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

• ChemBase ID: 72681
• Molecular Formular: C17H28ClNO2
• Molecular Mass: 313.86272
• Monoisotopic Mass: 313.18085682
• SMILES: C1CCCCC1(C(CN(C)C)c1ccc(cc1)OC)O.Cl
• Canonical SMILES: COc1ccc(cc1)C(C1(O)CCCCC1)CN(C)C.Cl
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol hydrochloride
• IUPAC Traditional name: venlafaxine hydrochloride; 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol hydrochloride
• Synonyms: 1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol Hydrochloride; D,L-Venlafaxine, Hydrochloride; (+/-)-1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride; Venlafaxine hydrochloride; Effexor; Effexor XR; Efexor; Venlafaxine hydrochloride; Venlafaxine 盐酸盐

Database IDs

• CAS Number: 99300-78-4
• MDL Number: MFCD03658865
• PubChem SID: 162037602
• PubChem CID: 62923

CALCULATED PROPERTIES

• Acid pKa: 14.420212
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.412785
• LogD (pH = 7.4): 1.221672
• Log P: 2.7385228
• Molar Refractivity: 83.0242 cm^3
• Polarizability: 32.606743 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; H2O: >10 mg/mL; Methanol
• Apperance: white powder; White Solid
• Melting Point: 207-209°C

Safety Information

• Storage Condition: -20°C; protect from light; Refrigerator
• RTECS: GV8872760
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: 5-HT receptor
• Mechanism of Action: 5HT Uptake inhibitor; Serotonin-norepinephrine reuptake inhibitor (SNRI)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: HCl; Hydrochloride
• Application(s): Antidepressant for the treatment of clinical depression and anxiety disorders
• Empirical Formula (Hill Notation): C17H27NO2 · HCl

DETAILS

Selleck Chemicals - S1441

Research Area: Neurological Disease
Biological Activity:
Venlafaxine is an arylalkanolamine serotonin-norepinephrine reuptake inhibitor (SNRI). It is surprisingly effective in treating depression in heroin and other opioid addicts compared to all other conventional antidepressants. In children and adolescents, venlafaxine (like other antidepressants) has a potential to increase suicidal thoughts, attempts and events of self-harm. [1]

Sigma Aldrich - V7264

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.

Toronto Research Chemicals - V120000

A selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant.

REFERENCES

• http://www.rxlist.com/effexor-drug.htm
• Klamerus, K. J., et al.: J. Clin. PHarmacol., 32, 716 (1992)
• Gelenberg, A.J., et al.: J. Am. Med. Assoc., 283, 3082 (2000)
• Eur. Pat., 1984, American Home Products, 112 669; CA, 102, 5895e, (pmr, synth, pharmacol)
• Muth, E.A. et al., Biochem. Pharmacol., 1986, 35, 4493, (pharmacol)
• Fabre, L.F. et al., Curr. Ther. Res., 1987, 42, 901, (adverse effects)
• Yardley, J.P. et al., J. Med. Chem., 1990, 33, 2899, (synth, activity)
• Klamerus, K.J. et al., J. Clin. Pharmacol., 1992, 32, 716, (pharmacokinet)
• Phase III Drug Prof., 1993, 3, 16, (rev)
• Hicks, D.R. et al., Ther. Drug Monit., 1994, 16, 100, (hplc)
• Howell, S.R. et al., Xenobiotica, 1994, 24, 315, (pharmacokinet)
• Holliday, S.M. et al., Drugs, 1995, 49, 280, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 311