Imipramine hydrochloride

Modify Date: 2024-01-07 11:58:56

Imipramine hydrochloride Structure
Imipramine hydrochloride structure
 Common Name Imipramine hydrochloride
CAS Number 113-52-0 Molecular Weight 316.868
Density 1.041g/cm3 Boiling Point 403.1ºC at 760mmHg
Molecular Formula C19H25ClN2 Melting Point 168-1700C
MSDS USA Flash Point 179.7ºC
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Imipramine hydrochloride


Imipramine hydrochloride inhibits serotonin transporter with an IC50 value of 32 nM in vitro.

 Names

Name imipramine hydrochloride
Synonym More Synonyms

 Imipramine hydrochloride Biological Activity

Description Imipramine hydrochloride inhibits serotonin transporter with an IC50 value of 32 nM in vitro.
Related Catalog
Target

IC50: 32 nM (serotonin)[1]

In Vitro Depression-like behavior is often complicated by chronic pain. Antidepressants including imipramine are widely used to treat chronic pain, but the mechanisms are not fully understood[2]. Imipramine (IC50=32 nM) and desipramine (IC50=160 nM) are found to be potent inhibitors of the human placental serotonin transporter[1].
In Vivo Administration of imipramine reverses social avoidance behavior, significantly increasing the interaction time. 24 days of imipramine treatment in RSD mice significantly decreases stress-induced mRNA levels for IL-6 in brain microglia[3]. Chronic mild stress induces a long-term altered gene expression profile in the prefrontal cortex that is partially reverted by imipramine treatment (10mg/kg, i.p.)[4]. Chronic imipramine administration alteres the amino acid dynamics in the brain. In the striatum, the concentrations of asparagine, glutamine and methionine are significantly increased by chronic imipramine administration. In the thalamus and hypothalamus, chronic imipramine administration significantly decreased the valine concentration[5]. Imipramine reduces pain-related negative emotion without influencing pain and that this effect is diminished by denervation of 5-HT neurons and by anti-BDNF treatment. Imipramine also normalizes derangement of ERK/CREB coupling, which leads to induction of BDNF. This suggests a possible interaction between 5-HT and BDNF[2]. Imipramine treatment counteracts the corticosterone administration-induced increase in the reactivity of rat CA3 hippocampal circuitry to the activation of the 5-HT receptor[6].
Animal Admin Rats: The Wistar (WIS) and Wistar Kyoto (WKY) rats are divided into four groups: (1) a control WIS rat group, (2) an imipramine-treated WIS rat group, (3) a control WKY rat group and (4) an imipramine-treated WKY rat group. Distilled water (10 mL/kg) or imipramine solution (10 mg/10 mL/kg) is orally administered for 28 days except on the day of the open field test, when nothing is administered in order to avoid the acute effect of single administration on the open field test[5]. Mice: C57BL/6 mice subjected to repeated social defeat (RSD), home cage control (HCC) are randomLy selected into four groups: RSD/imipramine, RSD/vehicle, HCC/imipramine, and HCC/vehicle. Mice in the RSD/imipramine received daily intraperitoneal (i.p.) injections of imipramine (20 mg/kg) for 24 days after the 6 cycles of RSD. HCC/imipramine received daily i.p. imipramine at the same dose while RSD/vehicle and HCC/vehicle groups received i.p. injections of vehicle (sodium chloride, 0.9%) for 24 days at the same time point[3].
References

[1]. Balkovetz DF, et al. Evidence for an imipramine-sensitive serotonin transporter in human placental brush-border membranes. J Biol Chem. 1989 Feb 5;264(4):2195-8.

[2]. Yasuda S, et al. Imipramine ameliorates pain-related negative emotion via induction of brain-derived neurotrophic factor. Cell Mol Neurobiol. 2014 Nov;34(8):1199-208.

[3]. Ramirez K, et al. Imipramine attenuates neuroinflammatory signaling and reverses stress-induced social avoidance. Brain Behav Immun. 2015 May;46:212-20.

[4]. Erburu M, et al. Chronic mild stress and imipramine treatment elicit opposite changes in behavior and in gene expression in the mouse prefrontal cortex. Pharmacol BiochemBehav. 2015 Aug;135:227-36.

[5]. Nagasawa M, et al. Chronic imipramine treatment differentially alters the brain and plasma amino acid metabolism in Wistar and Wistar Kyoto rats. Eur J Pharmacol. 2015 Sep 5;762:127-35.

