Tag: isoquinolines

structural tables; isoquinolines

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A Tabular Key to the structural formula of the cactus isoquinolines

The following includes some isoquinolines that do not occur in cacti;
these are included for structural comparative purposes

Abbreviations are summarized at the end of the table.
An alphabetical listing is also located at the end of this table.
For synonyms please see the index and alkaloid crosslist.
Formyl & Acetyl compounds are not included in this table.

A generic structural diagram is above

 

 

Compound R5 R6 R7 R8     R1  R2a  R2b  R4  unsat
 mono-ring-substituted
 1.  Longimammatine
H MeO H H H
H		 H na H na
 2.  Weberidine
H H MeO H H
H		 H na H na
 3.  Longimammosine
H HO H H H
H		 Me na H na
 4.  Longimammidine
H H H HO H
H		 Me na H na
 5.  ?-Mono-MeO-1-Me-THIQ  (via MIKES)
MeO (position?) Me H na H na
 6.  Longimammamine
H H H HO H
H		 Me na HO na
 7.  Arizonine
H H H MeO HO
H		 Me na H na
 di-ring-substituted
 8.  Heliamine
H MeO MeO H H
H		 H na H na
 9.  Dehydroheliamine
H MeO MeO H H H na H 1,2
 10.  Backebergine
H MeO MeO H H H na H 1,23,4
 11.  Lemaireocereine
H H MeO MeO H
H		 H na H na
 12.  Dehydrolemaireocereine
H H MeO MeO H H na H 1,2
 13.  Isobackebergine
H H MeO MeO H H na H 1,23,4
 14.  Uberine
MeO H HO H H
H		 Me na H na
 15.  Corypalline
H MeO HO H H
H		 Me na H na
 16.  Salsolinol*
H HO HO H Me H na H na
 17.  Salsoline
H HO MeO H Me H na H na
 18.  Isosalsoline
H MeO HO H Me H na H na
 19.  Salsolidine
H MeO MeO H Me H na H na
 20.  Dehydrosalsolidine
H MeO MeO H Me H na H 1,2
 21.  N-Methylheliamine
H MeO MeO H H Me na H na
 22.  Hydrohydrastinine*
  H -O-CH-O- H H
H		 Me na H na
 23.  N-Methylisosalsoline
H MeO HO H Me Me na H na
 24.  Lophocereine
H MeO HO H i-butyl Me na H na
 25.  Carnegine
H MeO MeO H Me Me na H na
 26.  Tepenine
H H MeO MeO Me Me na H na
Compound R5 R6 R7 R8 R1 R2a R2b R4 unsat
 27.  Calycotomine*
  H MeO MeO H -MeOH H na H na
 28.  Isosalsolidine
H MeO MeO H Me H na H 1,23,4
 29.  Dehydrosalsolidine
H MeO MeO H Me H na H 1,2
 tri-ring-substituted
 30.  Hydrocotarnine
  H -O-Me-O- MeO Me Me na H na
 31.  Anhalamine
H MeO MeO HO H H na H na
 32.  Isoanhalamine
H HO MeO MeO H H na H na
 33.  Anhalinine
H MeO MeO MeO H H na H na
 34.  Nortehuanine
MeO MeO MeO H H H na H na
 35.  Anhalidine
H MeO MeO HO H Me na H na
 36.  Isoanhalidine
H HO MeO MeO H Me na H na
 37.  Anhalonine
H MeO -O-Me-O- Me H na H na
 38.  Anhalonidine
H MeO MeO HO Me H na H na
 39.  Isoanhalonidine
H HO MeO MeO Me H na H na
 40.  Lophophorine
H MeO -O-Me-O- Me Me na H na
 41.  O-Methylanhalonidine
H MeO MeO MeO Me H na H na
 42.  Tehuanine
MeO MeO MeO H H Me na H na
 43.  Tehuanine-N-oxide
MeO MeO MeO H H Me →O H na
 44.  Gigantine
