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Venlafaxine hydrochloride

Synthesis

CAS No.99300-78-4
Chemical Name:Venlafaxine hydrochloride
CBNumber:CB0136181
Molecular Formula:C17H28ClNO2
Formula Weight:313.86
MOL File:99300-78-4.mol

Venlafaxine hydrochloride Property

Melting point 207-209°C
Flash point 9℃
storage temp. 2-8°C
solubility H2O: >10mg/mL
form powder
color white
Water Solubility water: 100mM
DMSO: 50mM
Merck 14,9946
BCS Class 1
InChIKey QYRYFNHXARDNFZ-UHFFFAOYSA-N
CAS DataBase Reference 99300-78-4(CAS DataBase Reference)
NCI Dictionary of Cancer Terms Effexor
FDA UNII 7D7RX5A8MO
NCI Drug Dictionary Effexor
EPA Substance Registry System Cyclohexanol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-, hydrochloride (1:1 (99300-78-4)
UNSPSC Code 41116107
NACRES NA.77

Safety

Hazard Codes :Xi,T,F
Risk Statements :36/37/38-36-39/23/24/25-23/24/25-11
Safety Statements :26-37/39-45-36/37-16-7
RIDADR :UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany :3
RTECS :GV8872760
HS Code :29225090

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H411
Precautionary statements P273-P391-P501

Venlafaxine hydrochloride Price More Price(6)

Brand: Sigma-Aldrich(India)
Product number: V7264
Product name : Venlafaxine hydrochloride
Purity: ≥98% (HPLC), powder
Packaging: 10MG
Price: ₹15598.83
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: V7264
Product name : Venlafaxine hydrochloride
Purity: ≥98% (HPLC), powder
Packaging: 50MG
Price: ₹73350.2
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: V-004
Product name : Venlafaxine hydrochloride solution
Purity: 1.0?mg/mL in methanol (as free base), ampule of 1?mL, certified reference material, Cerilliant?
Packaging: 1ML
Price: ₹8751.4
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: PHR1736
Product name : Venlafaxine Hydrochloride
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1G
Price: ₹11420.38
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: V0110
Product name : Venlafaxine Hydrochloride
Purity:
Packaging: 1G
Price: ₹6100
Updated: 2022/05/26
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Venlafaxine hydrochloride Chemical Properties,Usage,Production

