(1R,2S,4aR,13bS,14aS)-methyl-2-hydroxy-1,2,4a,5,7,8,13,13b,14,14a-decahydroindolo[2',3':3,4]pyrido-[1,2-b]isoquinoline-1-carboxylate
Yohimbine
Conditions | Yield |
---|---|
With 10% Pd/C; hydrogen In ethyl acetate for 14h; | 100% |
With palladium 10% on activated carbon; hydrogen In ethyl acetate under 760.051 Torr; for 15h; | 100% |
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran at -78℃; for 0.5h; | 86% |
With sodium tetrahydroborate In isopropyl alcohol Product distribution; Reduction; |
Yohimbine
Conditions | Yield |
---|---|
With acetic acid at 160℃; for 0.0166667h; Reagent/catalyst; Temperature; Microwave irradiation; stereospecific reaction; | 74% |
Yohimbine
Conditions | Yield |
---|---|
With acetic acid at 160℃; for 0.0833333h; Microwave irradiation; stereospecific reaction; | 62% |
Yohimbine
Conditions | Yield |
---|---|
With acetic acid at 160℃; for 0.0166667h; Microwave irradiation; stereospecific reaction; | 59% |
4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester
Yohimbine
Conditions | Yield |
---|---|
With acetic acid at 160℃; for 0.0166667h; Time; Microwave irradiation; stereospecific reaction; | 50% |
Yohimbine
Conditions | Yield |
---|---|
With acetic acid at 160℃; for 0.0166667h; Microwave irradiation; stereospecific reaction; | 32% |
Yohimbine
Conditions | Yield |
---|---|
With acetic acid at 160℃; for 0.0833333h; Microwave irradiation; stereospecific reaction; | 17% |
Yohimbine
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate |
Yohimbine
Conditions | Yield |
---|---|
With acetic acid; zinc |
Conditions | Yield |
---|---|
With hydrogenchloride; methanol |
Conditions | Yield |
---|---|
With potassium hydroxide Behandeln des Reaktionsprodukts mit methanol.HCl; |
3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester
Yohimbine
Conditions | Yield |
---|---|
With N-Ac-Leu |
(+)-3,14-didehydroyohimbine
dibenzoyl peroxide
A
14α-benzoyloxypseudoyohimbine
B
14β-benzoyloxyyohimbine
C
Yohimbine
Conditions | Yield |
---|---|
With sodium tetrahydroborate Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel dichloride In methanol at 10 - 15℃; | A 47 mg B 25 mg |
(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
A
(+)-3,14-didehydroyohimbine
B
17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester
C
17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester
D
Yohimbine
Conditions | Yield |
---|---|
With sodium methylate In methanol for 0.666667h; Heating; Further byproducts given. Title compound not separated from byproducts; | A 16 % Spectr. B 27 % Spectr. C 22 % Spectr. D 18 % Spectr. |
(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
B
(+)-3,14-didehydroyohimbine
C
17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester
D
17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester
E
Yohimbine
Conditions | Yield |
---|---|
With sodium methylate In methanol for 0.666667h; Product distribution; Equilibrium constant; Mechanism; Heating; solvolysis by KOH, MeOH, NaOMe; | A 17 % Spectr. B 16 % Spectr. C 27 % Spectr. D 22 % Spectr. E 18 % Spectr. |
Yohimbine
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid Behandeln des Reaktionsprodukts mit Diazomethan in Methanol und Aether; |
water
hydrogen bromide
acetic acid
pseudoyohimbine
Yohimbine
Conditions | Yield |
---|---|
Behandeln des Reaktionsprodukts mit Diazomethan in Methanol und Aether; |
Conditions | Yield |
---|---|
Behandeln des Reaktionsprodukts mit methanol.HCl; |
Conditions | Yield |
---|---|
With acetic acid for 96h; Isomerization; epimerisation; Heating; | |
With acetic acid for 48h; Heating; |
Conditions | Yield |
---|---|
In methanol | 1.8 mg |
secologanin
Yohimbine
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: pyridine / 12 h 2: TFA / tetrahydrofuran / 1 h / Heating 3: NaOMe / methanol / 12 h 4: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0 5: 85 percent / NaCNBH3 / methanol / 48 h 6: 75 percent / aq. HCl / acetone / 2 h / Heating 7: 100 percent / H2 / Pd/C / methanol 8: DMSO; Ac2O / 16 h 9: NaBH4 / propan-2-ol / 20 h 10: glacial acetic acid / 48 h / Heating View Scheme | |
