Colchicine supplier | CasNO.64-86-8

Name
Colchicine
EINECS 200-598-5
CAS No. 64-86-8
Article Data23
CAS DataBase
Density 1.25 g/cm³
Solubility 45 g/L (20 °C) in water
Melting Point 150-160 °C (dec.)(lit.)
Formula C₂₂H₂₅NO₆
Boiling Point 726 °C at 760 mmHg
Molecular Weight 399.444
Flash Point 392.9 °C
Transport Information UN 1544 6.1/PG 1
Appearance Yellow solid
Safety 13-45
Risk Codes 26/28
Molecular Structure
Hazard Symbols T, T+
Synonyms Acetamide,N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-;Colchicine (8CI);(-)-Colchicine;(S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide;Colchineos;Colchisol;Colcin;Colsaloid;Condylon;NSC 757;
PSA 83.09000
LogP 3.26250

Synthetic route

: 108-24-7
acetic anhydride

: 186374-95-8
(S)-tert-butyl N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate

: 64-86-8
colchicine

Conditions

Conditions	Yield
Stage #1: (S)-tert-butyl N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate With hydrogenchloride In diethyl ether at 20℃; for 1h; Stage #2: acetic anhydride With dmap; triethylamine In diethyl ether at 25℃; for 10h;	98%

: methoxymagnesium bromide

: 10-demethoxy-10-tosylcolchicine

: 64-86-8
colchicine

Conditions

Conditions	Yield
In tetrahydrofuran for 5h;	85%

: C22H27NO7

: 64-86-8
colchicine

Conditions

Conditions	Yield
With N,N-dimethyl-ethanamine; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 12h; Inert atmosphere;	81%
With N,N-dimethyl-ethanamine; trimethylsilyl trifluoromethanesulfonate In dichloromethane	81%
With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at 20℃; for 2h;	75%

: 109-88-6, 16436-83-2, 16436-85-4
magnesium methanolate

: 10-demethoxy-10-tosylcolchicine

: 64-86-8
colchicine

Conditions

Conditions	Yield
In methanol	78%

: 186581-53-3, 908094-01-9
diazomethane

: 60-29-7
diethyl ether

: 67-66-3
chloroform

: 477-27-0, 1990-46-1
colchiceine

A: 64-86-8
colchicine

B: 518-12-7
(7S)-isocolchicine

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 477-27-0, 1990-46-1
colchiceine

A: 64-86-8
colchicine

B: 518-12-7
(7S)-isocolchicine

Conditions

Conditions	Yield
With diethyl ether; chloroform

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 33530-04-0
2,10-didemethylcolchicine

A: 64-86-8
colchicine

B: 7336-36-9
2-demethylcolchicine

C: 518-12-7
(7S)-isocolchicine

D: 142713-50-6
2-demethylisocolchicine

Conditions

Conditions	Yield
In diethyl ether; chloroform

...Expand

: 133946-40-4
<1-3H>-3-phenylpropanal

: 64-86-8
colchicine

Conditions

Conditions	Yield
Colchicum byzantinum biosynthesis;

: 4469-06-1
<3-14C>-cinnamic acid

: 64-86-8
colchicine

Conditions

Conditions	Yield
Colchicum byzantinum biosynthesis;

: 3476-50-4
deacetylcolchicine

: 108-24-7
acetic anhydride

: 64-86-8
colchicine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In chloroform; water for 2.5h;
Acetylation;

: 133946-39-1
<1-3H>-3-phenylprop-2-enal

: 64-86-8
colchicine

Conditions

Conditions	Yield
Colchicum byzantinum biosynthesis;

: 131946-50-4
<3-14C>-3-phenylpropionic acid

: 64-86-8
colchicine

Conditions

Conditions	Yield
Colchicum byzantinum biosynthesis;

: 13744-69-9
DL-phenylalanine

: 64-86-8
colchicine

Conditions

Conditions	Yield
Colchicum byzantinum biosynthesis;

: colchicine-β-cyclodextrin complex

A: 64-86-8
colchicine

B: 7585-39-9
β‐cyclodextrin

Conditions

Conditions	Yield
at 25 - 60℃; Equilibrium constant;

