(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}-2-methylpropyl)dimethylamine

• ChemBase ID: 607
• Molecular Formular: C20H26N2
• Molecular Mass: 294.43384
• Monoisotopic Mass: 294.20959884
• SMILES: N1(CC(CN(C)C)C)c2c(CCc3c1cccc3)cccc2
• Canonical SMILES: CN(CC(CN1c2ccccc2CCc2c1cccc2)C)C
• InChI: InChI=1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3
• InChIKey: ZSCDBOWYZJWBIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}-2-methylpropyl)dimethylamine; (3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}-2-methylpropyl)dimethylamine
• IUPAC Traditional name: trimipramine
• Brand Name: Sapilent; Surmontil; Surmontyl; Temaril
• Synonyms: Trimipramina [INN-Spanish]; Trimeprimine; Trimeprimina [Italian]; beta-Methylimipramine; Trimipraminum [INN-Latin]; Trimipramine

Database IDs

• CAS Number: 739-71-9
• PubChem SID: 46507121; 160964070
• PubChem CID: 5584
• CHEBI ID: 9738
• ATC CODE: N06AA10
• CHEMBL: 644
• Chemspider ID: 5382
• DrugBank ID: DB00726
• KEGG ID: D00394
• Unique Ingredient Identifier: 6S082C9NDT
• Wikipedia Title: Trimipramine
• Medline Plus: a602010

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3963908
• LogD (pH = 7.4): 2.746556
• Log P: 4.757892
• Molar Refractivity: 95.022 cm^3
• Polarizability: 36.51729 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.67
• LOG S: -4.05
• Solubility (Water): 2.60e-02 g/l

PROPERTIES

Physical Property

• Solubility: Slightly soluble
• Hydrophobicity(logP): 4.2

Pharmacology Properties

• Admin Routes: Oral, IM, IV
• Bioavailability: 40%
• Excretion: Renal
• Half Life: 11-23 hours
• Metabolism: Hepatic
• Legal Status: Rx-only
• Pregnancy Category: C

DETAILS

DrugBank - DB00726

• Drug Groups: approved
• Description: Tricyclic antidepressant similar to imipramine, but with more antihistaminic and sedative properties. [PubChem]
• Indication: For the treatment of depression and depression accompanied by anxiety, agitation or sleep disturbance
• Pharmacology: Trimipramine is a tricyclic antidepressant. It was thought that tricyclic antidepressants work by inhibiting the re-uptake of the neurotransmitters norepinephrine and serotonin by nerve cells. However, this response occurs immediately, yet mood does not lift for around two weeks. It is now thought that changes occur in receptor sensitivity in the cerebral cortex and hippocampus. The hippocampus is part of the limbic system, a part of the brain involved in emotions. Presynaptic receptors are affected: a1 and b1 receptors are sensitized, a2 receptors are desensitised (leading to increased noradrenaline production). Tricyclics are also known as effective analgesics for different types of pain, especially neuropathic or neuralgic pain. A precise mechanism for their analgesic action is unknown, but it is thought that they modulate anti-pain opioid systems in the CNS via an indirect serotonergic route. They are also effective in migraine prophylaxis, but not in abortion of acute migraine attack. The mechanism of their anti-migraine action is also thought to be serotonergic.
• Toxicity: Side effects include agitation, coma, confusion, convulsions, dilated pupils, disturbed concentration, drowsiness, hallucinations, high fever, irregular heart rate, low body temperature, muscle rigidity, overactive reflexes, severely low blood pressure, stupor, vomiting
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Rapid absorption
• Half Life: 11-18 hrs
• Protein Binding: 93%-96% (to plasma proteins)
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com