616880-20-7

Basic information

• Product Name: Cyclohepta[b]pyran-5,8-imin-4(4aH)-one, 3-ethyl-5,6,7,8,9,9a-hexahydro-10-methyl-, (4aR,5R,8S,9aS)- (9CI)
• Synonyms: Cyclohepta[b]pyran-5,8-imin-4(4aH)-one, 3-ethyl-5,6,7,8,9,9a-hexahydro-10-methyl-, (4aR,5R,8S,9aS)- (9CI)
• CAS NO: 616880-20-7
• Molecular Formula: C13H19NO2
• Molecular Weight: 221.3
• Product Categories: ETHYL
• Mol File: 616880-20-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohepta[b]pyran-5,8-imin-4(4aH)-one, 3-ethyl-5,6,7,8,9,9a-hexahydro-10-methyl-, (4aR,5R,8S,9aS)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohepta[b]pyran-5,8-imin-4(4aH)-one, 3-ethyl-5,6,7,8,9,9a-hexahydro-10-methyl-, (4aR,5R,8S,9aS)- (9CI)(616880-20-7)
• EPA Substance Registry System: Cyclohepta[b]pyran-5,8-imin-4(4aH)-one, 3-ethyl-5,6,7,8,9,9a-hexahydro-10-methyl-, (4aR,5R,8S,9aS)- (9CI)(616880-20-7)

Safety Data

• Hazardous Substances Data: 616880-20-7(Hazardous Substances Data)

Upstream product

• 53-21-4 (-)-cocaine hydrochloride 
• 5796-31-6 ecgonine hydrochloride 
• 7143-09-1 methyl ecgonine 
• 616880-22-9 2-[(E)-tert-Butylimino-methyl]-1-((1R,3S,5S)-3-hydroxy-8-methyl-8-aza-bicyclo[3.2.1]oct-2-yl)-butan-1-one 

Relevant articles and documents

Synthesis and nicotinic binding studies on enantiopure pinnamine variants with an 8-azabicyclo[3.2.1]octane moiety

Bioisosteric replacement of the 9-azabicyclo[4.2.1]nonane pharmacophoric element of the novel alkaloidal marine toxine pinnamine (5) by the 8-azabicyclo[3.2.1]octane moiety resulted in conformationally restricted analogues 6a and 6c of (-)-ferruginine (4). Key step in the diastereoselective synthesis of these pyranotropanes was the condensation of enantiopure ecgonine methyl ester (9) from the "chiral pool" with the lithium anion of N-tert-butylbutyraldimin and subsequent cyclisation with TFA. The potential nAChR ligands were tested for their in vitro affinity for the (α4)2(β2)3 and the α7* nAChR subtypes. Despite obvious structural similarities with the potent alkaloids pinnamine (5) and (-)-ferruginine (4) the pyranotropanes 6a and 6c exhibited distinctly lower nAChR affinities.