[(2Z)-3-(4-bromophenyl)-3-(pyridin-3-yl)prop-2-en-1-yl]dimethylamine

• ChemBase ID: 4376
• Molecular Formular: C16H17BrN2
• Molecular Mass: 317.22358
• Monoisotopic Mass: 316.05751055
• SMILES: Brc1ccc(C(=CCN(C)C)c2cccnc2)cc1
• Canonical SMILES: CN(CC=C(c1cccnc1)c1ccc(cc1)Br)C
• InChI: InChI=1S/C16H17BrN2/c1-19(2)11-9-16(14-4-3-10-18-12-14)13-5-7-15(17)8-6-13/h3-10,12H,11H2,1-2H3
• InChIKey: OYPPVKRFBIWMSX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2Z)-3-(4-bromophenyl)-3-(pyridin-3-yl)prop-2-en-1-yl]dimethylamine; [3-(4-bromophenyl)-3-(pyridin-3-yl)prop-2-en-1-yl]dimethylamine
• IUPAC Traditional name: zimelidine; zelmid
• Synonyms: (Z)-3-(4-Bromophenyl)-N,N-dimethyl-3-(3-pyridinyl)-2-propen-1-amine; Zimelidine; Zimeldine; (Z)-3-(4'-Bromophenyl)-3-(3''-pyridyl)dimethylallylamine; (Z)-3-[1-(p-Bromophenyl)-3-(dimethylamino)propenyl]pyridine; (z)-zimelidine; Cis-zimelidine; Zimeldine; Zimelidine

Database IDs

• CAS Number: 56775-88-3
• PubChem SID: 46504589; 160967808
• PubChem CID: 5365247; 41987
• ATC CODE: N06AB02
• CHEMBL: 37744
• Chemspider ID: 4517305
• DrugBank ID: DB04832
• Unique Ingredient Identifier: 3J928617DW
• Wikipedia Title: Zimelidine

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.5005663
• LogD (pH = 7.4): 2.2696636
• Log P: 3.508837
• Molar Refractivity: 93.9379 cm^3
• Polarizability: 32.2363 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.39
• LOG S: -4.12
• Solubility (Water): 2.39e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethan; Methanol
• Apperance: Tan Oil

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 8.4 +/- 2.0 hours (parent compound); 19.4 +/- 3.6 hours (norzimelidine)
• Legal Status: Withdrawn worldwide

DETAILS

DrugBank - DB04832

• Drug Groups: withdrawn
• Description: Zimelidine has been banned worldwide due to serious, sometimes fatal, cases of central and/or peripheral neuropathy known as Guillain-Barré syndrome and due to a peculiar hypersensitivity reaction involving many organs including skin exanthema, flu-like symptoms, arthralgias, and sometimes eosinophilia. Additionally, zimelidine was charged to cause an increase in suicidal ideation and/or attempts among depressive patients. After its ban, it was succeeded by fluvoxamine and fluoxetine (derived from the antihistamine diphenhydramine) in that order, and the other SSRIs.
• Indication: For the treatment of depression.
• Pharmacology: Zimelidine was the first marketed selective serotonin reuptake inhibitor (SSRI) antidepressant. It is a pyridylallylamine, structurally different from other antidepressants.
• Affected Organisms: Humans and other mammals
• Half Life: 8.4 +/- 2.0 hours for the parent compound and 19.4 +/- 3.6 hours for norzimelidine.
• References: Caille G, Kouassi E, de Montigny C: Pharmacokinetic study of zimelidine using a new GLC method. Clin Pharmacokinet. 1983 Nov-Dec;8(6):530-40. [Pubmed] ; Godbout R, Montplaisir J: The effect of zimelidine, a serotonin-reuptake blocker, on cataplexy and daytime sleepiness of narcoleptic patients. Clin Neuropharmacol. 1986;9(1):46-51. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - Z435000

Serotonin uptake inhibitor. Antidepressant.

REFERENCES

• Caille G, Kouassi E, de Montigny C: Pharmacokinetic study of zimelidine using a new GLC method. Clin Pharmacokinet. 1983 Nov-Dec;8(6):530-40. Pubmed
• Godbout R, Montplaisir J: The effect of zimelidine, a serotonin-reuptake blocker, on cataplexy and daytime sleepiness of narcoleptic patients. Clin Neuropharmacol. 1986;9(1):46-51. Pubmed
• Brown, D., et al.: Eur. J. Clin Pharmacol., 17, 111 (1980)
• Heel, R.C, Drugs, 24, 169 (1980)