526-64-7

Basic information

• Product Name: trachelanthamidine
• Synonyms: trachelanthamidine;(1R,7aS)-Hexahydro-1H-pyrrolizine-1-methanol;(1R,7aα)-1α-(Hydroxymethyl)hexahydro-1H-pyrrolizine;(1R-cis)-Hexahydro-1H-pyrrolizine-1-Methanol;2,3,5,6,7,7aα-Hexahydro-1H-pyrrolizine-1α-Methanol;TrachelanthaMidin;TracheoanthaMidine
• CAS NO: 526-64-7
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.21
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 526-64-7.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 201.6°Cat760mmHg
• Flash Point: 81.1°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0.0753mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: trachelanthamidine(CAS DataBase Reference)
• NIST Chemistry Reference: trachelanthamidine(526-64-7)
• EPA Substance Registry System: trachelanthamidine(526-64-7)

Safety Data

• Hazardous Substances Data: 526-64-7(Hazardous Substances Data)

Usage

Uses

Trachelanthamidine is a pyrrolizidine alkaloid as serotonin 5-HT4 receptor.

InChI:InChI=1/C8H15NO/c10-6-7-3-5-9-4-1-2-8(7)9/h7-8,10H,1-6H2/t7-,8-/m0/s1

Upstream product

• 119323-32-9 exo-(5S)-4-methoxycarbonyl-1-azabicyclo<3.3.0>octan-2-one 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 88790-37-8 (2S)-tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-2-carboxylate 
• 1528697-43-9 tert-butyl (1R,7S,αS)-7-[N-benzyl-N-(α-methylbenzyl)amino]cyclohept-3-ene-1-carboxylate 
• 1528697-72-4 (1R,7aS)-1-(tert-butoxycarbonyl)octahydropyrrolizin-4-ium acetate 
• 1528697-75-7 (1R,2S,5S,6S,αS)-2-[N-benzyl-N-(α-methylbenzyl)-amino]-5-hydroxy-7-oxabicyclo[4.2.1]nonan-8-one 
• 1528697-65-5 tert-butyl (1R,3R,4S,7S,αS)-3,4-dihydroxy-7-[N-benzyl-N-(α-methylbenzyl)amino]cycloheptane-1-carboxylate 
• 116836-78-3 (1R,8S)-1-iodomethyl-3-oxo-hexahydropyrrolizidine 
• 91240-39-0 3-oxo-hexahydro-pyrrolizine-1-carboxylic acid methyl ester 
• 63527-04-8 (1R,7aS)-Hexahydro-pyrrolizine-1-carboxylic acid ethyl ester 
• 111975-23-6 (S)-5-[(R)-3-Chloro-1-((S)-4-isopropyl-2-thioxo-thiazolidine-3-carbonyl)-propyl]-pyrrolidin-2-one 
• 147949-53-9 (1R,7aS)-Hexahydro-1-<(propanoyloxy)methyl>-3H-pyrrolizin-3-one 
• 103979-75-5 (1R,7aS)-hexahydro-3-oxo-3H-pyrrolizine-1-carbaldehyde 
• 903507-51-7 heliovicine 

Downstream Products

• 151898-33-8 SC 53606 
• 141196-99-8 4-amino-5-chloro-N-[(hexahydro-1H-pyrrolizin-1-yl)methyl]-2-methoxybenzamide 
• 879208-43-2 4-(acetylamino)-N-[(7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl]-5-chloro-2-methoxybenzamide 

Relevant articles and documents

Ipangulines and minalobines, chemotaxonomic markers of the infrageneric Ipomoea taxon subgenus Quamoclit, section Mina

A comprehensive GC-MS analysis of 8 Ipomoea species belonging to the subgenus Quamoclit, section Mina revealed that the members of this taxon form combinations of two necine bases with rare necic acids resulting in unique pyrrolizidine alkaloids. The occurrence and diversity of these metabolites show remarkable variations: Some species, especially Ipomoea hederifolia and Ipomoea lobata, are able to synthesize a large number of alkaloids whereas others, especially Ipomoea coccinea and Ipomoea quamoclit, are poor synthesizers with only a few compounds. However, these metabolites are apparently chemotaxonomic markers of this infrageneric taxon in general. They represent either esters of (-)-platynecine (altogether 48 ipangulines and 4 further esters including results of a previous study) or esters of (-)-trachelanthamidine, an additional novel structural type called minalobines (altogether 21 alkaloids). Both types are characterized by section-specific rare necic acids, e.g., ipangulinic/isoipangulinic acid, phenylacetic acid. The alkaloids of Ipomoea cholulensis, I. coccinea, I. hederifolia, Ipomoea neei, and Ipomoea quamoclit were mono and diesters of platynecine. Minalobines turned out to be metabolites of I. lobata (Cerv.) Thell. (syn.: Mina lobata Cerv.) lacking ipangulines. The major alkaloid of this species, minalobine R, has been isolated and identified as 9-O-(threo-2-hydroxy-2-methyl-3-phenylacetoxy-butyryl)-(-)-trachelanthamidine on the basis of spectral data. Apparently only two of the species included in this study, Ipomoea cristulata and Ipomoea sloteri, are able to synthesize both, ipangulines as well as minalobines. Minalobine O could be isolated as a major alkaloid of I. cristulata, its structure has been established as 9-O-(erythro-2-hydroxy-2-methyl-3-tigloyloxy-butyryl)-(-)-trachelanthamidine on the basis of spectral data.

Synthesis of (-)-trachelanthamidine using a single electron transfer reaction in 1,4-dimethylpiperazine

Synthesis of (-)-trachelanthamidine, one of the pyrrolizidine alkaloids, has been achieved by using a single electron transfer reaction of 2-(2-acetoxyethenyl)-N-(trichloroacetyl)pyrrolidine in boiling 1,4-dimethylpiperazine as the key step.

Asymmetric syntheses of (-)-isoretronecanol and (-)-trachelantamidine

Short and concise total asymmetric syntheses of (-)-isoretronecanol and (-)-trachelantamidine are reported. Oxidative cleavage of tert-butyl (S,S,S,Z)-7-[N-benzyl-N-(α-methylbenzyl)amino]cyclohept-3-ene-1- carboxylate, followed by hydrogenolysis promoted

Pyrrolizidine alkaloids from Liparis nervosa with inhibitory activities against LPS-induced NO production in RAW264.7 macrophages

Six pyrrolizidine alkaloids were isolated from the whole herb of Liparis nervosa together with two previously known ones. Their structures were elucidated by extensive spectroscopic analyses and chemical reactions. The cytotoxicity of the isolates was eva