molecular Formula: C₁₀H₁₇NO₂
• Molecular Weight: 183.24748
• Mol File: 78449-76-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: pyrrolizidine-7α-acetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: pyrrolizidine-7α-acetic acid methyl ester(78449-76-0)
• EPA Substance Registry System: pyrrolizidine-7α-acetic acid methyl ester(78449-76-0)

Safety Data

• Hazardous Substances Data: 78449-76-0(Hazardous Substances Data)

Usage

General Description

Pyrrolizidine-7α-acetic acid methyl ester is a chemical compound that is primarily found in certain plants, such as those in the Boraginaceae and Asteraceae families. It is known for its potential toxic and hepatotoxic effects, as it can be metabolized in the body to form toxic pyrrolic metabolites. These metabolites can cause liver damage and have been linked to the development of liver tumors in animal studies. Due to its toxicity, exposure to pyrrolizidine-7α-acetic acid methyl ester should be avoided, and precautions should be taken when handling plants containing this compound.

Upstream product

• 67-56-1 methanol 
• 78449-75-9 (1-azabicyclo<3.3.0>octan-5-yl)acetonitrile 
• 40624-07-5 1,7-dichloro-4-heptanone 
• 20463-30-3 Δ¹⁽⁸⁾-dehydropyrrolizidine 
• 177719-25-4 1,7-Diiodoheptane-4-one 
• 6148-64-7 ethyl potassium malonate 
• 38330-80-2 monomethyl monopotassium malonate 
• 6739-80-6 γ-(N-2-pyrrolidinonyl)butyric acid 

Downstream Products

• 94794-30-6 7a-carboxymethylhexahydro-1H-pyrrolizine 
• 100445-98-5 (Tetrahydro-pyrrolizin-7a-yl)-acetyl chloride 

Relevant articles and documents

Facile entry to ethyl tetrahydro-1H-pyrrolizin-7a(5H)-ylacetate: A versatile pharmaceutical intermediate

An improved synthesis of ethyl tetrahydro-1H-pyrrolizin-7a(5H)-ylacetate is reported. This valuable pharmaceutical intermediate was easily obtained from 1,7-diiodo-4-heptanone in 46% yield, thus improving the procedure reported in the literature (23% yield) which starts from 1,7-dichloro-4-heptanone. Moreover, 1,7-diiodo-4-heptanone was obtained as an easily manageable solid, in this being preferable to its 1,7-dichloro isologue, which is a quite unstable oil. The former was synthesized in high overall yield (75%) starting from the commercially available diethyl 4-oxoheptanedioate, thus overtaking the well-known problems related to the use of γ-butyrolactone. The Japan Institute of Heterocyclic Chemistry.

Synthesis and muscarinic activity of a series of quinolines and naphthalenes with a 1-azabicyclo[3.3.0]octane moiety

In order to discover a medicine effective against Alzheimer's disease, we synthesized a series of quinoline derivatives having a characteristic 1- azabicyclo[3.3.0]octane amine ring, and performed pharmacological evaluation of them. Acetylcholine esterase inhibitory activities of these derivatives were unexpectedly weak. Tests for central nervous muscarinic cholinergic receptor binding affinity indicated that these compounds had higher affinities to muscarinic M1 receptors than to M2 receptors. A series of naphthalene derivatives substituted with the 1-azabicyclo[3.3.0]octane ring were also synthesized and muscarinic M1 and M2 receptor binding affinity determined. These compounds had much higher affinity for M1 receptors than the quinoline derivatives, and 1-[N-(1-azabicyclo[3.3.0]octan-5-yl)methyl-N- methylamino]-4-nitronaphthalene showed the highest affinity and selectivity. The ability of this compound to improve cognitive function was assessed using the passive avoidance test in scopolamine-induced mice.

A NEW ROUTE TO 8-SUBSTITUTED PYRRAZOLIZIDINES

A new route to 8-substituted pyrrazolizidines starting with Δ4(8)-dehydropyrrolizidinium perchlorate is described.