HO MeO MeO na na Me Me na na
     Incorrect proposal
(earlier) HO H MeO MeO MeO MeO H H Me
 45.  Pellotine
H MeO MeO HO Me Me na H na
 46.  Isopellotine
H HO MeO MeO Me Me na H 3,4
 47.  O-Methylpellotine
H MeO MeO MeO Me Me na H na
 48.  Pterocereine
glucose-O- MeO MeO H -MeOH Me na H na
 49.  Deglucopterocereine
HO MeO MeO H -MeOH Me na H na
 50.  Deglucopterocereine-N-oxide
HO MeO MeO H -MeOH Me →O H na
 51.  Anhalotine (isolated as Iodide)
H MeO MeO HO H Me I H na
 52.  Lophotine (isolated as Iodide)
H MeO -O-Me-O- Me Me I H na
 53.  Peyotine (isolated as Iodide)
H MeO MeO MeO Me Me I H na
 54.  3,4-Dihydro-6,7-diMeO-8-OH-IQ inner salt
H MeO MeO HO H H na H 1,2
Compound R5 R6 R7 R8 R1 R2a R2b R4 unsat
 55.  3,4-Dihydro-6,7-diMeO-8-OH-2-Me-isoquinolinium inner salt
H MeO MeO O– H Me+ na H 1,2
 56.  3,4-Dihydro-6,7-diMeO-8-OH-1-Me-isoquinoline
H MeO MeO HO Me H na H 1,2
 57.  3,4-Dihydro-6,7-diMeO-8-OH-1,2-diMe-isoquinolinium inner salt
H MeO MeO O– Me Me+ na H 1,2
 58.  Pycnarrhine*
  H MeO HO H H Me+HO– na H 1,2
 59.  N-Methyl-6,7-dimethoxy-isoquinolinium chloride*
  H MeO MeO H H Me+Cl– na H 1,2
 60.  Peyoglutam
H MeO MeO HO  -CH2-CH2-C(O)- na H na
 61.  Mescalotam
H MeO MeO MeO  -CH2-CH2-C(O)- na H na
 62.  Peyoxylic acid
H MeO MeO HO -CO2H H na H na
 63.  O-Methyl-peyoxylic acid
H MeO MeO MeO -CO2H H na H na
 64.  Peyoruvic acid
H MeO MeO HO -Me-CO2H H na H na
 65.  O-Methylpeyoruvic acid
H MeO MeO MeO -Me-CO2H H na H na
 66.  Isonortehuanine
MeO MeO MeO H H H na H 1,23,4
 67.  Dehydronortehuanine
MeO MeO MeO H H H na H 1,2
 68.  Peyophorine
H MeO -O-Me-O- Me Et na H na
 tetra-ring-substituted
 69.  ?-Mono-OH-tri-MeO-2-Me-THIQ (via MIKES)
(MeO)3 & OH (positions?) H Me na H 1,23,4
 70.  ?-Tri-MeO-1-Me-1,2,3,4-tetrahydro-IQ (via MIKES)
(MeO)3 (positions?) Me H na H 1,23,4
 71.  ?-Tri-MeO-1-Me-1,2-dihydro-IQ (via MIKES)
 (MeO)3 (positions?) Me H na H  1,2
 72.  Norweberine
 MeO  MeO  MeO  MeO H H na H na
 73.  Dehydronorweberine
MeO MeO MeO MeO H H na H 1,2
 74.  Isonorweberine
MeO MeO MeO MeO H H na H 1,23,4
 75.  Pachycereine
MeO MeO MeO MeO Me H na H na
 76.  Dehydropachycereine
MeO MeO MeO MeO Me H na H 1,2
 77.  Isopachycereine
MeO MeO MeO MeO Me H na H 1,23,4
 78.  Weberine
MeO MeO MeO MeO H Me na H na
 79.  N-Methylpachycereine
MeO MeO MeO MeO Me Me na H na
 trimeric
 80.  Pilocereine
HHH MeOMeOMeO HOXOYO XYH i-butyli-butyli-butyl MeMeMe nanana HHH nanana
Isoquinoline key: Abbreviations 
1,2: 1,2-Dehydro na: Not applicable
3,4: 3,4-Dehydro HO: Hydroxy
CO2H: Carbonyl -O-Me-O-: Methylenedioxy
H: Hydrogen unsat: Unsaturated.i.e double bond existsbetween 2 numbered carbons.
Me: Methyl X: Point of attachment (X-X)
MeO: Methoxy Y: Point of attachment (Y-Y)
* Not reported as a cactus alkaloid; included for structural comparison
 