: 186581-53-3, 908094-01-9
diazomethane

(-)-O2-demethyl-colchicine: (-)-O2-demethyl-colchicine

: 64-86-8
colchicine

Conditions

Conditions	Yield
With methanol; diethyl ether

: 186581-53-3, 908094-01-9
diazomethane

(-)-O3-demethyl-colchicine: (-)-O3-demethyl-colchicine

: 64-86-8
colchicine

Conditions

Conditions	Yield
With methanol; diethyl ether

: 53560-26-2
3-(3,4,5-trimethoxyphenyl)propan-1-ol

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 17 steps 1.1: 98 percent / 2,6-lutidine / CH2Cl2 / 5 h / 20 °C 2.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C 3.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C 4.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C 5.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 6.1: BH3THF / tetrahydrofuran / 1 h / 20 °C 6.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 6.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 7.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 8.1: 85 percent / BH3THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 9.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 10.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 11.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 12.1: 60 percent / various solvent(s) / 66 h / Heating 13.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 14.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 15.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 16.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 17.1: HCl / diethyl ether / 1 h / 20 °C 17.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 18 steps 1: 2,6-lutidine 2: I2; CF3CO2Ag / CHCl3 3: Et2NH; CuI / (Ph3P)2PdCl2 / dimethylsulfoxide 4: TBAF / tetrahydrofuran 5: (COCl)2; DMSO; Et3N 7: (COCl)2; DMSO; Et3N 9: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 10: Ph3P; H2O 11: Et3N 12: 70 percent / 1,2-dichloro-benzene / Heating 13: LiOH 15: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 16: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 17: HCl View Scheme

Yield

Multi-step reaction with 17 steps
1.1: 98 percent / 2,6-lutidine / CH2Cl2 / 5 h / 20 °C
2.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C
3.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C
4.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C
5.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C
6.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C
6.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C
6.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C
7.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C
8.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C
9.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
10.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
11.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
12.1: 60 percent / various solvent(s) / 66 h / Heating
13.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
14.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
15.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
16.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
17.1: HCl / diethyl ether / 1 h / 20 °C
17.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 18 steps
1: 2,6-lutidine
2: I2; CF3CO2Ag / CHCl3
3: Et2NH; CuI / (Ph3P)2PdCl2 / dimethylsulfoxide
4: TBAF / tetrahydrofuran
5: (COCl)2; DMSO; Et3N
7: (COCl)2; DMSO; Et3N
9: 64 percent / PPh3; DEAD; (PhO)2P(O)N3
10: Ph3P; H2O
11: Et3N
12: 70 percent / 1,2-dichloro-benzene / Heating
13: LiOH
15: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
16: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
17: HCl
View Scheme

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: zinc-copper couple / benzene; N,N-dimethyl-acetamide / 3 h / 20 °C / sonication 1.2: 31 percent / bis(triphenylphosphine)palladium dichloride / benzene; N,N-dimethyl-acetamide / 2 h / sonication 2.1: 91 percent / H2 / Pd/C / ethanol; H2O / 22 h / 3102.89 Torr 3.1: 93 percent / NaHCO3; silver trifluoroacetate; I2 / CHCl3 / 2 h / 0 °C 4.1: trifluoroacetic acid / diethyl ether / 3 h / 20 °C 5.1: 454 mg / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h 6.1: 60 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C 7.1: 91 percent / potassium carbonate / methanol / 11 h / 20 °C 8.1: 100 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C 9.1: potassium carbonate / methanol / 1 h / Heating 9.2: 64 percent / KOH / methanol / 3 h / Heating 10.1: 70 percent / various solvent(s) / 40 h / Heating 11.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 12.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 13.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 14.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 15.1: HCl / diethyl ether / 1 h / 20 °C 15.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

Yield

Multi-step reaction with 15 steps
1.1: zinc-copper couple / benzene; N,N-dimethyl-acetamide / 3 h / 20 °C / sonication
1.2: 31 percent / bis(triphenylphosphine)palladium dichloride / benzene; N,N-dimethyl-acetamide / 2 h / sonication
2.1: 91 percent / H2 / Pd/C / ethanol; H2O / 22 h / 3102.89 Torr
3.1: 93 percent / NaHCO3; silver trifluoroacetate; I2 / CHCl3 / 2 h / 0 °C
4.1: trifluoroacetic acid / diethyl ether / 3 h / 20 °C
5.1: 454 mg / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h
6.1: 60 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C
7.1: 91 percent / potassium carbonate / methanol / 11 h / 20 °C
8.1: 100 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C
9.1: potassium carbonate / methanol / 1 h / Heating
9.2: 64 percent / KOH / methanol / 3 h / Heating
10.1: 70 percent / various solvent(s) / 40 h / Heating
11.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
12.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
13.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
14.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
15.1: HCl / diethyl ether / 1 h / 20 °C
15.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

: 327024-99-7
3-(2-ethynyl-3,4,5-trimethoxy-phenyl)-propionaldehyde

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: BH3THF / tetrahydrofuran / 1 h / 20 °C 1.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 1.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 2.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 3.1: 85 percent / BH3THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 4.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 5.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 6.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 7.1: 60 percent / various solvent(s) / 66 h / Heating 8.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 9.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 10.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 11.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 12.1: HCl / diethyl ether / 1 h / 20 °C 12.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 13 steps 2: (COCl)2; DMSO; Et3N 4: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 5: Ph3P; H2O 6: Et3N 7: 70 percent / 1,2-dichloro-benzene / Heating 8: LiOH 10: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 11: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 12: HCl View Scheme

