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99300-78-4

Basic Information
CAS No.: 99300-78-4
Name: Venlafaxine hydrochloride
Molecular Structure:
Molecular Structure of 99300-78-4 (Venlafaxine hydrochloride)
Formula: C17H28ClNO2
Molecular Weight: 313.86
Synonyms: 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol;Cyclohexanol,1-[2-(dimethylamino)-1-(4- methoxyphenyl)ethyl]-,hydrochloride;Venlafaxina [INN-Spanish];venlafaxine HCl;Effexor XR;Elafax;Venlafaxine hydrochloride (JAN/USAN);Effexor (TN);Cyclohexanol, 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)-, hydrochloride;Venlafaxine Hydrochlorid;Venlafaxin HCL;Wy-45030;Effexor;Wy-45,030;Venlafaxinum [INN-Latin];(+-)-1-(alpha-((Dimethylamino)methyl)-p-methoxybenzyl)cyclohexanol hydrochloride;N,N-dimethyl-2-p-methoxy- phenyl-2-(1-hydroxycyclohexyl) ethylamine hyd- rochloride;
EINECS: 200-659-6
Density: 1.394 g/cm3
Melting Point: 207-209 °C
Boiling Point: 397.6 °C at 760 mmHg
Flash Point: 194.2 °C
Solubility:
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 32.70000
LogP: 3.83760
Synthetic route
93413-69-5

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; ethyl acetate at 68 - 73℃; pH=2.5;95%
With hydrogenchloride In ethyl acetate; isopropyl alcohol for 1h; Reflux;87%
With hydrogenchloride In isopropyl alcohol at 5 - 80℃; for 1.5 - 2h; Product distribution / selectivity;75%
50-00-0

formaldehyd

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With sodium hydroxide In methanol at 0 - 5℃; for 0.5h; pH=9 - 9.5;
Stage #2: formaldehyd With formic acid In water at 20 - 100℃; for 14 - 15h;
Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;
95%
50-00-0

formaldehyd

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hemisulfate

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; formic acid In dichloromethane; water pH=1; Reflux;94.2%
Stage #1: formaldehyd; 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hemisulfate With formic acid In water Reflux;
Stage #2: With hydrogenchloride In water
93.8%

[RS]-1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol acetic acid

50-00-0

formaldehyd

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Stage #1: [RS]-1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol acetic acid; formaldehyd With formic acid In water at 98℃; for 20h;
Stage #2: With hydrogenchloride In isopropyl alcohol at 10 - 60℃; for 2 - 2.5h; pH=1 - 1.5;
84%
Stage #1: [RS]-1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol acetic acid; formaldehyd With formic acid In water at 90 - 98℃; for 19h;
Stage #2: With sodium hydroxide In water at 5℃;
Stage #3: With hydrogenchloride In i-Amyl alcohol pH=~ 2;
50-00-0

formaldehyd

64-18-6

formic acid

93413-76-4

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Stage #1: With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 5℃; for 1 - 1.5h;
Stage #2: 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol In tetrahydrofuran at 0 - 40℃; for 5 - 6.5h;
Stage #3: formaldehyd; formic acid With hydrogenchloride Product distribution / selectivity; more than 3 stages;
78.25%

1-[(4-methoxyphenyl)(dimethylamino)carbonylmethyl]cyclohexanol

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-[(4-methoxyphenyl)(dimethylamino)carbonylmethyl]cyclohexanol With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 0 - 2℃; for 3 - 4h;
Stage #2: With sodium hydroxide In water; toluene at 0 - 30℃; for 0.25 - 0.5h;
Stage #3: With hydrogenchloride In ethyl acetate; isopropyl alcohol at 25℃; for 2h;
In tetrahydrofuran at 0℃; for 1h;
50-00-0

formaldehyd

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Stage #1: formaldehyd; 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With formic acid In water at 97 - 99℃; for 16h;
Stage #2: With hydrogenchloride In isopropyl alcohol at 10℃; for 1 - 2h; pH=2.0;
130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With formic acid; hexamethylenetetramine In water at 20 - 102℃; for 0.25h;
Stage #2: With sodium hydroxide In water at 15 - 20℃; pH=10 - 11; Product distribution / selectivity;
50-00-0