Synthesis Venlafaxine (92.4 g) was dissolved in ethyl acetate (450 ml) at 50-55 ºC, filtered hot then cooled to 10-15 ºC and pH was adjusted to <2 with addition of isopropyl alcohol saturated with HCl gas and allowed to stand for 15 minutes. The white solid was filtered off, washed with EtOAc (75 ml), and then with petroleum ether (150 ml). The crystalline salt was dissolved in MeOH (160 ml) at 50-55 ºC and filtered when hot. The hydrochloride salt 35 was precipitated by adding ethyl acetate drop-wise, at room temperature. After 4 hours the solid was filtered and washed with ethyl acetate (100 ml). The solid (98.3 g) was allowed to dry in air (6-8 hours).
Description Venlafaxine hydrochloride, a novel phenethylamine derivative, was introduced in the U.S.A. as an antidepressant. Venlafaxine is reported to be the first in the class of the second-generation of antidepressants with dual serotonidnorepinephrine reuptake inhibitory activity. Venlafaxine lacks any affinity for muscarinic, cholinergic, histaminergic and noradrenergic receptors and therefore, has an unusually favorable side effect profile compared with classical tricyclic antidepressants and shows less cardiotoxicity. In addition, venlafaxine has a rapid onset of action that makes it unique among the antidepressant agents. Other indications for venlafaxine include the treatment of obsessive and panic disorders, and obesity. Both enantiomers of venlafaxine were reported to have similar biological activity.
Chemical Properties White Crystalline Powder
Originator Wyeth-Ayerst (U.S.A.)
Uses A selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant
Uses Venlafaxine hydrochloride is an inhibitor of reuptake of both serotonin (IC50 = 0.21 μM) and norepinephrine (IC50 = 0.64 μM). It is effective in vitro and in vivo and against human as well as rat receptors. As an antidepressant, it is properly placed in the serotonin-norepinephrine reuptake inhibitor class.[Cayman Chemical]
Uses An inhibitor of ST and SLC6A2.
Manufacturing Process 1-[Cyano(-methoxyphenyl)methyl]cyclohexanol
p-Methoxyphenylacetonitrile (50 gm, 0.3 mole) was added to dry tetrahydrofuran (250 ml) and the solution cooled to -70°C under nitrogen. n- Butyl lithium in hexane (210 ml, 0.3 mole) was added dropwise, with stirring. The temperature was maintained below -50°C and a yellow precipitate appeared. After the addition was complete, the reaction mixture was maintained below -50°C for 30 minutes and cyclohexanone (35 ml, 0.3 mole)was added. After a further 45 minutes below -50°C the temperature was allowed to rise to 0°C and a saturated ammonium chloride solution was added. The layers were separated and the aqueous layer extracted with diethyl ether. The combined organic solution was washed with brine, dried over magnesium sulfate and evaporated. The product crystallized (25.2 gm, melting point 125°-127°C). The structure was confirmed by N.M.R. and mass spectral analysis.
1-[2-Amino-1-(p-methoxyphenyl)ethyl]cyclohexanol
1-[Cyano(p-methoxyphenyl)methyl]cyclohexanol (12 g, 0.05 mole) was dissolved on warming in a mixture of ammonia-ethanol (20% v/v, 250 ml) and hydrogenated in a Parr apparatus over 5% rhodium an alumina (2.8 gm). The catalyst was filtered, washed well with ethanol and the combined filtrate evaporated and dried under vacuum yielding an oil (12 gm). Thin layer chromatography: single spot, ninhydrin positive [chloroform-methanol-acetic acid (80:10:10 v/v)].
1-[-2-Dimethyl-amino)-1-(4-methoxyphenyl)-ethyl]cyclohexanol
1-[2-Amino-1-(p-methoxyphenyl)ethyl]cyclohexanol (12 gm; 0.048 mole) was treated with a mixture of formaldehyde (11 ml), formic acid (14.5 ml, 88%) and water (125 ml) and heated at 100°C for five hours. The reaction mixture was cooled and extracted with ethyl acetate. This extract was discarded. The aqueous residue was cooled in ice, rendered basic by the addition of solid potassium hydroxide, saturated with sodium chloride and extracted 3 times with ethyl acetate. The extract was washed with brine, dried over anhydrous potassium carbonate and evaporated to an oily residue (8 gm). This mixture of products was chromatographed on 1 kg of Mallinckrodt Silicar CC7 silica gel and the progress of the chromatography was monitored by thin layer chromatrography using a system comprising ethanol:2 N ammonia:ethyl acetate:cyclohexane 45:8:100:100 (v/v). Fractions containing the desired product were combined and the hydrochloride salt prepared using 4 N HCl in isopropanol. The yield of the free base was 4.6 gm of 1-[(2-dimethylamino)- 1-(4-methoxyphenyl)ethyl]-cyclohexanol. The hydrochloride (venlafaxine): melting point 215°-217°C. The structure was confirmed by mass spectral analysis and N.M.R. analysis.
brand name Effexor (Wyeth).
Therapeutic Function Antidepressant
General Description A Certified Snap-N-Spike^? Solution suitable for many LC/MS and GC/MS applications from forensic or clinical toxicology analysis to urine drug testing. Also known by the brand name Effexor^?, venlafaxine is an SNRI antidepressant approved for the treatment of major depressive and general anxiety disorders.
Biological Activity Dual serotonin/noradrenalin re-uptake inhibitor that displays ~ 30-fold higher affinity for SERT than NET (K i values are 82 and 2480 nM respectively). Antidepressant; increases swimming and climbing behavior in the forced-swim test in rats.
Biochem/physiol Actions Venlafaxine is an antidepressant. The mechanism of the antidepresant action of venlafaxine in humans is associated with its potentiation of neurotransmitter activity in the CNS. Venlafaxine is a potent inhibitor of neuronal serotonin and norepinephrine reuptake and weak inhibitor of dopamine reuptake. Venlafaxine has no significant activity for muscarinic, histaminergic, or α-1 adrenergic receptors in vitro. Venlafaxine does not possess MAO inhibitor activity.
storage Store at RT