• Name

  lupanine

• EINECS
• CAS No. 550-90-3
• Article Data18
• CAS DataBase
• Density 1.16g/cm³
• Solubility
• Melting Point 40-44°
• Formula C15H24 N2 O
• Boiling Point 396.7°Cat760mmHg
• Molecular Weight 248.368
• Flash Point 172.7°C
• Transport Information
• Appearance
• Safety Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NO_x.
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 7,14-Methano-2H,11H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one,dodecahydro-, [7S-(7a,7aa,14a,14ab)]-; Lupanine (8CI); Lupanine, d- (6CI); (+)-2-Oxosparteine; (+)-Lupanine;2-Oxosparteine; 7,14-Methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one,dodecahydro-, [7S-(7a,7ab,14a,14aa)]-; Lupanin; d-Lupanine
• PSA 23.55000
• LogP 1.74750

Synthetic route

(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadec-12-en-6-one

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 2.5h;	93%

L-(-)-lupanine D-tartrate salt

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With potassium hydroxide In water	30%

D-(+)-lupanine-L-tartrate

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With potassium hydroxide In water	19%

3019-47-4, 74183-21-4, 74183-22-5, 133163-04-9

lupanine N(16)-oxide

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With sodium tetrahydroborate; formic acid; sulfur dioxide Ambient temperature; other N-oxides of sparteine lactams;
With hydrogen; platinum(IV) oxide In acetic acid under 760 Torr; for 1h; Product distribution; other N-oxides of sparteine lactams; other times;

3019-47-4, 74183-21-4, 74183-22-5, 133163-04-9

lupanine N(16)-oxide

A

17-hydroxylupanine

B

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With formic acid; sulfur dioxide for 0.5h; Mechanism; Product distribution; Ambient temperature; other N-oxides of sparteine lactams; other times;

32101-29-4

5,6-dehydrolupanine

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	3.2 mg
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature;

(+)-lupanine N-oxide

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With sulfur dioxide In methanol at 0℃; for 0.25h;	4 mg

10034-85-2

hydrogen iodide

15358-48-2

13α-hydroxylupanine

red phosphorus

red phosphorus

550-90-3

(+)-lupanine

...Expand

15358-48-2

13α-hydroxylupanine

phosphorus pentoxide

phosphorus pentoxide

A

7732-18-5

water

B

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
at 170℃; folgende Hydrierung;

...Expand

6β-hydroxylupanine

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CHCl3 / 12 h / Ambient temperature 2: 3.2 mg / H2 / 5percent Pd-C / ethanol View Scheme

(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadec-12-en-6-one

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 2.5h;	93%

L-(-)-lupanine D-tartrate salt

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With potassium hydroxide In water	30%

D-(+)-lupanine-L-tartrate

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With potassium hydroxide In water	19%

3019-47-4, 74183-21-4, 74183-22-5, 133163-04-9

lupanine N(16)-oxide

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With sodium tetrahydroborate; formic acid; sulfur dioxide Ambient temperature; other N-oxides of sparteine lactams;
With hydrogen; platinum(IV) oxide In acetic acid under 760 Torr; for 1h; Product distribution; other N-oxides of sparteine lactams; other times;

3019-47-4, 74183-21-4, 74183-22-5, 133163-04-9

lupanine N(16)-oxide

A

17-hydroxylupanine

B

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With formic acid; sulfur dioxide for 0.5h; Mechanism; Product distribution; Ambient temperature; other N-oxides of sparteine lactams; other times;

32101-29-4

5,6-dehydrolupanine

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	3.2 mg
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature;

(+)-lupanine N-oxide

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
With sulfur dioxide In methanol at 0℃; for 0.25h;	4 mg

10034-85-2

hydrogen iodide

15358-48-2

13α-hydroxylupanine

red phosphorus

red phosphorus

550-90-3

(+)-lupanine

...Expand

15358-48-2

13α-hydroxylupanine

phosphorus pentoxide

phosphorus pentoxide

A

7732-18-5

water

B

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
at 170℃; folgende Hydrierung;

