Yohimbine supplier | CasNO.146-48-5

Name
17alpha-Hydroxy-yohimban-16alpha-carboxylic acid methyl ester
EINECS 205-672-0
CAS No. 146-48-5
Article Data42
CAS DataBase
Density 1.31 g/cm³
Solubility
Melting Point 231-233 °C(lit.)
Formula C₂₁H₂₆N₂O₃
Boiling Point 543 °C at 760 mmHg
Molecular Weight 354.449
Flash Point 282.2 °C
Transport Information
Appearance
Safety 27-36/37/39-45
Risk Codes 23/24/25-39
Molecular Structure
Hazard Symbols T
Synonyms Yohimban-16a-carboxylic acid, 17a-hydroxy-, methyl ester (8CI);Yohimbol-16a-carboxylic acid, methyl ester(6CI);(+)-Yohimbine;Aphrodine;Aphrosol;Corynine;Quebrachin;Quebrachine;Yohimbicacid methyl ester;Yohimbin;Yohimbine;trans-Quinolizidine yohimbine;
PSA 65.56000
LogP 2.58500

Synthetic route

: 1011533-78-0
(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

: 146-48-5
Yohimbine

Conditions

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%

: 2671-57-0
(+)-yohimbinone

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With L-Selectride In tetrahydrofuran at -78℃; for 0.5h;	86%
With sodium tetrahydroborate In isopropyl alcohol Product distribution; Reduction;

: C23H29N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0166667h; Reagent/catalyst; Temperature; Microwave irradiation; stereospecific reaction;	74%

: C25H33N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0833333h; Microwave irradiation; stereospecific reaction;	62%

: C28H31N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0166667h; Microwave irradiation; stereospecific reaction;	59%

: 23943-82-0, 25181-38-8
4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0166667h; Time; Microwave irradiation; stereospecific reaction;	50%

: C28H31N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0166667h; Microwave irradiation; stereospecific reaction;	32%

: C25H33N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0833333h; Microwave irradiation; stereospecific reaction;	17%

: 17α-hydroxy-16α-methoxycarbonyl-yohimba-3,5-dienium; perchlorate

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate

: 17α-hydroxy-16α-methoxycarbonyl-yohimb-3-enium; perchlorate

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid; zinc

: 522-87-2
yohimbinic acid

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With hydrogenchloride; methanol

: 483-10-3
corynanthine

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With potassium hydroxide Behandeln des Reaktionsprodukts mit methanol.HCl;

: 84-37-7, 131-03-3, 146-48-5, 483-09-0, 483-10-3, 522-92-9, 522-94-1, 549-82-6, 549-84-8, 2516-78-1, 6835-85-4, 24252-70-8, 25920-66-5, 40085-29-8, 40085-30-1, 40085-32-3, 40088-19-5, 40088-20-8, 40088-25-3, 41787-60-4, 41904-78-3, 59904-75-5, 59952-52-2, 59952-53-3, 59952-56-6, 83540-86-7, 83540-88-9, 103834-06-6, 103834-07-7
3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With N-Ac-Leu

: 90362-85-9
(+)-3,14-didehydroyohimbine

: 94-36-0
dibenzoyl peroxide

A: 90362-87-1, 90410-87-0
14α-benzoyloxypseudoyohimbine

B: 90362-87-1, 90410-87-0
14β-benzoyloxyyohimbine

C: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With sodium tetrahydroborate Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 51598-49-3
(-)-Δ15,16-didehydroyohimbinone

A: 549-84-8
β-yohimbine

B: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol at 10 - 15℃;	A 47 mg B 25 mg

: 94992-42-4
(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: 90362-85-9
(+)-3,14-didehydroyohimbine

B: 71748-23-7
17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester

C: 36193-50-7
17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester

D: 146-48-5
Yohimbine

Conditions

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.

...Expand

: 94992-42-4
(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: 3,4,5,6-tetradehydroyohimbine

B: 90362-85-9
(+)-3,14-didehydroyohimbine

C: 71748-23-7
17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester

D: 36193-50-7
17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester

E: 146-48-5
Yohimbine

Conditions

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.

...Expand

(+)-pseudoyohimbin: (+)-pseudoyohimbin

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid Behandeln des Reaktionsprodukts mit Diazomethan in Methanol und Aether;

: 7732-18-5
water

: 10035-10-6, 12258-64-9
hydrogen bromide

: 64-19-7
acetic acid

: 84-37-7
pseudoyohimbine

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
Behandeln des Reaktionsprodukts mit Diazomethan in Methanol und Aether;

...Expand

: 64-17-5
ethanol

: 483-10-3
corynanthine

KOH: KOH

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
Behandeln des Reaktionsprodukts mit methanol.HCl;

...Expand

: 84-37-7
pseudoyohimbine

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid for 96h; Isomerization; epimerisation; Heating;
With acetic acid for 48h; Heating;

: 18107-18-1
diazomethyl-trimethyl-silane

: 522-87-2
yohimbinic acid

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
In methanol	1.8 mg

: 19351-63-4
secologanin

: 146-48-5
Yohimbine

Conditions

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

: 27856-66-2
O,O,O,O-tetraacetylsecologaninn

: 146-48-5
Yohimbine

Conditions

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

: 79409-45-3
Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate

: 146-48-5
Yohimbine

Conditions

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

: 79409-46-4
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

: 146-48-5
Yohimbine

Conditions

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

: 114030-03-4
17-oxo-yohimbane-16-carboxylic acid methyl ester

: 146-48-5
Yohimbine

Conditions

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

: 120132-02-7
(1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-3-formyl-6-hydroxy-cyclohex-3-enecarboxylic acid methyl ester

