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Name	ELYMOCLAVINE	EINECS	N/A
CAS No.	548-43-6	Density	1.247g/cm³
PSA	39.26000	LogP	1.97820
Solubility	N/A	Melting Point	251°C (rough estimate)
Formula	C16H18 N2 O	Boiling Point	468°Cat760mmHg
Molecular Weight	254.332	Flash Point	236.8°C
Transport Information	N/A	Appearance	N/A
Safety	A poison by intraperitoneal and intravenous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and fumes. See also N,N-DIETHYLLYSERGAMIDE (LSD).	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	Elymoclavine(6CI); D-8,9-Didehydro-6-methylergoline-8-methanol; Elymoclavin; NSC 109431	Article Data	9

ELYMOCLAVINE Synthetic route

: 1027016-28-9
(6aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 20℃; for 48h;	95%

: 548-42-5
agroclavine

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
for 168h; fermentative bioconversion by Ca-alginate immibilized cells of submerged cultures of C. fusiformis W1;	90%

: 63-68-3
L-methionine

: 150-97-0, 690-72-2, 17817-88-8, 32451-23-3
D,L-mevalonic acid

: 54-12-6
Trp

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
With phosphate buffer pH 7.3 In water for 48h; Claviceps sp., strain SD58, medium NL 406;

: 487-89-8
Indole-3-carboxaldehyde

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; copper diacetate / 4 h / 110 °C / Inert atmosphere 2: dmap / acetonitrile / 0.5 h / 40 °C 3: ammonium acetate / 2 h / 70 °C 4: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 5: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 6: triethylamine / dichloromethane / 1 h / 0 - 20 °C 7: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 8: hydrogenchloride; zinc / methanol; water / 1 h 9: potassium carbonate / dichloromethane / 20 h / 20 °C 10: triethylamine / dichloromethane / 24 h / 20 °C 11: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 12: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 13: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 13 steps
1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; copper diacetate / 4 h / 110 °C / Inert atmosphere
2: dmap / acetonitrile / 0.5 h / 40 °C
3: ammonium acetate / 2 h / 70 °C
4: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C
5: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C
6: triethylamine / dichloromethane / 1 h / 0 - 20 °C
7: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
8: hydrogenchloride; zinc / methanol; water / 1 h
9: potassium carbonate / dichloromethane / 20 h / 20 °C
10: triethylamine / dichloromethane / 24 h / 20 °C
11: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere
12: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
13: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: 115698-38-9
(E)-methyl 3-(3-formyl-1H-indol-4-yl)acrylate

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: dmap / acetonitrile / 0.5 h / 40 °C 2: ammonium acetate / 2 h / 70 °C 3: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 4: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 5: triethylamine / dichloromethane / 1 h / 0 - 20 °C 6: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 7: hydrogenchloride; zinc / methanol; water / 1 h 8: potassium carbonate / dichloromethane / 20 h / 20 °C 9: triethylamine / dichloromethane / 24 h / 20 °C 10: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 11: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 12: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: dmap / acetonitrile / 0.5 h / 40 °C
2: ammonium acetate / 2 h / 70 °C
3: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C
4: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C
5: triethylamine / dichloromethane / 1 h / 0 - 20 °C
6: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
7: hydrogenchloride; zinc / methanol; water / 1 h
8: potassium carbonate / dichloromethane / 20 h / 20 °C
9: triethylamine / dichloromethane / 24 h / 20 °C
10: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere
11: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
12: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: (E)-tert-butyl 3-formyl-4-(3-methoxy-3-oxoprop-1-en-1-yl)-1H-indole-1-carboxylate

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: ammonium acetate / 2 h / 70 °C 2: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 3: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 4: triethylamine / dichloromethane / 1 h / 0 - 20 °C 5: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 6: hydrogenchloride; zinc / methanol; water / 1 h 7: potassium carbonate / dichloromethane / 20 h / 20 °C 8: triethylamine / dichloromethane / 24 h / 20 °C 9: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 10: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 11: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: ammonium acetate / 2 h / 70 °C
2: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C
3: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C
4: triethylamine / dichloromethane / 1 h / 0 - 20 °C
5: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
6: hydrogenchloride; zinc / methanol; water / 1 h
7: potassium carbonate / dichloromethane / 20 h / 20 °C
8: triethylamine / dichloromethane / 24 h / 20 °C
9: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere
10: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
11: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: C19H20N2O6

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 3: triethylamine / dichloromethane / 1 h / 0 - 20 °C 4: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 5: hydrogenchloride; zinc / methanol; water / 1 h 6: potassium carbonate / dichloromethane / 20 h / 20 °C 7: triethylamine / dichloromethane / 24 h / 20 °C 8: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 9: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 10: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 10 steps
1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C
3: triethylamine / dichloromethane / 1 h / 0 - 20 °C
4: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
5: hydrogenchloride; zinc / methanol; water / 1 h
6: potassium carbonate / dichloromethane / 20 h / 20 °C
7: triethylamine / dichloromethane / 24 h / 20 °C
8: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere
9: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
10: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: C18H22N2O5

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 3: hydrogenchloride; zinc / methanol; water / 1 h 4: potassium carbonate / dichloromethane / 20 h / 20 °C 5: triethylamine / dichloromethane / 24 h / 20 °C 6: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 7: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 8: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
2: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
3: hydrogenchloride; zinc / methanol; water / 1 h
4: potassium carbonate / dichloromethane / 20 h / 20 °C
5: triethylamine / dichloromethane / 24 h / 20 °C
6: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere
7: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
8: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: C20H24N2O6

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 2: hydrogenchloride; zinc / methanol; water / 1 h 3: potassium carbonate / dichloromethane / 20 h / 20 °C 4: triethylamine / dichloromethane / 24 h / 20 °C 5: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 6: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 7: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
2: hydrogenchloride; zinc / methanol; water / 1 h
3: potassium carbonate / dichloromethane / 20 h / 20 °C
4: triethylamine / dichloromethane / 24 h / 20 °C
5: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere
6: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
7: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: C18H20N2O4

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: hydrogenchloride; zinc / methanol; water / 1 h 2: potassium carbonate / dichloromethane / 20 h / 20 °C 3: triethylamine / dichloromethane / 24 h / 20 °C 4: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 6: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: hydrogenchloride; zinc / methanol; water / 1 h
2: potassium carbonate / dichloromethane / 20 h / 20 °C
3: triethylamine / dichloromethane / 24 h / 20 °C
4: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere
5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
6: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

ELYMOCLAVINE Chemical Properties

Molecular Formula:C₁₆H₁₈N₂O
Molecular Weight:254.36
Density:1.247g/cm³
Boiling Point:468°C at 760mmHg
Flash Point:236.8°C
Properties:A solid
Mp: 250–252°C

ELYMOCLAVINE History

A close chemical relative of LSD found in ergot fungi and bindweeds of the genus Ipomoea, Fam. convolvulaceae ( JANSAG Journal of Animal Science. 41 (1975),1700. ).

ELYMOCLAVINE Uses

Elymoclavine soluble in pyridine is sympathetic to stimulate the central role and the central nervous system stimulant. Ergot is by and bindweed Branch silver leaf and flower is a gland vine leaves (Stictocardia tiliaefolia) from the plant alkaloids.

ELYMOCLAVINE Production

Ergot alkaloid isolated from cultures of fungi parasitic on Elymis mollis Trin; toxic alkaloid produced by Claviceps purpurea

ELYMOCLAVINE Safety Profile

Elymoclavine may be a poison by intraperitoneal and intravenous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and fumes.

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