...Expand

6β-hydroxylupanine

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CHCl3 / 12 h / Ambient temperature 2: 3.2 mg / H2 / 5percent Pd-C / ethanol View Scheme

17026-42-5

O,O'-dibenzoyl-D-tartaric acid

4356-43-8

rac-lupanine

A

1335287-92-7

(-)-lupanine (+)-2,3-dibenzoyl-D-tartarate

B

550-90-3

(+)-lupanine

C

486-88-4

L-(-)-lupanine

Conditions

Conditions	Yield
In methanol Resolution of racemate; Heating; optical yield given as %ee;

...Expand

87-69-4

L-Tartaric acid

4356-43-8

rac-lupanine

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
Stage #1: L-Tartaric acid; rac-lupanine In acetone Resolution of racemate; Stage #2: With potassium hydroxide In water Resolution of racemate;	n/a

6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one

550-90-3

(+)-lupanine

Conditions

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine; dmap / dichloromethane / 20 h 2.1: triethylamine / tetrahydrofuran / 5 h / 20 °C 3.1: Adam’s catalyst; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr 4.1: sodium tetrahydroborate / 2.5 h / 0 °C 4.2: 4 h / 0 - 20 °C 5.1: boron trifluoride diethyl etherate / dichloromethane / 17 h / 0 - 20 °C 6.1: triethylamine / dichloromethane / 120 h 7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux 8.1: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C / 760.05 Torr View Scheme

3-tert-butoxycarbonyl-6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one

550-90-3

(+)-lupanine

Conditions

Conditions

Yield

Multi-step reaction with 7 steps 1.1: triethylamine / tetrahydrofuran / 5 h / 20 °C 2.1: Adam’s catalyst; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr 3.1: sodium tetrahydroborate / 2.5 h / 0 °C 3.2: 4 h / 0 - 20 °C 4.1: boron trifluoride diethyl etherate / dichloromethane / 17 h / 0 - 20 °C 5.1: triethylamine / dichloromethane / 120 h 6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux 7.1: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C / 760.05 Torr View Scheme

11-tert-butoxycarbonyl-7,11-diazatricyclo[7.3.1.02,7]tridec-2,4-dien-6,10-dione

550-90-3

(+)-lupanine

Conditions

Conditions

Yield

Multi-step reaction with 6 steps 1.1: Adam’s catalyst; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr 2.1: sodium tetrahydroborate / 2.5 h / 0 °C 2.2: 4 h / 0 - 20 °C 3.1: boron trifluoride diethyl etherate / dichloromethane / 17 h / 0 - 20 °C 4.1: triethylamine / dichloromethane / 120 h 5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux 6.1: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C / 760.05 Torr View Scheme

(1S,2R,9S)-11-tert-butoxycarbonyl-7,11-diazatricyclo[7.3.1.02,7]tridecane-6,10-dione

550-90-3

(+)-lupanine

Conditions

Conditions

Yield

Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate / 2.5 h / 0 °C 1.2: 4 h / 0 - 20 °C 2.1: boron trifluoride diethyl etherate / dichloromethane / 17 h / 0 - 20 °C 3.1: triethylamine / dichloromethane / 120 h 4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux 5.1: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C / 760.05 Torr View Scheme

(1S,2R,9S)-11-tert-butoxycarbonyl-10-methoxy-7,11-diazatricyclo[7.3.1.02,7]tridecane-6-one

550-90-3

(+)-lupanine

Conditions

Conditions

Yield

Multi-step reaction with 4 steps 1: boron trifluoride diethyl etherate / dichloromethane / 17 h / 0 - 20 °C 2: triethylamine / dichloromethane / 120 h 3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux 4: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C / 760.05 Torr View Scheme

550-43-6

(-)-Angustifoline

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 120 h 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux 3: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C / 760.05 Torr View Scheme

(1S,2R,9S,10S)-10,11-diallyl-7,11-diazatricyclo[7.3.1.02,7]tridecane-6-one

550-90-3

(+)-lupanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux 2: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C / 760.05 Torr View Scheme