Isoquinolines from structural table listed in alphabetical order
Name List #
?-Mono-MeO-1-Methyl-THIQ 5
?-Mono-OH-tri-MeO-2-Methyl-THIQ 69
?-Tri-MeO-1-Methyl-1,2,3,4-dehydro-isoquinoline 70
?-Tri-MeO-1-Methyl-1,2-dehydro-isoquinoline 71
3,4-Dihydro-6,7-dimethoxy-8-hydroxy-1,2-dimethyl-isoquinolinium inner salt 57
3,4-Dihydro-6,7-dimethoxy-8-hydroxy-1-methyl-isoquinoline 56
3,4-Dihydro-6,7-dimethoxy-8-hydroxy-2-methyl-isoquinolinium
inner salt		 55
3,4-Dihydro-6,7-dimethoxy-8-hydroxy-isoquinolin 54
Anhalamine 31
Anhalamine, Iso- 32
Anhalidine 35
Anhalidine, Iso- 36
Anhalinine 33
Anhalonidine 38
Anhalonidine, Iso- 39
Anhalonidine, O-Methyl- 41
Anhalonine 37
Anhalotine (Iodide) 51
Arizonine 7
Backebergine 10
Backebergine, Iso- 13
Calycotomine 27
Carnegine 25
Corypalline 15
Corypalline, O-Methyl- 21
Deglucopterocereine 49
Deglucopterocereine-N-oxide 50
Dehydroheliamine 9
Dehydro-lemaireocereine 12
Dehydronortehuanine 67
Dehydronorweberine 73
Dehydropachycereine 76
Dehydrosalsolidine 20
Dehydrosalsolidine 29
Gigantin 44
Heliamine 8
Heliamine, Dehydro- 9
Heliamine, N-Methyl- 21
Hydrocotarnine 30
Hydrohydrastinine 22
Isoanhalamine 32
Isoanhalidine 36
Isoanhalonidine 39
Isobackebergine 13
Isonortehuanine 66
Isonorweberine 74
Isopachycereine 77
Isopellotine 46
Isosalsolidine 28
Isosalsoline 18
Isosalsoline, N-Methyl- 23
Lemaireocerein 11
Lemaireocereine, Dehydro- 12
Longimammamine 6
Longimammatine 1
Longimammidine 4
Longimammosine 3
Lophocerein 24
Lophophorine 40
Lophotine (Iodide) 52
Mescalotam 61
N-Methyl-6,7-dimethoxy-isoquinolinium chloride 59
N-Methylheliamine 21
N-Methylisosalsoline 23
N-Methyl-pachycereine 79
Nortehuanine 34
Nortehuanine, Dehydro- 67
Nortehuanine, Iso- 66
Norweberine 72
Norweberine, Dehydro- 73
Norweberine, Iso- 74
O-Methyl-anhalonidine 41
O-Methylcorypalline 21
O-Methylpellotine 47
O-Methylpeyoruvic acid 65
O-Methylpeyoxylic acid 63
Pachycereine 75
Pachycereine, Dehydro- 76
Pachycereine, Iso- 77
Pachycereine, N-Methyl- 79
Pellotine 45
Pellotine, Iso- 46
Pellotine, O-Methyl- 47
Peyoglutam 60
Peyophorine 68
Peyoruvic acid 64
Peyoruvic acid, O-Methyl- 65
Peyotine (Iodide) 53
Peyoxylic acid 62
Peyoxylic acid, O-Methyl- 63
Pilocereine 80
Pterocereine 48
Pterocereine, Degluco- 49
Pycnarrhine 58
Salsolidine 19
Salsolidine, Dehydro- 20
Salsolidine, Dehydro- 29
Salsolidine, Iso- 28
Salsoline 17
Salsoline, Iso- 18
Salsoline, N-Methyl-iso- 23
Salsolinol 16
Tehuanine 42
Tehuanine, Dehydronor 67
Tehuanine, Isonor- 66
Tehuanine, Nor- 34
Tehuanine-N-oxide 43
Tepenine 26
Uberine 14
Weberidine 2
Weberine 78
Weberine, Dehydro-nor- 73
Weberine, Isonor- 74
Weberine, Nor- 72