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Product Name: trimipramine
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739-71-9

739-71-9 structure

Name: trimipramine
Chemical Name: trimipramine
CAS Number: 739-71-9
Molecular Formula: C₂₀H₂₆N₂
Molecular Weight: 294.43400
Catalog: API Nervous system medication Antidepressant, manic
Create Date: 2018-07-21 14:20:12
Modify Date: 2024-01-02 13:06:20
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].

Name	trimipramine
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

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	Research Areas >> Neurological Disease Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor Signaling Pathways >> Anti-infection >> Bacterial
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.

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

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

Symbol	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)

14171-70-1

~92%

739-71-9

Literature: Gowda, Narendra B.; Rao, Gopal Krishna; Ramakrishna, Ramesha A. Tetrahedron Letters, 2010 , vol. 51, # 43 p. 5690 - 5693

494-19-9

23349-86-2

739-71-9

Literature: Somashekar; Nagana Gowda; Ramesha; Khetrapal Magnetic Resonance in Chemistry, 2005 , vol. 43, # 2 p. 166 - 170

Precursor 3
14171-70-1 494-19-9 23349-86-2
DownStream 1
14171-70-1

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