550-90-3

(+)-lupanine

3019-47-4, 74183-21-4, 74183-22-5, 133163-04-9

lupanine N(16)-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 48h;	90%

550-90-3

(+)-lupanine

90-39-1

(-)-sparteine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;	85%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18h; Reflux;	84%
With hydrogenchloride; platinum Hydrogenation;
With lithium aluminium tetrahydride In diethyl ether for 5h; Heating;

550-90-3

(+)-lupanine

(+)-lupanine N-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane	80%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 6h; Ambient temperature;	71%

506-68-3

bromocyane

550-90-3

(+)-lupanine

2584-20-5

(1S)-4c-(4-bromo-butyl)-8-oxo-(11ac)-octahydro-1r,5c-methano-pyrido[1,2-a][1,5]diazocine-3-carbonitrile

Conditions

Conditions	Yield
With benzene

550-90-3

(+)-lupanine

74-88-4

methyl iodide

6080-95-1, 54815-53-1, 58846-15-4, 82978-45-8, 82978-46-9, 115113-81-0

N-16-methyl-2-oxosparteine iodide

Conditions

Conditions	Yield
at 110 - 120℃; im Rohr;
for 96h; Ambient temperature; Yield given;

550-90-3

(+)-lupanine

(+)-2-Thionosparteine

Conditions

Conditions	Yield
With tetraphosphorus decasulfide; potassium polysulfide; xylene

550-90-3

(+)-lupanine

15043-17-1, 55732-48-4, 69427-33-4, 127515-92-8

17-hydroxylupanine

Conditions

Conditions	Yield
With N-Bromosuccinimide; chloroform und anschliessenden Behandeln mit wss.NaOH;
With methanol; silver(l) oxide
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane

550-90-3

(+)-lupanine

(7S)-3,3-dichloro-(7at,14ac)-dodecahydro-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocin-4-one

Conditions

Conditions	Yield
With phosphorus pentachloride anschliessend Behandeln mit Eis;

550-90-3

(+)-lupanine

4697-83-0

(+)-2,17-dioxosparteine

Conditions

Conditions	Yield
With potassium permanganate; acetic acid; acetone
With sodium hydroxide; potassium hexacyanoferrate(III)

550-90-3

(+)-lupanine

15333-74-1, 33964-84-0, 117895-46-2

4-((1S)-(11at)-decahydro-1r,5c-methano-pyrido[1,2-a][1,5]diazocin-4t-yl)-butyric acid ; dihydrochloride

Conditions

Conditions	Yield
With hydrogenchloride
With hydrogenchloride

865-50-9

iodomethane-d3

550-90-3

(+)-lupanine

C16H24(2)H3N2O(1+)*I(1-)

Conditions

Conditions	Yield
In acetone for 72h;

550-90-3

(+)-lupanine

4697-83-0, 38485-03-9

(+)-2,17-dioxosparteine

Conditions

Conditions	Yield
With potassium permanganate

550-90-3

(+)-lupanine

19879-75-5, 20210-08-6, 20210-10-0

(2,2-2H2)sparteine

Conditions

Conditions	Yield
With lithium aluminium deuteride In tetrahydrofuran for 1h; Heating;	50 mg

100-39-0

benzyl bromide

550-90-3

(+)-lupanine

(+)-lupanine-bromobenzylate

(+)-lupanine-bromobenzylate

75-03-6

ethyl iodide

550-90-3

(+)-lupanine

(+)-lupanine hydriodide

(+)-lupanine hydriodide

64-17-5

ethanol

75-03-6

ethyl iodide

550-90-3

(+)-lupanine

(+)-lupanine hydriodide

(+)-lupanine hydriodide

...Expand

100-44-7

benzyl chloride

550-90-3

(+)-lupanine

(+)-lupanine hydrochloride

(+)-lupanine hydrochloride

550-90-3

(+)-lupanine

74-88-4

methyl iodide

(+)-lupanine iodomethylate

(+)-lupanine iodomethylate

Lupanine Chemical Properties

Lupanine Toxicity Data With Reference

Lupanine Safety Profile