Multi-step reaction with 9 steps 1.1: pyridine / 12 h 2.1: TFA / 1 h / 13 °C / Heating 3.1: NaOMe / methanol / 12 h 4.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 5.1: methanol 5.2: 85 percent / NaCNBH3 / methanol 6.1: 75 percent / HCl (10 percent) / 2 h / Heating 7.1: hydrogen / PtO2 / ethanol / 24 h 8.1: DMSO; Ac2O 9.1: NaBH4 / propan-2-ol View Scheme | |
Multi-step reaction with 10 steps 1.1: pyridine / 12 h 2.1: TFA / 1 h / 13 °C / Heating 3.1: NaOMe / methanol / 12 h 4.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 5.1: methanol 5.2: 85 percent / NaCNBH3 / methanol 6.1: 75 percent / HCl (10 percent) / 2 h / Heating 7.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 8.1: DMSO; Ac2O / 16 h 9.1: NaBH4 / propan-2-ol / 20 h 10.1: AcOH / 96 h / Heating View Scheme | |
Multi-step reaction with 10 steps 1.1: pyridine / 12 h 2.1: TFA / 1 h / 13 °C / Heating 3.1: NaOMe / methanol / 12 h 4.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 5.1: methanol 5.2: 85 percent / NaCNBH3 / methanol 6.1: 75 percent / HCl (10 percent) / 2 h / Heating 7.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 8.1: AcOH / 96 h / Heating 9.1: DMSO; Ac2O 10.1: NaBH4 / propan-2-ol View Scheme |
O,O,O,O-tetraacetylsecologaninn
Yohimbine
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: TFA / tetrahydrofuran / 1 h / Heating 2: NaOMe / methanol / 12 h 3: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0 4: 85 percent / NaCNBH3 / methanol / 48 h 5: 75 percent / aq. HCl / acetone / 2 h / Heating 6: 100 percent / H2 / Pd/C / methanol 7: DMSO; Ac2O / 16 h 8: NaBH4 / propan-2-ol / 20 h 9: glacial acetic acid / 48 h / Heating View Scheme | |
Multi-step reaction with 8 steps 1.1: TFA / 1 h / 13 °C / Heating 2.1: NaOMe / methanol / 12 h 3.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 4.1: methanol 4.2: 85 percent / NaCNBH3 / methanol 5.1: 75 percent / HCl (10 percent) / 2 h / Heating 6.1: hydrogen / PtO2 / ethanol / 24 h 7.1: DMSO; Ac2O 8.1: NaBH4 / propan-2-ol View Scheme | |
Multi-step reaction with 9 steps 1.1: TFA / 1 h / 13 °C / Heating 2.1: NaOMe / methanol / 12 h 3.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 4.1: methanol 4.2: 85 percent / NaCNBH3 / methanol 5.1: 75 percent / HCl (10 percent) / 2 h / Heating 6.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 7.1: DMSO; Ac2O / 16 h 8.1: NaBH4 / propan-2-ol / 20 h 9.1: AcOH / 96 h / Heating View Scheme | |
Multi-step reaction with 9 steps 1.1: TFA / 1 h / 13 °C / Heating 2.1: NaOMe / methanol / 12 h 3.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 4.1: methanol 4.2: 85 percent / NaCNBH3 / methanol 5.1: 75 percent / HCl (10 percent) / 2 h / Heating 6.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 7.1: AcOH / 96 h / Heating 8.1: DMSO; Ac2O 9.1: NaBH4 / propan-2-ol View Scheme |
Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate
Yohimbine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0 2: 85 percent / NaCNBH3 / methanol / 48 h 3: 75 percent / aq. HCl / acetone / 2 h / Heating 4: 100 percent / H2 / Pd/C / methanol 5: DMSO; Ac2O / 16 h 6: NaBH4 / propan-2-ol / 20 h 7: glacial acetic acid / 48 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 2.1: methanol 2.2: 85 percent / NaCNBH3 / methanol 3.1: 75 percent / HCl (10 percent) / 2 h / Heating 4.1: hydrogen / PtO2 / ethanol / 24 h 5.1: DMSO; Ac2O 6.1: NaBH4 / propan-2-ol View Scheme | |
Multi-step reaction with 7 steps 1.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 2.1: methanol 2.2: 85 percent / NaCNBH3 / methanol 3.1: 75 percent / HCl (10 percent) / 2 h / Heating 4.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 5.1: DMSO; Ac2O / 16 h 6.1: NaBH4 / propan-2-ol / 20 h 7.1: AcOH / 96 h / Heating View Scheme | |
Multi-step reaction with 7 steps 1.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 2.1: methanol 2.2: 85 percent / NaCNBH3 / methanol 3.1: 75 percent / HCl (10 percent) / 2 h / Heating 4.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 5.1: AcOH / 96 h / Heating 6.1: DMSO; Ac2O 7.1: NaBH4 / propan-2-ol View Scheme |
Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate
Yohimbine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: NaOMe / methanol / 12 h 2: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0 3: 85 percent / NaCNBH3 / methanol / 48 h 4: 75 percent / aq. HCl / acetone / 2 h / Heating 5: 100 percent / H2 / Pd/C / methanol 6: DMSO; Ac2O / 16 h 7: NaBH4 / propan-2-ol / 20 h 8: glacial acetic acid / 48 h / Heating View Scheme | |
Multi-step reaction with 7 steps 1.1: NaOMe / methanol / 12 h 2.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 3.1: methanol 3.2: 85 percent / NaCNBH3 / methanol 4.1: 75 percent / HCl (10 percent) / 2 h / Heating 5.1: hydrogen / PtO2 / ethanol / 24 h 6.1: DMSO; Ac2O 7.1: NaBH4 / propan-2-ol View Scheme | |
Multi-step reaction with 8 steps 1.1: NaOMe / methanol / 12 h 2.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 3.1: methanol 3.2: 85 percent / NaCNBH3 / methanol 4.1: 75 percent / HCl (10 percent) / 2 h / Heating 5.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 6.1: DMSO; Ac2O / 16 h 7.1: NaBH4 / propan-2-ol / 20 h 8.1: AcOH / 96 h / Heating View Scheme | |
Multi-step reaction with 8 steps 1.1: NaOMe / methanol / 12 h 2.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0 3.1: methanol 3.2: 85 percent / NaCNBH3 / methanol 4.1: 75 percent / HCl (10 percent) / 2 h / Heating 5.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 6.1: AcOH / 96 h / Heating 7.1: DMSO; Ac2O 8.1: NaBH4 / propan-2-ol View Scheme |
17-oxo-yohimbane-16-carboxylic acid methyl ester
Yohimbine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaBH4 / propan-2-ol / 20 h 2: glacial acetic acid / 48 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: NaBH4 / propan-2-ol / 20 h 2: AcOH / 96 h / Heating View Scheme |
(1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-3-formyl-6-hydroxy-cyclohex-3-enecarboxylic acid methyl ester
Yohimbine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 85 percent / NaCNBH3 / methanol / 48 h 2: 75 percent / aq. HCl / acetone / 2 h / Heating 3: 100 percent / H2 / Pd/C / methanol 4: DMSO; Ac2O / 16 h 5: NaBH4 / propan-2-ol / 20 h 6: glacial acetic acid / 48 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1.1: methanol 1.2: 85 percent / NaCNBH3 / methanol 2.1: 75 percent / HCl (10 percent) / 2 h / Heating 3.1: hydrogen / PtO2 / ethanol / 24 h 4.1: DMSO; Ac2O 5.1: NaBH4 / propan-2-ol View Scheme | |
Multi-step reaction with 6 steps 1.1: methanol 1.2: 85 percent / NaCNBH3 / methanol 2.1: 75 percent / HCl (10 percent) / 2 h / Heating 3.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 4.1: DMSO; Ac2O / 16 h 5.1: NaBH4 / propan-2-ol / 20 h 6.1: AcOH / 96 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1.1: methanol 1.2: 85 percent / NaCNBH3 / methanol 2.1: 75 percent / HCl (10 percent) / 2 h / Heating 3.1: 100 percent / hydrogen / Pd/C / methanol / 12 h 4.1: AcOH / 96 h / Heating 5.1: DMSO; Ac2O 6.1: NaBH4 / propan-2-ol View Scheme |
(-)-3-iso-19,20-dehydro-β-yohimbine
Yohimbine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / H2 / Pd/C / methanol 2: DMSO; Ac2O / 16 h 3: NaBH4 / propan-2-ol / 20 h 4: glacial acetic acid / 48 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: hydrogen / PtO2 / ethanol / 24 h 2: DMSO; Ac2O 3: NaBH4 / propan-2-ol View Scheme | |
Multi-step reaction with 4 steps 1: 100 percent / hydrogen / Pd/C / methanol / 12 h 2: DMSO; Ac2O / 16 h 3: NaBH4 / propan-2-ol / 20 h 4: AcOH / 96 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 100 percent / hydrogen / Pd/C / methanol / 12 h 2: AcOH / 96 h / Heating 3: DMSO; Ac2O 4: NaBH4 / propan-2-ol View Scheme |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 94% |
Yohimbine
Conditions | Yield |
---|---|
With sodium amide for 5 - 6h; Heating / reflux; | 90% |
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride 2: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide View Scheme |
Yohimbine
Conditions | Yield |
---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 22h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With sodium cyanoborohydride In trifluoroacetic acid | A 89% B 9% |
With sodium cyanoborohydride In trifluoroacetic acid at 20℃; for 3h; | A 79% B 18% |