Yield

Multi-step reaction with 12 steps
1.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C
1.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C
1.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C
2.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C
3.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C
4.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
5.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
6.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
7.1: 60 percent / various solvent(s) / 66 h / Heating
8.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
9.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
10.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
11.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
12.1: HCl / diethyl ether / 1 h / 20 °C
12.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 13 steps
2: (COCl)2; DMSO; Et3N
4: 64 percent / PPh3; DEAD; (PhO)2P(O)N3
5: Ph3P; H2O
6: Et3N
7: 70 percent / 1,2-dichloro-benzene / Heating
8: LiOH
10: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
11: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
12: HCl
View Scheme

: 206195-25-7
3-(2-ethynyl-3,4,5-trimethoxyphenyl)propan-1-ol

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 2.1: BH3THF / tetrahydrofuran / 1 h / 20 °C 2.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 2.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 3.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 4.1: 85 percent / BH3THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 5.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 6.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 7.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 8.1: 60 percent / various solvent(s) / 66 h / Heating 9.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 10.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 11.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 12.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 13.1: HCl / diethyl ether / 1 h / 20 °C 13.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 14 steps 1: (COCl)2; DMSO; Et3N 3: (COCl)2; DMSO; Et3N 5: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 6: Ph3P; H2O 7: Et3N 8: 70 percent / 1,2-dichloro-benzene / Heating 9: LiOH 11: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 12: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 13: HCl View Scheme

Yield

Multi-step reaction with 13 steps
1.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C
2.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C
2.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C
2.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C
3.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C
4.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C
5.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
6.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
7.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
8.1: 60 percent / various solvent(s) / 66 h / Heating
9.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
10.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
11.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
12.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
13.1: HCl / diethyl ether / 1 h / 20 °C
13.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 14 steps
1: (COCl)2; DMSO; Et3N
3: (COCl)2; DMSO; Et3N
5: 64 percent / PPh3; DEAD; (PhO)2P(O)N3
6: Ph3P; H2O
7: Et3N
8: 70 percent / 1,2-dichloro-benzene / Heating
9: LiOH
11: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
12: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
13: HCl
View Scheme

: 3-(2-ethynyl-3,4,5-trimethoxy-phenyl)-1-oxazol-2-yl-propan-1-one

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 2.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 3.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 4.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 5.1: 60 percent / various solvent(s) / 66 h / Heating 6.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 7.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 8.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 9.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 10.1: HCl / diethyl ether / 1 h / 20 °C 10.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 11 steps 2: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 3: Ph3P; H2O 4: Et3N 5: 70 percent / 1,2-dichloro-benzene / Heating 6: LiOH 8: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 9: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 10: HCl View Scheme

Yield

Multi-step reaction with 10 steps
1.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C
2.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
3.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
4.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
5.1: 60 percent / various solvent(s) / 66 h / Heating
6.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
7.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
8.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
9.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
10.1: HCl / diethyl ether / 1 h / 20 °C
10.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 11 steps
2: 64 percent / PPh3; DEAD; (PhO)2P(O)N3
3: Ph3P; H2O
4: Et3N
5: 70 percent / 1,2-dichloro-benzene / Heating
6: LiOH
8: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
9: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
10: HCl
View Scheme

: 206195-28-0
3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(1,3-oxazol-2-yl)propan-1-ol

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 2.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 3.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 4.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 5.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 6.1: 60 percent / various solvent(s) / 66 h / Heating 7.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 8.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 9.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 10.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 11.1: HCl / diethyl ether / 1 h / 20 °C 11.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 12 steps 1: (COCl)2; DMSO; Et3N 3: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 4: Ph3P; H2O 5: Et3N 6: 70 percent / 1,2-dichloro-benzene / Heating 7: LiOH 9: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 10: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 11: HCl View Scheme

Yield

Multi-step reaction with 11 steps
1.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C
2.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C
3.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
4.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
5.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
6.1: 60 percent / various solvent(s) / 66 h / Heating
7.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
8.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
9.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
10.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
11.1: HCl / diethyl ether / 1 h / 20 °C
11.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 12 steps
1: (COCl)2; DMSO; Et3N
3: 64 percent / PPh3; DEAD; (PhO)2P(O)N3
4: Ph3P; H2O
5: Et3N
6: 70 percent / 1,2-dichloro-benzene / Heating
7: LiOH
9: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
10: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
11: HCl
View Scheme

: 327025-17-2
triisopropyl-[3-(3,4,5-trimethoxy-phenyl)-propoxy]-silane

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 16 steps 1.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C 2.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C 3.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C 4.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 5.1: BH3THF / tetrahydrofuran / 1 h / 20 °C 5.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 5.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 6.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 7.1: 85 percent / BH3THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 8.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 9.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 10.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 11.1: 60 percent / various solvent(s) / 66 h / Heating 12.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 13.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 14.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 15.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 16.1: HCl / diethyl ether / 1 h / 20 °C 16.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 17 steps 1: I2; CF3CO2Ag / CHCl3 2: Et2NH; CuI / (Ph3P)2PdCl2 / dimethylsulfoxide 3: TBAF / tetrahydrofuran 4: (COCl)2; DMSO; Et3N 6: (COCl)2; DMSO; Et3N 8: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 9: Ph3P; H2O 10: Et3N 11: 70 percent / 1,2-dichloro-benzene / Heating 12: LiOH 14: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 15: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 16: HCl View Scheme