formaldehyd

93413-77-5, 272788-06-4, 273720-73-3

N,N-didesmethylvenlafaxine

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Stage #1: formaldehyd; N,N-didesmethylvenlafaxine With formic acid In water at 95 - 100℃;
Stage #2: With sodium hydroxide In water pH=> 12;
Stage #3: With hydrogenchloride In water at 25 - 30℃;
Stage #1: formaldehyd; N,N-didesmethylvenlafaxine With formic acid In water
Stage #2: With hydrogenchloride In isopropyl alcohol

[RS]-1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol acetic acid

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: formic acid / water / 22 h / 100 °C / Large scale reaction
2: hydrogenchloride / water; isopropyl alcohol; toluene / 2 h / 0 - 5 °C / pH 3 - 4.5 / Large scale reaction
View Scheme
108-94-1

cyclohexanone

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium methylate / methanol / 2 h / 0 - 5 °C / Large scale reaction
1.2: 4 h / 0 - 5 °C / Large scale reaction
2.1: hydrogen / 3 h / 55 °C / 7500.75 - 9000.9 Torr / Large scale reaction
3.1: formic acid / water / 22 h / 100 °C / Large scale reaction
4.1: hydrogenchloride / water; isopropyl alcohol; toluene / 2 h / 0 - 5 °C / pH 3 - 4.5 / Large scale reaction
View Scheme
93413-76-4

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen / 3 h / 55 °C / 7500.75 - 9000.9 Torr / Large scale reaction
2: formic acid / water / 22 h / 100 °C / Large scale reaction
3: hydrogenchloride / water; isopropyl alcohol; toluene / 2 h / 0 - 5 °C / pH 3 - 4.5 / Large scale reaction
View Scheme
Multi-step reaction with 3 steps
1: hydrogen / ethyl acetate / 40 °C / 2250.23 - 3000.3 Torr
2: sulfuric acid / ethyl acetate / 2 h / 0 - 10 °C
3: formic acid; hydrogenchloride / water; dichloromethane / pH 1 / Reflux
View Scheme
104-47-2

p-methoxybenzylnitrile

99300-78-4

venlafaxine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium methylate / methanol / 2 h / 0 - 5 °C / Large scale reaction
1.2: 4 h / 0 - 5 °C / Large scale reaction
2.1: hydrogen / 3 h / 55 °C / 7500.75 - 9000.9 Torr / Large scale reaction
3.1: formic acid / water / 22 h / 100 °C / Large scale reaction
4.1: hydrogenchloride / water; isopropyl alcohol; toluene / 2 h / 0 - 5 °C / pH 3 - 4.5 / Large scale reaction
View Scheme
99300-78-4

venlafaxine hydrochloride

93413-69-5

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol

Conditions
ConditionsYield
With sodium hydroxide In water98.9%
With sodium hydroxide In water pH=12 - 13;
With sodium hydroxide In dichloromethane; water at 25 - 35℃; pH=12 - 13;
99300-78-4

venlafaxine hydrochloride

93413-62-8

O-desmethylvenlafaxine

Conditions
ConditionsYield
Stage #1: venlafaxine hydrochloride With sodium hydride; ethanethiol In N,N-dimethyl-formamide at 0 - 140℃; for 7h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 35℃; pH=2 - 3;
92%
Stage #1: venlafaxine hydrochloride With sodium hydride; ethanethiol In N,N-dimethyl-formamide at 0 - 140℃;
Stage #2: With hydrogenchloride; pyrographite In water; N,N-dimethyl-formamide at 35℃; for 0.5h; Industry scale;
Stage #3: With sodium hydroxide In water pH=8.5 - 9; Industry scale;
92%
Stage #1: venlafaxine hydrochloride With potassium tert-butylate; ethane-1,2-dithiol In decaethylene glycol at 25 - 135℃; for 24 - 28h;
Stage #2: With hydrogenchloride; water In decaethylene glycol at 25 - 30℃;
Stage #3: With ammonia In water pH=> 9.5; Product distribution / selectivity;
84%
99300-78-4

venlafaxine hydrochloride

300827-87-6

O-desvenlafaxine hydrochloride

Conditions
ConditionsYield
With methanesulfonic acid; L-methionine Large scale;88.5%
1947-00-8

