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56775-88-3 molecular structure
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[(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 and InChIs

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

Cite this record

CBID:4376 http://www.chembase.cn/molecule-4376.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
Z435000 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.5005663  LogD (pH = 7.4) 2.2696636 
Log P 3.508837  Molar Refractivity 93.9379 cm3
Polarizability 32.2363 Å3 Polar Surface Area 16.13 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 3.39  LOG S -4.12 
Solubility (Water) 2.39e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethan expand Show data source
Methanol expand Show data source
Apperance
Tan Oil expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
Oral expand Show data source
Half Life
8.4 +/- 2.0 hours (parent compound)
19.4 +/- 3.6 hours (norzimelidine)
expand Show data source
Legal Status
Withdrawn worldwide expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB04832 external link
Item Information
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 external link
Serotonin uptake inhibitor. Antidepressant.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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