Yield

Multi-step reaction with 16 steps
1.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C
2.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C
3.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C
4.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C
5.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C
5.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C
5.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C
6.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C
7.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C
8.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
9.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
10.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
11.1: 60 percent / various solvent(s) / 66 h / Heating
12.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
13.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
14.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
15.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
16.1: HCl / diethyl ether / 1 h / 20 °C
16.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 17 steps
1: I2; CF3CO2Ag / CHCl3
2: Et2NH; CuI / (Ph3P)2PdCl2 / dimethylsulfoxide
3: TBAF / tetrahydrofuran
4: (COCl)2; DMSO; Et3N
6: (COCl)2; DMSO; Et3N
8: 64 percent / PPh3; DEAD; (PhO)2P(O)N3
9: Ph3P; H2O
10: Et3N
11: 70 percent / 1,2-dichloro-benzene / Heating
12: LiOH
14: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
15: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
16: HCl
View Scheme

: 206195-32-6
5-[(3S)-3-azido-3-(1,3-oxazol-2-yl)propyl]-4-ethynyl-1,2,3-trimethoxybenzene

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 2.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 3.1: 60 percent / various solvent(s) / 66 h / Heating 4.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 5.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 6.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 7.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 8.1: HCl / diethyl ether / 1 h / 20 °C 8.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 9 steps 1: Ph3P; H2O 2: Et3N 3: 70 percent / 1,2-dichloro-benzene / Heating 4: LiOH 6: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 7: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 8: HCl View Scheme

Yield

Multi-step reaction with 8 steps
1.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
2.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
3.1: 60 percent / various solvent(s) / 66 h / Heating
4.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
5.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
6.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
7.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
8.1: HCl / diethyl ether / 1 h / 20 °C
8.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 9 steps
1: Ph3P; H2O
2: Et3N
3: 70 percent / 1,2-dichloro-benzene / Heating
4: LiOH
6: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
7: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
8: HCl
View Scheme

: 327024-98-6
(S)-3-(2-Ethynyl-3,4,5-trimethoxy-phenyl)-1-oxazol-2-yl-propylamine

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 2.1: 60 percent / various solvent(s) / 66 h / Heating 3.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 4.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 5.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 6.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 7.1: HCl / diethyl ether / 1 h / 20 °C 7.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 8 steps 1: Et3N 2: 70 percent / 1,2-dichloro-benzene / Heating 3: LiOH 5: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 6: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 7: HCl View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
2.1: 60 percent / various solvent(s) / 66 h / Heating
3.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
4.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
5.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
6.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
7.1: HCl / diethyl ether / 1 h / 20 °C
7.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 8 steps
1: Et3N
2: 70 percent / 1,2-dichloro-benzene / Heating
3: LiOH
5: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
6: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
7: HCl
View Scheme

: 206195-30-4
(1R)-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(1,3-oxazol-2-yl)propan-1-ol

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 2.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 3.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 4.1: 60 percent / various solvent(s) / 66 h / Heating 5.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 6.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 7.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 8.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 9.1: HCl / diethyl ether / 1 h / 20 °C 9.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 10 steps 1: 64 percent / PPh3; DEAD; (PhO)2P(O)N3 2: Ph3P; H2O 3: Et3N 4: 70 percent / 1,2-dichloro-benzene / Heating 5: LiOH 7: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 8: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 9: HCl View Scheme

Yield

Multi-step reaction with 9 steps
1.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C
2.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C
3.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C
4.1: 60 percent / various solvent(s) / 66 h / Heating
5.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
6.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
7.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
8.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
9.1: HCl / diethyl ether / 1 h / 20 °C
9.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 10 steps
1: 64 percent / PPh3; DEAD; (PhO)2P(O)N3
2: Ph3P; H2O
3: Et3N
4: 70 percent / 1,2-dichloro-benzene / Heating
5: LiOH
7: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
8: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
9: HCl
View Scheme

: 206195-21-3
(S)-N-7-acetylamino-12,13,14-trimethoxy-5-oxatricyclo[8.4.0.02,6]tetradeca-1(10),2(6),3,11,13-pentaene

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 2.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 3.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 4.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 5.1: HCl / diethyl ether / 1 h / 20 °C 5.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 6 steps 1: LiOH 3: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 4: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 5: HCl View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
2.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
3.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
4.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
5.1: HCl / diethyl ether / 1 h / 20 °C
5.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 6 steps
1: LiOH
3: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
4: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
5: HCl
View Scheme

: 206195-23-5
(S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(2-oxazolyl)-propylamine