: 146-48-5
Yohimbine

Conditions

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

: 295790-93-1
(-)-3-iso-19,20-dehydro-β-yohimbine

: 146-48-5
Yohimbine

Conditions

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

: 146-48-5
Yohimbine

: 6784-29-8
Yohimbyl alcohol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride	94%

: 146-48-5
Yohimbine

: yohimban-17-amide

Conditions

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

: 146-48-5
Yohimbine

: C21H23(2)H3N2O3

Conditions

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 22h; Inert atmosphere;	90%

: 146-48-5
Yohimbine

A: 142696-96-6
2α,7α-dihydroyohimbine

B: 364777-85-5
2β,7β-dihydroyohimbine

Conditions

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%

: 64-19-7
acetic acid

: 146-48-5
Yohimbine

: Acetate(1R,2S,4aR,14aS)-2-hydroxy-1-methoxycarbonyl-2,3,4,4a,5,7,8,13,14,14a-decahydro-1H-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-6-ylium;

Conditions

Conditions	Yield
With mercury(II) diacetate at 60℃;	85%

: 107-21-1
ethylene glycol

: 146-48-5
Yohimbine

: C23H30N2O5

Conditions

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%

: 107-21-1
ethylene glycol

: 146-48-5
Yohimbine

: C23H30N2O5

Conditions

Conditions	Yield
With ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20 - 40℃; Inert atmosphere;	83%

: 146-48-5
Yohimbine

: 2671-57-0
(+)-yohimbinone

Conditions

Conditions	Yield
With phosphoric acid; dicyclohexyl-carbodiimide In dimethyl sulfoxide	81%

: 35466-83-2
allyl methyl carbonate

: 146-48-5
Yohimbine

: 1029578-58-2
(7R)-allylyohimbine

Conditions

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%

: 15226-74-1, 61091-28-9, 61117-58-6
dicobalt octacarbonyl

: 6CO*2Co*C12H21BrF2Si

: 146-48-5
Yohimbine

: 6CO*2Co*C33H46F2N2O3Si

Conditions

Conditions	Yield
Stage #1: dicobalt octacarbonyl; 6CO2CoC12H21BrF2Si 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%

...Expand

: 146-48-5
Yohimbine

: (1R,2S,4aR,13bS,14aS)-2-Hydroxy-6-oxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

Conditions

Conditions	Yield
With dihydrogen peroxide In methanol at 60℃; for 6h;	70%

: 546-67-8
lead(IV) tetraacetate

: 146-48-5
Yohimbine

: 94992-43-5
(+)-7α-acetoxy-7H-yohimbine

Conditions

Conditions	Yield
In dichloromethane for 0.25h; Ambient temperature;	67%

: 146-48-5
Yohimbine

A: 94992-41-3
(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: 94992-42-4
(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

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%

: 146-48-5
Yohimbine

: 3,4-Didehydroyohimbin

Conditions

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;

: 506-68-3
bromocyane

: 146-48-5
Yohimbine

A: 23943-82-0, 25181-38-8
4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

B: 23943-82-0, 25181-38-8
4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

Conditions

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

...Expand

: 506-68-3
bromocyane

: 146-48-5
Yohimbine

: C22H26BrN3O3

Conditions

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%

: 67-56-1
methanol

: 506-68-3
bromocyane

: 146-48-5
Yohimbine

: C23H29N3O4

Conditions

Conditions	Yield
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere;	55%
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere;	36%

...Expand

: 64-18-6
formic acid

: 303-38-8
2,3-Dihydroxybenzoic acid

: 146-48-5
Yohimbine

A: C28H30N2O7

B: C29H30N2O8

Conditions

Conditions	Yield
With silver(l) oxide at 20℃; for 8h; stereoselective reaction;	A 55% B 20%

...Expand

: 506-68-3
bromocyane

: 64-17-5
ethanol

: 146-48-5
Yohimbine

A: C24H31N3O4

B: 23943-81-9, 23943-84-2, 23944-14-1, 38739-02-5
4-cyano-3-ethoxy-17-hydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

Conditions

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

...Expand

: 506-68-3
bromocyane

: 67-63-0
isopropyl alcohol

: 146-48-5
Yohimbine

A: C25H33N3O4

B: C25H33N3O4

Conditions

Conditions	Yield
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere;	A 39% B 9%

...Expand

: 3-cyanocarbonyl-3'-methoxycarbonyl-2,2'-binaphthalene

: 146-48-5
Yohimbine

: [2,2']binaphthalenyl-1,3'-dicarboxylic acid 1-(1-methoxycarbonyl-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-2-yl) ester 3'-methyl ester

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃;	37%

: 506-68-3
bromocyane

: 100-51-6
benzyl alcohol

: 146-48-5
Yohimbine

A: C29H33N3O4

B: C29H33N3O4

Conditions

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%

...Expand

: 107-21-1
ethylene glycol

: 146-48-5
Yohimbine

: 1016560-15-8
C23H30N2O5

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 40℃; for 3h;	35%

: 303-38-8
2,3-Dihydroxybenzoic acid

: 146-48-5
Yohimbine

: C28H30N2O7

Conditions

Conditions	Yield
With formic acid; silver(l) oxide In acetonitrile at 40℃; for 12h; stereoselective reaction;	35%

Yohimbine Standards and Recommendations

IDENTITY: Complies
CONTENT: 98.0% min
MOISTURE: 1.0% max
HEAVY METALS: 10ppm max

Yohimbine Specification

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%.

Yohimbine can be prepared by yohimbinone. The other product is (+/-)-b-yohimbine

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.

Product Name

17alpha-Hydroxy-yohimban-16alpha-carboxylic acid methyl ester

Synthetic route

Yohimbine Standards and Recommendations

Yohimbine Specification

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