With sodium tetrahydroborate; trifluoroacetic acid | A 68% B 1% |
Conditions | Yield |
---|---|
With mercury(II) diacetate at 60℃; | 85% |
Conditions | Yield |
---|---|
With ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 40℃; for 3h; | 83% |
With ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 40℃; for 3h; | 83% |
Conditions | Yield |
---|---|
With ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20 - 40℃; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With phosphoric acid; dicyclohexyl-carbodiimide In dimethyl sulfoxide | 81% |
Conditions | Yield |
---|---|
Stage #1: allyl methyl carbonate With tris(dibenzylideneacetone)dipalladium (0); trifuran-2-yl-phosphane In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: Yohimbine In dichloromethane at 20℃; Inert atmosphere; diastereoselective reaction; | 79% |
dicobalt octacarbonyl
Yohimbine
Conditions | Yield |
---|---|
Stage #1: dicobalt octacarbonyl; 6CO*2Co*C12H21BrF2Si In dichloromethane; toluene at 20℃; for 3h; Inert atmosphere; Stage #2: Yohimbine With silver trifluoromethanesulfonate; triethylamine In dichloromethane; toluene for 0.5h; Inert atmosphere; chemoselective reaction; | 74% |
Yohimbine
Conditions | Yield |
---|---|
With dihydrogen peroxide In methanol at 60℃; for 6h; | 70% |
Conditions | Yield |
---|---|
In dichloromethane for 0.25h; Ambient temperature; | 67% |
Yohimbine
A
(1R,2S,4aR,8aS,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
B
(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With tert-butylhypochlorite; triethylamine In dichloromethane | A 67% B 28% |
With tert-butylhypochlorite In tetrachloromethane; dichloromethane at -17℃; for 0.5h; | A 55% B 32% |
Yohimbine
Conditions | Yield |
---|---|
With mercury(II) diacetate; edetate disodium In acetic acid for 1.5h; Heating; | 66% |
With mercury(II) diacetate; edetate disodium In acetic acid for 1.5h; Heating; Yield given; |
bromocyane
Yohimbine
A
4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester
B
4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran; dichloromethane; water at 20℃; for 23h; Inert atmosphere; | A n/a B 63% |
With water In tetrahydrofuran; dichloromethane at 20℃; for 23h; Inert atmosphere; Overall yield = 63 %; Overall yield = 208 mg; | A n/a B n/a |
Conditions | Yield |
---|---|
In dichloromethane; N,N-dimethyl-formamide at 100℃; for 0.000763889h; Microwave irradiation; Sealed tube; | 56% |
In dichloromethane; N,N-dimethyl-formamide at 100℃; for 0.0458333h; Microwave irradiation; Inert atmosphere; | 56% |
Conditions | Yield |
---|---|
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere; | 55% |
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere; | 36% |
Conditions | Yield |
---|---|
With silver(l) oxide at 20℃; for 8h; stereoselective reaction; | A 55% B 20% |
bromocyane
ethanol
Yohimbine
B
4-cyano-3-ethoxy-17-hydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere; | A n/a B 47% |
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere; Overall yield = 47 %; Overall yield = 171 mg; | A n/a B n/a |
Conditions | Yield |
---|---|
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere; | A 39% B 9% |
Yohimbine
Conditions | Yield |
---|---|
With dmap In acetonitrile at 20℃; | 37% |
Conditions | Yield |
---|---|
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere; | A 37% B 8% |
In dichloromethane; chloroform for 4h; Reflux; Inert atmosphere; | A 37% B 8% |
Conditions | Yield |
---|---|
With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 40℃; for 3h; | 35% |
Conditions | Yield |
---|---|
With formic acid; silver(l) oxide In acetonitrile at 40℃; for 12h; stereoselective reaction; | 35% |
The CAS registry number of Yohimbine is 146-48-5. Its EINECS registry number is 205-672-0. The systematic name is methyl (16α,17α)-17-hydroxyyohimban-16-carboxylate. In addition, the molecular formula is C21H26N2O3 and the molecular weight is 354.44. What's more, it is an alkaloid with stimulant and aphrodisiac effects found naturally in Pausinystalia yohimbe and belongs to the classes of Adrenoceptor and API.
