495-19-2

Basic information

• Product Name: GUVACOLINE, HYDROBROMIDE
• Synonyms: GUVACINE METHYL ESTER, HYDROBROMIDE;GUVACOLINE, HYDROBROMIDE;NORARECOLINE;Norarecoline, Guvacine Methyl Ester, Hydrobromide,;1,2,5,6-Tetrahydro-3-pyridinecarboxylic acid methyl ester;1,2,3,6-tetrahydropyridine-5-carboxylic acid methyl ester;methyl 1,2,3,6-tetrahydropyridine-5-carboxylate;3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-, Methyl ester
• CAS NO: 495-19-2
• Molecular Formula: C₇H₁₁NO₂
• Molecular Weight: 222.08
• Product Categories: Nicotine Derivatives
• Mol File: 495-19-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 144°C
• Boiling Point: 209.1°Cat760mmHg
• Flash Point: 80.2°C
• Appearance: /
• Density: 1.074g/cm³
• Vapor Pressure: 0.207mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: GUVACOLINE, HYDROBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: GUVACOLINE, HYDROBROMIDE(495-19-2)
• EPA Substance Registry System: GUVACOLINE, HYDROBROMIDE(495-19-2)

Safety Data

• Hazardous Substances Data: 495-19-2(Hazardous Substances Data)

Usage

Chemical Properties

Guvacoline Hydrobromide is Crystalline Solid

Uses

3-Pyridinecarboxylic acid can be used as a useful tool in the identification of muscarinic receptors.

Definition

ChEBI: The methyl ester of guvacine.

InChI:InChI=1/C7H11NO2/c1-10-7(9)6-3-2-4-8-5-6/h3,8H,2,4-5H2,1H3

Upstream product

• 92600-27-6 1-(1-chloroethyl) 3-methyl 5,6-dihydropyridine-1,3(2H)-dicarboxylate 
• 851292-43-8 N-Fmoc-guvacine 
• 300-08-3 arecoline hydrobromide 
• 63-75-2 arecoline 
• 67-56-1 methanol 
• 121743-04-2 2-methoxycarbonylpenta-2,4-dienylamine 

Downstream Products

• 1234835-92-7 5-hydroxymethyl-1-p-toluenesulfonyl-1,2,3,6-tetrahydropyridine 
• 309748-80-9 (R)-tert-butyl 3-(phenylcarbamoyl)piperidine-1-carboxylate 
• 115103-54-3 tiagabine 

Relevant articles and documents

Synthesis of the ABC ring system of manzamine A.

A synthesis of the core ABC ring system of the manzamine alkaloids is described, starting from arecoline. The key steps involve a Claisen rearrangement to set up a 4-substituted-3-methylenepiperidine and a stereoselective azomethine ylide dipolar cycloaddition reaction. Condensation of the aldehyde 6 and sarcosine ethyl ester hydrochloride salt gives an intermediate azomethine ylide, which undergoes an intramolecular cycloaddition reaction to set up two new rings and three new chiral centers stereoselectively. The aldehyde 6 was not a suitable substrate for related azomethine ylide cycloaddition reactions with other amines. However, the related dimethyl acetal 26 could be condensed with a variety of amines to give the desired tricyclic products. The cycloaddition reaction with N-methyl or N-allyl glycine ethyl ester gave almost exclusively the exo adduct, whereas cycloaddition with glycine ethyl ester gave the endo adduct.

Collective total synthesis of tetracyclic diquinane lycopodium alkaloids (+)-paniculatine, (-)-magellanine, (+)-magellaninone and analogues thereof

The collective total synthesis of tetracyclic diquinane Lycopodium alkaloids, (+)-paniculatine, (-)-magellanine, (+)-magellaninone, and two analogues (-)-13-epi-paniculatine and (+)-3-hydroxyl-13-dehydro-paniculatine, has been accomplished. By logic-guide

Synthesis of 3-azabicyclo [4.1.0]heptane-1-carboxylic acid

A full study on the synthesis of 3-azabicyclo[4.1.0]heptane-1-carboxylic acid is described.Three different approaches were investigated in order to achieve an efficient synthesis of this unnatural aminoacid.The optimized synthetic route relies upon three key steps: (i) diazomalonate insertion on 4-phtalimido 1-butene, (ii) intramolecular cyclization and (iii) chemoselective reduction of the resulting lactam.Due to its bicyclic nature and conformational constraints, this aminoacid may be an useful building block in medicinal chemistry.