: 64-86-8
colchicine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 60 percent / various solvent(s) / 66 h / Heating 2.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 3.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 4.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 5.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 6.1: HCl / diethyl ether / 1 h / 20 °C 6.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme
Multi-step reaction with 7 steps 1: 70 percent / 1,2-dichloro-benzene / Heating 2: LiOH 4: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C 5: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C 6: HCl View Scheme

Yield

Multi-step reaction with 6 steps
1.1: 60 percent / various solvent(s) / 66 h / Heating
2.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C
3.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h
4.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C
5.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C
6.1: HCl / diethyl ether / 1 h / 20 °C
6.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C
View Scheme

Multi-step reaction with 7 steps
1: 70 percent / 1,2-dichloro-benzene / Heating
2: LiOH
4: 45 percent / TMSOTf / various solvent(s) / -78 - -50 °C
5: 62 percent / TMSOTf; Et3N / CH2Cl2 / 0 - 10 °C
6: HCl
View Scheme

: 64-86-8
colchicine

: 3123-89-5
N-[(7S)-1,2,3-trimethoxy-9-oxo-10-amino-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide

Conditions

Conditions	Yield
With ammonium hydroxide In ethanol for 12h; Reflux;	100%
With ammonium hydroxide In methanol at 20℃;	90%
With ammonium hydroxide In ethanol at 110℃; for 0.25h; Microwave irradiation;	75%

: 64-86-8
colchicine

: 6714-14-3
allocolchicinic acid

Conditions

Conditions	Yield
With sodium methylate In methanol at 65℃; for 4h;	100%
With methanol; sodium methylate In water at 65℃;	99%
With methanol; water; sodium methylate

: 4885-02-3
Dichloromethyl methyl ether

: 64-86-8
colchicine

: 2730-82-7
4-Formylcolchicine

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane	100%
With tin(IV) chloride In dichloromethane at 20℃; for 13h; Cooling with ice; Inert atmosphere;	100%
With tin(IV) chloride In dichloromethane 0 deg C, 30 min., r.t. 15 h;	90%
With tin(IV) chloride In dichloromethane at 20℃;

: 24424-99-5
di-tert-butyl dicarbonate

: 64-86-8
colchicine

: 186374-94-7
(S)-tert-butyl-N-acetyl(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate

Conditions

Conditions	Yield
With dmap; triethylamine In acetonitrile at 100℃; for 7.5h;	100%
With dmap; triethylamine In acetonitrile at 100℃; Inert atmosphere;	98%
With dmap; triethylamine In tetrahydrofuran for 2h; Reflux;	97.5%

: 50-00-0
formaldehyd

: 64-86-8
colchicine

: 51-79-6
urethane

: ethyl {[(7S)-7-(acetylamino)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-4-yl]methyl}carbamate

Conditions

Conditions	Yield
Stage #1: formaldehyd; urethane With sulfuric acid; water at 20℃; for 0.166667h; Stage #2: colchicine at 20℃; for 4h;	99%

...Expand

: 64-86-8
colchicine

: 1267993-28-1
4-Bromocolchicine

Conditions

Conditions	Yield
With N-Bromosuccinimide; acetic acid	99%
With N-Bromosuccinimide; acetic acid; trifluoroacetic acid at 20℃; for 1h; Schlenk technique; Inert atmosphere;	95%
With N-Bromosuccinimide; acetic acid; trifluoroacetic acid In trifluoroacetic acid at 20℃; for 1h; Schlenk technique; Inert atmosphere;	95%

: 64-86-8
colchicine

: 1267993-31-6
4-Iodocolchicine

Conditions

Conditions	Yield
With N-iodo-succinimide; acetic acid	99%
With N-iodo-succinimide; acetic acid at 70℃; for 7h; Time; Inert atmosphere;	98.6%
With N-iodo-succinimide; acetic acid In acetonitrile at 70℃; for 20h; Inert atmosphere;	95%
With N-iodo-succinimide; acetic acid at 70℃; for 20h; Inert atmosphere;	95%
With N-iodo-succinimide; acetic acid at 70℃; for 7h;

: 115531-70-9
[(S)-1-(2-aminoethyl)-pyrrolidin-2-yl]methanol

: 64-86-8
colchicine

: 1415569-02-6
C28H37N3O6

Conditions

Conditions	Yield
In dichloromethane at 70℃; for 4h;	99%

: 867008-77-3
[(2R)-1-(2-aminoethyl)pyrrolidin-2-yl]methanol

: 64-86-8
colchicine

: 1415569-03-7
C28H37N3O6

Conditions

Conditions	Yield
In dichloromethane at 70℃; for 4h;	99%

: 64-86-8
colchicine

: 477-27-0, 1990-46-1
colchiceine

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid In water at 100℃; for 3h;	98%
With hydrogenchloride; acetic acid In water at 100℃; for 3h;	98%
With hydrogenchloride; acetic acid at 100℃; for 3h;	98%

: 64-86-8
colchicine

: 141-43-5
ethanolamine

: 55340-40-4
N-[(S)-10-(2-hydroxy-ethylamino)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl]-acetamide

