trimipramine

Modify Date: 2024-01-02 13:06:20

trimipramine Structure
trimipramine structure
Common Name trimipramine
CAS Number 739-71-9 Molecular Weight 294.43400
Density 0.9912 (rough estimate) Boiling Point 426.2°C (rough estimate)
Molecular Formula C20H26N2 Melting Point 45°
MSDS N/A Flash Point 9℃
Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger

 Use of trimipramine


Trimipramine is a 5-HT receptor antagonist, with pKi binding values of 6.39, 8.10, 4.66 for 5-HT1C, 5-HT2 and 5-HT1A, respectively. Trimipramine is also a potent and selective inhibitor targeting human noradrenaline (hNAT), serotonin (hSERT) and organic cation transporters (hOCT1, hOCT2) with IC50 values of 4.99 μM, 2.11 μM, 3.72 μM, 8.00 μM, respectively. Trimipramine has vascular activity and anxiolytic efficacy[1][2][3].

 Names

Name trimipramine
Synonym More Synonyms

 trimipramine Biological Activity

Description Trimipramine is a 5-HT receptor antagonist, with pKi binding values of 6.39, 8.10, 4.66 for 5-HT1C, 5-HT2 and 5-HT1A, respectively. Trimipramine is also a potent and selective inhibitor targeting human noradrenaline (hNAT), serotonin (hSERT) and organic cation transporters (hOCT1, hOCT2) with IC50 values of 4.99 μM, 2.11 μM, 3.72 μM, 8.00 μM, respectively. Trimipramine has vascular activity and anxiolytic efficacy[1][2][3].
Related Catalog
Target

5-HT1C Receptor:6.39 (pKi)

5-HT2 Receptor:8.10 (pKi)

5-HT1A Receptor:4.66 (pKi)

In Vitro Trimipramine displays much higher affinity for 5-HT2 than for 5-HT1C receptors[1]. Trimipramine is a moderate inhibitor of the human NAT and SERT, with the IC50 values of 4.99 μM and 2.11 μM, respectively[2]. SERT and NAT could represent a target for the antidepressant effects of trimipramine (1 mM, 0.1 mM, 0.01 mM, 1 μM, 0.1 μM; 10 min; HEK293 cells)[2].
In Vivo Trimipramine (5 mg/kg/d; 14 d; chronic administration) acts as functions in rats:1. Increasing concentration of regional 5-HT. 5-HT is highest in the frontal cortex and the hippocampus, followed by the olfactory tubercles and the hypothalamus. 2. Decreasing the number of frontal cortex 5-HT2 and striatal DA D2 receptors. 3. Increasing in the brain regional level of monoamines and metabolites. thus indicates a greater synthesis rate for dopamine (DA) and 5-HT coinciding with an adaptive down regulation of 5-HT2 and DA D2 receptors[3]. Animal Model: Male Wistar rats (220-250 g); implanted osmotic minipump subcutaneously in the dorsal thoracic interscapular region[3] Dosage: 5 mg/kg/day Administration: Delivered by smotic minipump; 14 days Result: Decreased the number of frontal cortex 5-HT2 and striatal DA D2 receptors, thus blocked the uptake of 5-HT and dopamine (DA).
References

[1]. Jenck F, et al. Evidence for a role of 5-HT1C receptors in the antiserotonergic properties of some antidepressant drugs. Eur J Pharmacol. 1993 Feb 9. 231(2):223-9.

[2]. Haenisch B, et al. Inhibitory potencies of trimipramine and its main metabolites at human monoamine and organic cation transporters. Psychopharmacology (Berl). 2011 Sep. 217(2):289-95.

[3]. Juorio AV, et al. The effects of chronic trimipramine treatment on biogenic amine metabolism and on dopamine D2, 5-HT2 and tryptamine binding sites in rat brain. Gen Pharmacol. 1990. 21(5):759-62.

 Chemical & Physical Properties

Density 0.9912 (rough estimate)
Boiling Point 426.2°C (rough estimate)
Melting Point 45°
Molecular Formula C20H26N2
Molecular Weight 294.43400
Flash Point 9℃
Exact Mass 294.21000
PSA 6.48000
LogP 4.18600
Index of Refraction 1.6450 (estimate)
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HO1225000
CHEMICAL NAME :
5H-Dibenz(b,f)azepine, 5-(3-(dimethylamino)-2-methylpropyl)-10,11-dihydro-
CAS REGISTRY NUMBER :
739-71-9
BEILSTEIN REFERENCE NO. :
1321466
LAST UPDATED :
199612
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C20-H26-N2
MOLECULAR WEIGHT :
294.48
WISWESSER LINE NOTATION :
T C676 BN&T&J B1Y1&1N1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
18 mg/kg
TOXIC EFFECTS :
Cardiac - other changes
REFERENCE :
PSDTAP Proceedings of the European Society for the Study of Drug Toxicity. (Princeton, NJ 08540) V.1-15, 1963-74. For publisher information, see PESTD5. Volume(issue)/page/year: 6,171,1965
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 102,753,1963
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
145 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 155,307,1961
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 102,753,1963
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
42 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 155,307,1961

 Safety Information

Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger
Hazard Statements H225-H301 + H311 + H331-H370
Precautionary Statements P210-P260-P280-P301 + P310-P311
Hazard Codes F,T
Risk Phrases 11-23/24/25-39/23/24/25
Safety Phrases 16-36/37-45
RIDADR UN 3249
Packaging Group III
Hazard Class 6.1(b)

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 Synonyms

(+-)-1-cyclohexyl-1-phenyl-3-piperidino-propan-1-ol,hydrochloride
(+-)-1-Cyclohexyl-1-phenyl-3-piperidino-propan-1-ol,Hydrochlorid
tremin
(+/-)-Trihexyphenidyl hydrochloride
EINECS 212-008-3
Trihexy
5-(3-dimethylamino-2-methylpropyl)-10,11-dihydro-5H-dibenz (b,f) azepine acid maleate
triiodothyronine
Trimipramine
paralest
8-Chloro-3-methoxy-11-(1-methyl-4-piperidinyl)-6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-ol
[3-(10,11-dihydro-dibenzo[b,f]azepin-5-yl)-2-methyl-propyl]-dimethyl-amine
10,11-dihydro-5-(3-dimethylamino-2-methylpropyl)-5H-dibenz(b,f)azepine
peragit
Sedrina
timipramine
cyclodol
trihexylphenidyl HCl
pacitane
Broflex
3,3',5-triiodothyronine
L-3,3',5-triiodothyronine
3,5,3'-triiodothyronine
pipanol
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