| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-06-03 10:24:35 UTC |
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| Update Date | 2016-11-09 01:22:49 UTC |
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| Accession Number | CHEM042901 |
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| Identification |
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| Common Name | zimeldine |
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| Class | Small Molecule |
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| Description | Zimelidine (INN, BAN) (brand names Zimeldine, Normud, Zelmid) was one of the first selective serotonin reuptake inhibitor (SSRI) antidepressants to be marketed. It is a pyridylallylamine, and is structurally different from other antidepressants.Zimelidine was developed in the late 1970s and early 1980s by Arvid Carlsson, who was then working for the Swedish company Astra AB. It was discovered following a search for drugs with structures similar to brompheniramine (it is a derivative of brompheniramine), an antihistamine with antidepressant activity. Zimelidine was first sold in 1982.While zimelidine had a very favorable safety profile, within a year and a half of its introduction, rare case reports of Guillain–Barré syndrome emerged that appeared to be caused by the drug, prompting its manufacturer to withdraw it from the market. After its withdrawal, it was succeeded by fluvoxamine and fluoxetine (derived from the antihistamine diphenhydramine) in that order, and the other SSRIs. |
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| Contaminant Sources | |
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| Zimeldine hydrochloride | MeSH | | Zimelidine | MeSH | | Zimelidine hydrochloride | MeSH | | Zimelidin | MeSH | | Hydrochloride, zimeldine | MeSH | | Zelmid | MeSH | | Hydrochloride, zimelidine | MeSH | | Normud | ChEMBL |
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| Chemical Formula | C16H17BrN2 |
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| Average Molecular Mass | 317.230 g/mol |
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| Monoisotopic Mass | 316.058 g/mol |
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| CAS Registry Number | 56775-88-3 |
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| IUPAC Name | [(2Z)-3-(4-bromophenyl)-3-(pyridin-3-yl)prop-2-en-1-yl]dimethylamine |
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| Traditional Name | zimelidine |
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| SMILES | [H]\C(CN(C)C)=C(/C1=CC=C(Br)C=C1)C1=CN=CC=C1 |
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| InChI Identifier | 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/b16-9- |
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| InChI Key | OYPPVKRFBIWMSX-SXGWCWSVSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Styrenes |
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| Direct Parent | Styrenes |
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| Alternative Parents | |
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| Substituents | - Styrene
- Bromobenzene
- Halobenzene
- Aryl bromide
- Aryl halide
- Pyridine
- Heteroaromatic compound
- Tertiary aliphatic amine
- Tertiary amine
- Organoheterocyclic compound
- Azacycle
- Hydrocarbon derivative
- Amine
- Organonitrogen compound
- Organobromide
- Organohalogen compound
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0029000000-958e295d7ad47abb8ee2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06di-4196000000-bd78fb6683128026cfd0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aou-3590000000-a7678dd2fe8902783899 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0009000000-5c6ca72281628165329f | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0029000000-814b11d75f38254bcab5 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-054o-3390000000-bb94926701304ef0971f | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Zimelidine |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 5365247 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | Not Available |
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