6-(benzyloxycarbonylamino)hexanoic acid

99300-78-4

venlafaxine hydrochloride

1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexyl 6-(((benzyloxy)carbonyl)amino)hexanoate

Conditions
ConditionsYield
Stage #1: 6-(benzyloxycarbonylamino)hexanoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;
Stage #2: venlafaxine hydrochloride In dichloromethane at 45℃; for 6h;
77.8%
Stage #1: 6-(benzyloxycarbonylamino)hexanoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;
Stage #2: venlafaxine hydrochloride In dichloromethane at 20℃; for 3h;
77.8%
32634-68-7

(2S,3S)-di-4-toluoyltartaric acid

99300-78-4

venlafaxine hydrochloride

(R)-1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol-hemi-D-di-p-toluoyltartrate

Conditions
ConditionsYield
Stage #1: venlafaxine hydrochloride With sodium hydroxide In water; ethyl acetate for 0.25h;
Stage #2: (2S,3S)-di-4-toluoyltartaric acid In methanol; ethyl acetate at 0 - 65℃; for 3.33333h; Heating / reflux;
n/a
99300-78-4

venlafaxine hydrochloride

448904-47-0

desvenlafaxine succinate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water / pH 12 - 13
2.1: sodium thiophenolate / N,N-dimethyl-formamide / 150 - 160 °C
2.2: 0.5 h / 25 - 35 °C / pH 3.5
3.1: water; acetone / 57 - 63 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / dichloromethane; water / 25 - 35 °C / pH 12 - 13
2.1: sodium thiophenolate / N,N-dimethyl-formamide / 155 °C
2.2: 2 h / 25 - 35 °C / pH 3.5
2.3: 0.5 h / pH 9 - 9.5
3.1: water; acetone / 0 - 60 °C / Inert atmosphere
View Scheme
99300-78-4

venlafaxine hydrochloride

C17H25NO

Conditions
ConditionsYield
In methanol for 35.33h; Irradiation;850 mg
99300-78-4

venlafaxine hydrochloride

A

(R)-1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol-hemi-D-di-p-toluoyltartrate

B

C17H27NO2*C20H18O8

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water
2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux
2.2: 0.5 h / Resolution of racemate; Reflux
View Scheme
99300-78-4

venlafaxine hydrochloride

93413-44-6, 93413-69-5, 131801-71-3, 93413-46-8

(R)-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water
2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux
2.2: 0.5 h / Resolution of racemate; Reflux
3.1: sodium hydroxide / water
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water; ethyl acetate / 0.25 h
1.2: 3.33 h / 0 - 65 °C / Heating / reflux
2.1: sodium hydroxide / tert-butyl methyl ether; water / 0.25 h
View Scheme
99300-78-4

venlafaxine hydrochloride

C17H27NO2*C20H18O8

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water
2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux
2.2: 0.5 h / Resolution of racemate; Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water
2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux
2.2: 0.5 h / Resolution of racemate; Reflux
3.1: sodium hydroxide / water
4.1: tetrahydrofuran
View Scheme
99300-78-4

venlafaxine hydrochloride

2C17H27NO2*C20H18O8

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water
2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux
2.2: 0.5 h / Resolution of racemate; Reflux
View Scheme
99300-78-4

venlafaxine hydrochloride

93413-46-8, 93413-69-5, 131801-71-3, 93413-44-6

(S)-1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water
2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux
2.2: 0.5 h / Resolution of racemate; Reflux
3.1: sodium hydroxide / water
View Scheme
99300-78-4