[6]. Tokarski K, et al. Imipramine counteracts corticosterone-induced alterations in the effects of the activation of 5-HT(7) receptors in rat hippocampus. J Physiol Pharmacol. 2009 Jun;60(2):83-8.

 Chemical & Physical Properties

Density 1.041g/cm3
Boiling Point 403.1ºC at 760mmHg
Melting Point 168-1700C
Molecular Formula C19H25ClN2
Molecular Weight 316.868
Flash Point 179.7ºC
Exact Mass 316.170624
PSA 6.48000
LogP 4.74200
Appearance of Characters crystalline | white
Vapour Pressure 6.6E-06mmHg at 25°C
Storage condition 2-8°C
Water Solubility H2O: 50 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HO1925000
CHEMICAL NAME :
5H-Dibenz(b,f)azepine, 5-(3-(dimethylamino)propyl)-10,11-dihydro-, monohydrochloride
CAS REGISTRY NUMBER :
113-52-0
LAST UPDATED :
199706
DATA ITEMS CITED :
41
MOLECULAR FORMULA :
C19-H24-N2.Cl-H
MOLECULAR WEIGHT :
316.91
WISWESSER LINE NOTATION :
T C676 BN&T&J B3N1&1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2143 ug/kg/2D-I
TOXIC EFFECTS :
Behavioral - tremor
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Behavioral - sleep Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Cardiac - other changes Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
27 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - muscle contraction or spasticity Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
70 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Cardiac - pulse rate increase, without fall in BP Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
30 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - paresthesis Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
305 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
72 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
217 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
18 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
275 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
104 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
189 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
27 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
14 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
85 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
190 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
78 mg/kg
TOXIC EFFECTS :
Cardiac - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1575 mg/kg/15W-C
TOXIC EFFECTS :
Brain and Coverings - changes in brain weight Lungs, Thorax, or Respiration - other changes Biochemical - Metabolism (Intermediary) - other proteins
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
285 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating - 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
200 mg/kg
SEX/DURATION :
female 7-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
800 mg/kg
SEX/DURATION :
female 1-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1 gm/kg
SEX/DURATION :
female 7-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
180 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
225 mg/kg
SEX/DURATION :
female 23 day(s) pre-mating female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
210 mg/kg
SEX/DURATION :
female 15-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
65 mg/kg
SEX/DURATION :
female 8-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Effects on Newborn - biochemical and metabolic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
130 mg/kg
SEX/DURATION :
female 8-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
65 mg/kg
SEX/DURATION :
female 8-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
9700 mg/kg
SEX/DURATION :
female 75 day(s) pre-mating female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
9200 mg/kg
SEX/DURATION :
female 10 week(s) pre-mating female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
125 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
165 mg/kg
SEX/DURATION :
female 3-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - physical Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
35 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
DNA inhibition

MUTATION DATA

TEST SYSTEM :
Insect - not otherwise specified
DOSE/DURATION :
10 gm/L
REFERENCE :
JCLBA3 Journal of Cell Biology. (Rockefeller Univ. Press, 1230 York Ave., New York, NY 10003) V.12- 1962- Volume(issue)/page/year: 47,182a,1970 *** REVIEWS *** TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 2,209,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5236 No. of Facilities: 123 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 2577 (estimated) No. of Female Employees: 1421 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Hazard Codes Xn: Harmful;
Risk Phrases R23/25
Safety Phrases 7-16-24-33-45-36-26
RIDADR UN 1230 3/PG 2
WGK Germany 3
RTECS HO1925000

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 Synonyms

Janimine (hydrochloride)
3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine hydrochloride (1:1)
5H-dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-, monohydrochloride
3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine hydrochloride
Imipramine hydrochloride
MFCD00012669
EINECS 204-030-7
5H-Dibenz[b,f]azepine, 5-[3- (dimethylamino)propyl]-10,11-dihydro-, monohydrochloride
3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-aminhydrochlorid
Melipramine hydrochloride
Melipramine HCl
3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine hydrochloride (1:1)
N-(γ-Dimethylaminopropyl)iminodibenzyl hydrochloride
3-(10,11-dihydro-5H-dibenzo[b,f]azépin-5-yl)-N,N-diméthylpropan-1-amine chlorhydrate
Tofranil (hydrochloride)
5H-Dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-, hydrochloride (1:1)
Imipraminehydrochloride
Imipramine (hydrochloride)
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