Conditions

Conditions	Yield
In dichloromethane at 70℃; for 4h;	98%
In ethanol at 20℃; for 48h;	90%

: 1002-57-9
8-Aminooctanoic acid

: 64-86-8
colchicine

: C29H38N2O7

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water for 24h;	96%

: 64-86-8
colchicine

: C22H25NO6*Li(1+)

Conditions

Conditions	Yield
With lithium nitrate In methanol at 20℃; for 24h;	96%

: 64-86-8
colchicine

: 5188-07-8
sodium thiomethoxide

: 2730-71-4
thiocolchicine

Conditions

Conditions	Yield
In water for 1h; Heating;	95%
In methanol; water at 20℃; for 72h;	78%
In methanol; water at 20℃; for 72h;	78%

: 64-86-8
colchicine

: 618-39-3
benzamidin

: (S)-N-(5,6,7,8a-tetrahydro-1,2,3-trimethoxy-10-phenylbenzo[6,7]heptaleno[2,3-d]imidazol-7-yl)acetamide

Conditions

Conditions	Yield
In benzene at 20℃; for 24h; Condensation; substitution;	95%

: 64-86-8
colchicine

: 847499-95-0
1-(2-aminoethyl)piperidin-3-ol

: 1415569-00-4
C28H37N3O6

Conditions

Conditions	Yield
In dichloromethane at 70℃; for 4h;	95%

: 64-86-8
colchicine

: 107-15-3
ethylenediamine

: 67620-27-3
(S)-N-(10-((2-aminoethyl)amino)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo [a]heptalen-7-yl acetamide)

Conditions

Conditions	Yield
In dichloromethane at 70℃; for 4h;	95%

: 64-86-8
colchicine

: C22H25NO6*Rb(1+)*I(1-)

Conditions

Conditions	Yield
With rubidium iodide In methanol	95%

: 64-86-8
colchicine

: C22H25NO6*Rb(1+)*ClO4(1-)

Conditions

Conditions	Yield
With rubidium perchlorate In methanol	95%

: 64-86-8
colchicine

: C22H25NO6*Na(1+)*NO3(1-)

Conditions

Conditions	Yield
With sodium nitrate In methanol at 20℃; for 24h;	95%

: 64-86-8
colchicine

: C22H25NO6*K(1+)*NO3(1-)

Conditions

Conditions	Yield
With potassium nitrate In methanol at 20℃; for 24h;	95%

: 64-86-8
colchicine

: 100-46-9
benzylamine

: 76129-15-2
N-<5,6,7,9-tetrahydro-1,2,3-trimethoxy-9-oxo-10-<(phenylmethyl)amino>benzoheptalen-7-yl>-(S)-acetamide

Conditions

Conditions	Yield
In ethanol at 116℃; for 20h;	94%
at 20℃; for 72h;	80%
With ethanol

: 64-86-8
colchicine

: C22H25NO6*Cs(1+)*I(1-)

Conditions

Conditions	Yield
With cesium iodide In methanol	94%

: 64-86-8
colchicine

: C22H25NO6*Mg(2+)*2NO3(1-)

Conditions

Conditions	Yield
With magnesium(II) nitrate In methanol at 20℃; for 24h;	94%

: 64-86-8
colchicine

: 38838-27-6
(aR,5S)-N-(3-hydroxy-2-iodo-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-5-yl)-acetamide

Conditions

Conditions	Yield
Stage #1: colchicine With hydrogenchloride; acetic acid In water at 100℃; for 3h; Stage #2: With iodine; potassium iodide; sodium hydroxide In water at 0 - 5℃; for 1h;	93%
Stage #1: colchicine With hydrogenchloride; acetic acid at 100℃; for 3h; Stage #2: With iodine; potassium iodide; sodium hydroxide In water at 0 - 5℃; for 2h;	91%
Stage #1: colchicine With hydrogenchloride; acetic acid at 100℃; for 3h; Stage #2: With iodine; potassium iodide; sodium hydroxide In water at 0 - 5℃; for 2h;	88%

: 64-86-8
colchicine

: C22H25NO6*Cs(1+)*ClO4(1-)

Conditions

Conditions	Yield
With cesium perchlorate In methanol	93%

: 64-86-8
colchicine

: 109-89-7
diethylamine

: 6962-03-4
N-[(7S)-1,2,3-trimethoxy-9-oxo-10-(diethylamino)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide

Conditions

Conditions	Yield
In dichloromethane; acetonitrile for 24h; Reflux; regioselective reaction;	92%
In ethanol at 20℃; for 48h;	90%
In methanol at 20℃;	75%

: 64-86-8
colchicine

: N-(10-amino-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide

Conditions

Conditions	Yield
With ammonium hydroxide Substitution;	90%

: 64-86-8
colchicine

: 142-84-7
di-n-propylamine

: C27H36N2O5

Conditions

Conditions	Yield
In dichloromethane; acetonitrile for 24h; Reflux; regioselective reaction;	90%