venlafaxine hydrochloride

93413-45-7

(+)-Venlafaxine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water
2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux
2.2: 0.5 h / Resolution of racemate; Reflux
3.1: sodium hydroxide / water
4.1: hydrogenchloride / ethyl acetate
View Scheme
99300-78-4

venlafaxine hydrochloride

142761-11-3

(R)-4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; ethyl acetate / 0.25 h
1.2: 3.33 h / 0 - 65 °C / Heating / reflux
2.1: sodium hydroxide / tert-butyl methyl ether; water / 0.25 h
3.1: lithium diphenylphosphide / tetrahydrofuran / 24 h / 50 °C
3.2: 0.25 h / 22 °C
3.3: pH 9.5
View Scheme
99300-78-4

venlafaxine hydrochloride

1049700-94-8

(-)-O-desmethylvenlafaxine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water; ethyl acetate / 0.25 h
1.2: 3.33 h / 0 - 65 °C / Heating / reflux
2.1: sodium hydroxide / tert-butyl methyl ether; water / 0.25 h
3.1: lithium diphenylphosphide / tetrahydrofuran / 24 h / 50 °C
3.2: 0.25 h / 22 °C
3.3: pH 9.5
4.1: hydrogenchloride / water / 1 h / 0 - 60 °C
View Scheme
Downstream Products
93413-69-5
93413-62-8
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    Venlafaxine hydrochloride

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    1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-1-cyclohexanol hydrochloride

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    Venlafaxine hydrochloride

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Chemistry

Molecular structure of Venlafaxine hydrochloride (CAS NO.99300-78-4) is:

Product Name: Venlafaxine hydrochloride
CAS Registry Number: 99300-78-4
IUPAC Name: 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-olhydrochloride
Molecular Weight: 313.86272 [g/mol]
Molecular Formula: C17H28ClNO2
H-Bond Donor: 2
H-Bond Acceptor: 3
Melting Point: 207-209 °C
Flash Point: 194.2 °C
Enthalpy of Vaporization: 68.34 kJ/mol
Boiling Point: 397.6 °C at 760 mmHg
Vapour Pressure: 4.92E-07 mmHg at 25°C
Product Categories: Active Pharmaceutical Ingredients;Medicine intermediate;Antidepressant;APIs;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Serotonin receptor 

Uses

 Venlafaxine hydrochloride (CAS NO.99300-78-4) can be used as a selective serotonin noradrenaline reuptake inhibitor and also used as an antidepressant. And, it is used primarily for the treatment of major depression in adults.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 1071ug/kg (1.071mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Journal of Toxicology, Clinical Toxicology. Vol. 35, Pg. 211, 1997.
man TDLo oral 32mg/kg/9W-I (32mg/kg) BEHAVIORAL: HEADACHE

BEHAVIORAL: WITHDRAWAL
Medical Journal of Australia. Vol. 169, Pg. 91, 1998.
women LDLo oral 168mg/kg (168mg/kg) BEHAVIORAL: COMA

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Medical Journal of Australia. Vol. 169, Pg. 445, 1998.
women LDLo oral 235mg/kg/12D- (235mg/kg) LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

GASTROINTESTINAL: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Journal of Analytical Toxicology. Vol. 20, Pg. 266, 1996.
women TDLo oral 94500ug/kg/9W (94.5mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Annals of Pharmacotherpy. Vol. 33, Pg. 1009, 1999.
women TDLo oral 315mg/kg/30W- (315mg/kg) BEHAVIORAL: WITHDRAWAL

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Medical Journal of Australia. Vol. 169, Pg. 91, 1998.
women TDLo oral 360mg/kg/17W- (360mg/kg) BEHAVIORAL: WITHDRAWAL

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Medical Journal of Australia. Vol. 169, Pg. 91, 1998.
 

Safety Profile

Hazard Codes: IrritantXi
Risk Statements 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.

Specification

 Venlafaxine hydrochloride , its cas register number is 99300-78-4. It also can be called (+/-)-1-(alpha-((Dimethylamino)methyl)-p-methoxybenzyl)cyclohexanol hydrochloride ; (RS)-1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride ; Effexor .It is a white crystalline powder.