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

Description

Pyrrolizidine-7α-acetic acid methyl ester is a chemical compound predominantly found in plants from the Boraginaceae and Asteraceae families. It is recognized for its potential toxicity and hepatotoxicity, as it can be metabolized into harmful pyrrolic metabolites within the body. These metabolites are capable of inducing liver damage and have been associated with the development of liver tumors in animal studies.

Uses

Due to the toxic nature of pyrrolizidine-7α-acetic acid methyl ester, its uses are limited, and exposure should be avoided. However, it is important to be aware of its presence in certain plants and take necessary precautions when handling them to prevent any adverse health effects.

Upstream product

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

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.