Colchicine Chemical Properties

IUPAC: N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
Molecular Formula:C₂₂H₂₅NO₆
Molecular Weight:399.44
EINECS:200-598-5
Melting Point:150-160 °C (dec.)(lit.)
Solubility: H₂O: 10 mg/mL
Form:Powder
Color:White to yellow with a green cast
Water Solubility:45 g/L (20 °C)
Classification Code: Agricultural Chemical; Antimitotic Agents; Antirheumatic Agents; Drug / Therapeutic Agent; Gout suppressants; Human Data; Mitosis Modulators; Mutation data; Reproductive Effect; Skin / Eye Irritant; Suppressant [gout]; Tubulin Modulators
Index of Refraction: 1.584
Molar Refractivity: 106.6 cm³
Molar Volume: 318.1 cm3
Surface Tension: 50.5 dyne/cm
Density: 1.25 g/cm3
Flash Point: 392.9 °C
Enthalpy of Vaporization: 106.01 kJ/mol
Boiling Point: 726 °C at 760 mmHg
Vapour Pressure of Colchicine (CAS NO.64-86-8): 6.21E-21 mmHg at 25 °C

Colchicine Uses

Colchicine(64-86-8) is used as an antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signal.

Colchicine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	31600ug/kg (31.6mg/kg)		Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat	LD50	intravenous	250ug/kg (0.25mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: NAUSEA OR VOMITING	Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 261, 1952.
cat	LDLo	oral	125ug/kg (0.125mg/kg)		"Principles of Insect Chemosterilization," Labrecque, G.C., and C.N. Smith, eds., New York, Appleton-Century-Crofts, 1968Vol. -, Pg. 315, 1968.
cat	LDLo	subcutaneous	500ug/kg (0.5mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1337, 1935.
child	TDLo	parenteral	2400ug/kg (2.4mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE	Veterinary and Human Toxicology. Vol. 37, Pg. 366, 1995.
dog	LDLo	oral	125ug/kg (0.125mg/kg)		"Principles of Insect Chemosterilization," Labrecque, G.C., and C.N. Smith, eds., New York, Appleton-Century-Crofts, 1968Vol. -, Pg. 315, 1968.
dog	LDLo	subcutaneous	571ug/kg (0.571mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1337, 1935.
dog	LDLo	unreported	5mg/kg (5mg/kg)		Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 27, Pg. 119, 1890.
gerbil	LD50	intraperitoneal	90mg/kg (90mg/kg)		Medicina et Pharmacologia Experimentalis. Vol. 17, Pg. 323, 1967.
guinea pig	LD50	intraperitoneal	500ug/kg (0.5mg/kg)		Medicina Experimentalis. Vol. 6, Pg. 101, 1962.
guinea pig	LDLo	oral	12500ug/kg (12.5mg/kg)	LIVER: OTHER CHANGES BLOOD: CHANGES IN SPLEEN BLOOD: OTHER CHANGES	Virchows Archiv fuer Pathologische, Anatomie und Physiologie, und fuer Klinische Medizin. Vol. 320, Pg. 93, 1951.
hamster	LD50	intraperitoneal	7300ug/kg (7.3mg/kg)		Medicina Experimentalis. Vol. 6, Pg. 101, 1962.
human	LDLo	intravenous	129ug/kg (0.129mg/kg)	VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION VASCULAR: SHOCK GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Human Toxicology. Vol. 2, Pg. 169, 1983.
human	LDLo	oral	86ug/kg (0.086mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: OTHER CHANGES	"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 184, 1969.
human	TDLo	parenteral	710ug/kg (0.71mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION GASTROINTESTINAL: NAUSEA OR VOMITING	Archives of Internal Medicine. Vol. 137, Pg. 394, 1977.
man	LDLo	intravenous	143ug/kg/5D-I (0.143mg/kg)	BLOOD: APLASTIC ANEMIA MUSCULOSKELETAL: OTHER CHANGES	New England Journal of Medicine. Vol. 309, Pg. 310, 1983.
man	LDLo	oral	11mg/kg (11mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Canadian Medical Association Journal. Vol. 138, Pg. 335, 1988.
man	TDLo	oral	400ug/kg (0.4mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"	Critical Care Medicine. Vol. 7, Pg. 278, 1979.
man	TDLo	oral	12514ug/kg/2Y (12.514mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS	New England Journal of Medicine. Vol. 316, Pg. 1562, 1987.
mouse	LD50	intramuscular	1197ug/kg (1.197mg/kg)		Journal of Medicinal Chemistry. Vol. 24, Pg. 257, 1981.
mouse	LD50	intraperitoneal	1600ug/kg (1.6mg/kg)		Journal of Medicinal Chemistry. Vol. 28, Pg. 1204, 1985.
mouse	LD50	intravenous	1700ug/kg (1.7mg/kg)		Drugs in Japan Vol. 6, Pg. 280, 1982.
mouse	LD50	oral	5886ug/kg (5.886mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse	LD50	subcutaneous	1200ug/kg (1.2mg/kg)		Drugs in Japan Vol. 6, Pg. 280, 1982.
pigeon	LDLo	unreported	30mg/kg (30mg/kg)		Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 27, Pg. 119, 1890.
quail	LD50	oral	42mg/kg (42mg/kg)		Journal of Reproduction and Fertility. Vol. 48, Pg. 371, 1976.
rabbit	LDLo	intravenous	3mg/kg (3mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 67, Pg. 768, 1909.
rabbit	LDLo	oral	50mg/kg (50mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 67, Pg. 768, 1909.
rabbit	LDLo	subcutaneous	5mg/kg (5mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 67, Pg. 768, 1909.
rat	LD50	intravenous	1600ug/kg (1.6mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: FOOD INTAKE (ANIMAL) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Toxicology and Applied Pharmacology. Vol. 13, Pg. 50, 1968.
rat	LDLo	intracrebral	1mg/kg (1mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: EXCITEMENT BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 109, Pg. 386, 1957.
rat	LDLo	intraperitoneal	1400ug/kg (1.4mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS MUSCULOSKELETAL: OTHER CHANGES GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Archives of Neurology Vol. 24, Pg. 72, 1971.
rat	LDLo	parenteral	1000ug/kg (1mg/kg)		Farmaco, Edizione Scientifica. Vol. 15, Pg. 533, 1960.
rat	LDLo	subcutaneous	4mg/kg (4mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 84, Pg. 257, 1950.
rat	LDLo	unreported	1mg/kg (1mg/kg)		"Principles of Insect Chemosterilization," Labrecque, G.C., and C.N. Smith, eds., New York, Appleton-Century-Crofts, 1968Vol. -, Pg. 315, 1968.
women	LDLo	intravenous	360ug/kg/6D (0.36mg/kg)	KIDNEY, URETER, AND BLADDER: OTHER CHANGES BLOOD: HEMORRHAGE	Nouvelle Presse Medicale. Vol. 9, Pg. 1587, 1980.
women	LDLo	oral	600ug/kg (0.6mg/kg)	CARDIAC: OTHER CHANGES BLOOD: APLASTIC ANEMIA	American Journal of Emergency Medicine. Vol. 16, Pg. 603, 1998.
women	LDLo	oral	3mg/kg (3mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Japanese Journal of Toxicology. Vol. 12, Pg. 337, 1999.
women	LDLo	oral	8360ug/kg (8.36mg/kg)	CARDIAC: OTHER CHANGES KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Journal of Analytical Toxicology. Vol. 4, Pg. 153, 1980.
women	TDLo	oral	320ug/kg (0.32mg/kg)	PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	Lancet. Vol. 2, Pg. 1271, 1987.
women	TDLo	oral	510ug/kg (0.51mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: APLASTIC ANEMIA	Human & Experimental Toxicology. Vol. 16, Pg. 229, 1997.
women	TDLo	oral	960ug/kg (0.96mg/kg)	CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP	New England Journal of Medicine. Vol. 322, Pg. 642, 1995.
women	TDLo	oral	1mg/kg (1mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP BLOOD: LEUKOPENIA	Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 71, 1995.
women	TDLo	oral	4368ug/kg/26W (4.368mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Neurology. Vol. 41, Pg. 943, 1991.

