Hypotensive and Ganglion blocking action of methyl substituted 3-amino-norcamphanes

Pedersen, J. G. A.; Fakstorp, Jørgen; Rønnov-Jessen, Vagn

doi:10.1007/bf02159100

Cited by 13 publications

(5 citation statements)

References 3 publications

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“…in this test. The greater potency of amine, as compared with quaternary, ganglion-blocking compounds in this test has been described for pempidine by Corne and Edge (1958), and Stone, Meckelnburg, and Torchiana (1958) R0nnov-Jessen (1958) have reported that a compound with this planar P A N H P A N H P A N H P A N IH P A N 2.5 170.5 182.5…”

Section: Four Structural Isomers Of Mecamylaminesupporting

confidence: 57%

“…None of these results was thought worth following up. A compound with an identical planar formula to N-methyld(-)-isobornylamine and N-methyl-d( + )-bornylamine but having an unspecified steric structure Rubinstein, Pedersen, Fakstorp, and R0nnov-Jessen (1958) to have a weak sympathetic ganglion-blocking activity and to be mildly hypertensive in the anaesthetized cat. A compound with an identical planar formula to N-methylfenchylamine but prepared by an unspecified route was also reported by Rubinstein et al (1958) to have appreciable sympathetic ganglion-blocking activity.…”

Section: Four Structural Isomers Of Mecamylaminementioning

confidence: 99%

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Untitled

1960

British Journal of Pharmacology and Chemotherapy

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The structural requirements for strong ganglion-blocking activity and long duration of action amongst some lower homologues of mecamylamine, together with the discovery of similar activities amongst isomers with enlarged ring structures, are described. In both series of compounds it was found that the successive introduction of C-methyl groups surrounding the nitrogen atom resulted in a progressive increase in ganglion-blocking activity and duration of action.The pharmacology of the potent ganglionblocking compound pempidine, 1,2,2,6,6-pentamethylpiperidine, has recently been described (Corne and Edge, 1958; Spinks, Young, Farrington, and Dunlop, 1958).The independent discovery of the properties of this compound by Spinks and Young (1958) originated from their observation that secondary and tertiary aliphatic amines in which the basic group is sterically hindered by attachment to a tertiary carbon atom have a modest level of ganglion-blocking activity.By contrast, we first studied structure-activity relationships amongst certain aminobicyclo[2,2,1]heptanes which were lower homologues of R=H or alkyl aminobicyclo-[2,2,1]heptanes. N atom is exocyclic bicyclo[3,2,1 ]azaoctanes. N atom is endocyclic mecamylamine. During this work we unexpectedly encountered a chemical route to bicyclo[3,2,1]azaoctanes, isomeric compounds in

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Section: Four Structural Isomers Of Mecamylaminesupporting

confidence: 57%

Section: Four Structural Isomers Of Mecamylaminementioning

confidence: 99%

Untitled

1960

British Journal of Pharmacology and Chemotherapy

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“…The importance of the position of the methyl groups was investigated in a series of six methyl substituted 3-aminonor camphanes (192). Simplification of the molecule led to a series of poly methylcyclohexylamines (182) and to substituted tertiary hexylamines; as a result of this study "penbutamine" [N,N,2,Z,3.pentamethylbutylamine (3)] was found to be equipotent with, and less toxic than mecamylamine (232).…”

Section: Ganglion -Blocking Substancesmentioning

confidence: 98%

Pharmacology of Autonomic Ganglia

Trendelenburg¹

1961

Annu. Rev. Pharmacol.

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“…A compound with an identical planar formula to N-methyld(-)-isobornylamine and N-methyl-d( + )-bornylamine but having an unspecified steric structure Rubinstein, Pedersen, Fakstorp, and R0nnov-Jessen (1958) to have a weak sympathetic ganglion-blocking activity and to be mildly hypertensive in the anaesthetized cat. A compound with an identical planar formula to N-methylfenchylamine but prepared by an unspecified route was also reported by Rubinstein et al (1958) to have appreciable sympathetic ganglion-blocking activity. As our compound was short-acting and that studied by Rubinstein et al was long-acting, it is unlikely that the two were identical chemically.…”

Section: Four Structural Isomers Of Mecamylaminementioning

confidence: 99%

The Ganglion‐blocking Activity of Aminobicyclo‐[2,2, 1]heptanes (Congeners of Mecamylamine) and Bicyclo[3,2, 1]azaoctanes (Bridged Congeners of Pempidine)

Edge

Corne

Lee

et al. 1960

British Journal of Pharmacology and Chemotherapy

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The structural requirements for strong ganglion‐blocking activity and long duration of action amongst some lower homologues of mecamylamine, together with the discovery of similar activities amongst isomers with enlarged ring structures, are described. In both series of compounds it was found that the successive introduction of C‐methyl groups surrounding the nitrogen atom resulted in a progressive increase in ganglion‐blocking activity and duration of action.

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Hypotensive and Ganglion blocking action of methyl substituted 3-amino-norcamphanes

Cited by 13 publications

References 3 publications

Untitled

Untitled

Pharmacology of Autonomic Ganglia

The Ganglion‐blocking Activity of Aminobicyclo‐[2,2, 1]heptanes (Congeners of Mecamylamine) and Bicyclo[3,2, 1]azaoctanes (Bridged Congeners of Pempidine)

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