Basic information
- CAS
99300-78-4- Standard SMILES
COc1ccc(C(CN(C)C)C2(O)CCCCC2)cc1.Cl- InChIKey
QYRYFNHXARDNFZ-UHFFFAOYSA-N- Molecular formula
- C17H28ClNO2
- Average molar mass
- 313.9 g/mol
- Monoisotopic mass
- 313.18085682
Overview
Venlafaxine Hydrochloride is a synthetic ethyl-cyclohexanol derivative used for the treatment of depression, Venlafaxine Hydrochloride is metabolized to O-desmethylvenlafaxine, which potentiates CNS activity. Both venlafaxine and its active metabolite inhibit neuronal reuptake of norepinephrine, dopamine, and serotonin. (NCI04)
Names & identifiers
- Preferred name
- Venlafaxine Hydrochloride
- IUPAC
- 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol;hydrochloride
- English name
- Venlafaxine hydrochloride
- Molecular formula
- C17H28ClNO2
- Molecular weight
- 313.86
Names & synonyms
Show more names
Database identifiers
- CAS
99300-78-4- PubChem CID
- 62923
- DTXSID
DTXSID8047397- ChEMBL
CHEMBL1201066- UNII
- 7D7RX5A8MO
- EC Number
- 619-421-1
Properties
Computed structural properties
- Topological polar surface area
- 32.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 279
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 207 · 207-209°C
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: >10mg/mL
- form
- powder
- color
- white
- Water Solubility
- 100 mMDMSO: · water: 100mMDMSO: 50mM
- Merck
- 14 · 14,9946
- BCS Class
- 1 · 1
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C17H27NO2.ClH/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14;/h7-10,16,19H,4-6,11-13H2,1-3H3;1H
- InChIKey
- QYRYFNHXARDNFZ-UHFFFAOYSA-N
- SMILES
- OC1(CCCCC1)C(C1=CC=C(OC)C=C1)CN(C)C.[H]Cl
- CAS DataBase Reference
- 99300 · 99300-78-4(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- Effexor
- FDA UNII
- 7 D7RX5A8MO · 7D7RX5A8MO
- NCI Drug Dictionary
- Effexor
- EPA Substance Registry System
- 1 · Cyclohexanol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-, hydrochloride (1:1 (99300-78-4)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 9 · GHS09
- Signal word
- Danger
- Hazard statements
- 411 · H411
- Precautionary statements
- 273 · P273-P391-P501
- Hazard Codes
- Xi,T,F
- Risk Statements
- 36 · 36/37/38-36-39/23/24/25-23/24/25-11
- Safety Statements
- 26 · 26-37/39-45-36/37-16-7
- RIDADR
- 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
- WGK Germany
- 3 · 3
- RTECS
- 8872760 · GV8872760
- HS Code
- 29225090 · 29225090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Aquatic Chronic 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.9% (1 of 113) of reports.
Warning
H302 (15.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 113 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Toxicology
Treatment
Treatment should consist of those general measures employed in the management of overdosage with any antidepressant. Ensure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion or in symptomatic patients. Activated charcoal should be administered. Due to the large volume of distribution of this drug, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. No specific antidotes for venlafaxine are known. (L1712)
Toxicity Summary
The exact mechanism of action of venlafaxine is unknown, but appears to be associated with the its potentiation of neurotrasmitter activity in the CNS. Venlafaxine and its active metabolite, O-desmethylvenlafaxine (ODV), inhibit the reuptake of both serotonin and norepinephrine with a potency greater for the 5-HT than for the NE reuptake process. Both venlafaxine and the ODV metabolite have weak inhibitory effects on the reuptake of dopamine but, unlike the tricyclics and similar to SSRIs, they are not active at histaminergic, muscarinic, or alpha(1)-adrenergic receptors.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Venlafaxine hydrochloride
vLess-DILI-concern
7
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- rtecs
- GV8872760
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29225090
- risk_code
- 36/37/38-36-39/23/24/25-23/24/25-11
- Signal word
- Danger
- Symbol(GHS)
- GHS09
- hazard_code
- Xi,T,F
- safety_code
- 26-37/39-45-36/37-16-7
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H411
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 2
- Precautionary statements
- P273-P391-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Undergoes extensive first pass metabolism in the liver to its major, active metabolite, ODV, and two minor, less active metabolites, N-desmethylvenlafaxine and N,O-didesmethylvenlafaxine. Formation of ODV is catalyzed by cytochrome P450 (CYP) 2D6, whereas N-demethylation is catalyzed by CYP3A4, 2C19 and 2C9. ODV possesses antidepressant activity that is comparable to that of venlfaxine. Route of Elimination: Renal elimination of venlafaxine and its metabolites is the primary route of excretion. Approximately 87% of a venlafaxine dose is recovered in the urine within 48 hours as either unchanged venlafaxine (5%), unconjugated ODV (29%), conjugated ODV (26%), or other minor inactive metabolites (27%). Half Life: 5 hours
FDA Pharmacological Classification
VENLAFAXINE HCL
Norepinephrine Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Serotonin Uptake Inhibitors [MoA]
VENLAFAXINE HCL ER
Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Norepinephrine Uptake Inhibitors [MoA]
VENLAFAXINE HYDROCHLORIDE
Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Norepinephrine Uptake Inhibitors [MoA]
MeSH Pharmacological Classification
Drugs that selectively block or suppress the plasma membrane transport of SEROTONIN and NORADRENALINE into axon terminals and are used as ANTIDEPRESSIVE AGENTS.
A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.
Uses & manufacturing
Uses
For the management of major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder (social phobia), panic disorder with or without agoraphobia, vasomotor symptoms in women with breast cancer and in postmenopausal women, and neuropathic pain.
Applications
DescriptionVenlafaxine 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.
UsesA selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant
UsesAn inhibitor of ST and SLC6A2.
UsesVenlafaxine 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]
General DescriptionA 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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
Compound notes
Loading…