Colchicine Consensus Reports

EPA Extremely Hazardous Substances List. EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Colchicine Safety Profile

A human poison by ingestion and intravenous routes. Poison experimentally by most routes. Human systemic effects: aplastic anemia, blood pressure depression, body temperature decrease, changes in kidney tubules, dyspnea, flaccid paralysis without anesthesia, gastrointestinal effects, kidney damage and hemorrhaging, muscle contraction or spasticity, muscle weakness, nausea or vomiting, respiratory stimulation, and somnolence. An experimental teratogen. Experimental reproductive effects. A severe eye irritant. Human mutation data reported. Inhibits the formation of microtubules and thus impairs cell division. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes: Very T+, Toxic T
Risk Statements: 26/28
R26/28:Very toxic by inhalation and if swallowed.
Safety Statements: 13-45
S13:Keep away from food, drink and animal foodstuffs.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 1544 6.1/PG 1
WGK Germany: 3
RTECS: GH0700000
HazardClass: 6.1
PackingGroup: I

Colchicine Specification

Colchicine (CAS NO.64-86-8), its Synonyms are 7-alpha-H-Colchicine ; 7alphaH-Colchicine ; AI3-31149 ; Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)- ; Benzo(a)heptalen-9(5H)-one, 7-acetamido-6,7-dihydro-1,2,3,10-tetramethoxy- ; Acetamide, N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)- ; Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)- . It is odorless or nearly odorless pale yellow needles or powder that darkens on exposure to light.

Product Name

Colchicine

Synthetic route

Colchicine Chemical Properties

Colchicine Uses

Colchicine Toxicity Data With Reference

Colchicine Consensus Reports

Colchicine Safety Profile

Colchicine Specification

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