Physical properties about this chemical are: (1)ACD/LogP: 2.20; (2)ACD/LogD (pH 5.5): -0.56; (3)ACD/LogD (pH 7.4): 1.05; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1.95; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 26.39; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 43.7 Å2; (12)Index of Refraction: 1.66; (13)Molar Refractivity: 99.46 cm3; (14)Molar Volume: 269.1 cm3; (15)Polarizability: 39.42 ×10-24cm3; (16)Surface Tension: 63.3 dyne/cm; (17)Density: 1.31 g/cm3; (18)Flash Point: 282.2 °C; (19)Enthalpy of Vaporization: 86.43 kJ/mol; (20)Boiling Point: 543 °C at 760 mmHg; (21)Vapour Pressure: 1.27E-12 mmHg at 25°C.
Preparation of Yohimbine: it can be prepared by yohimbinone. The other product is (+/-)-b-yohimbine. This reaction will need reagent sodium borohydride and solvent methanol. The reaction time is 20 minutes at reaction temperature of 0 °C. The yield is about 52.9%.
Uses of Yohimbine: it has been used to facilitate recall of traumatic memories in the treatment of posttraumatic stress disorder. And it can be used in arteriosclerosis and angina pectoris, and has been used as a local anesthetic and mydriatic and for its purported aphrodisiac properties. In addition, it can be used as both an over-the-counter dietary supplement in herbal extract form and prescription medicine in pure form for the treatment of sexual dysfunction.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation, in contact with skin and if swallowed. And it has danger of very serious irreversible effects. During using it, wear suitable protective clothing, gloves and eye/face protection. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). In addition, you should take off immediately all contaminated clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)[C@@H]5[C@H]4C[C@H]3c2nc1ccccc1c2CCN3C[C@@H]4CC[C@@H]5O
(2)InChI: InChI=1/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
(3)InChIKey: BLGXFZZNTVWLAY-SCYLSFHTBA
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | oral | 643ug/kg/3W-I (0.643mg/kg) | BEHAVIORAL: EXCITEMENT VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Life Sciences. Vol. 30, Pg. 2033, 1982. |
man | TDLo | oral | 694ug/kg/3D-I (0.694mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION | British Journal of Psychiatry. Vol. 169, Pg. 384, 1996. |
mouse | LD50 | intraperitoneal | 16mg/kg (16mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955. | |
mouse | LD50 | oral | 43mg/kg (43mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955. | |
mouse | LD50 | subcutaneous | 37mg/kg (37mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955. | |
rabbit | LDLo | intravenous | 11mg/kg (11mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1418, 1935. | |
rabbit | LDLo | subcutaneous | 50mg/kg (50mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1418, 1935. | |
women | TDLo | oral | 5gm/kg (5000mg/kg) | PERIPHERAL NERVE AND SENSATION: PARESTHESIS BEHAVIORAL: ATAXIA CARDIAC: CHANGE IN RATE | Annals of Emergency Medicine. Vol. 14, Pg. 1002, 1985. |
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View