Melitracen hydrochloride

Names

[ Name ]:
Melitracen hydrochloride

[Synonym ]:
3-(10,10-Dimethyl-9(10H)-anthracenylidene)-N,N-dimethyl-1-propanamine Hydrochloride
9,10-Dihydro-10,10-dimethyl-9-(3-dimethylaminopropylidene)anthracene Hydrochloride
U 24973A
EINECS 234-150-5
Thymeol hydrochloride
N,N-Dimethyl-3-(10,10-dimethyl-9(10H)-anthrylidene)propylamine Hydrochloride
3-(10,10-Dimethyl-9(10H)-anthracenylidene)-N,N-dimethyl-1-propanamine hydrochloride (1:1)
9-[3-(Dimethylamino)propylidene]-10,10-dimethyl-9,10-dihydroanthracene Hydrochloride
Dixeran
Melitracene hydrochloride
U-24,973A
MELITRACEN HYDROCHLORIDE
Melitracen HCl
3-(10,10-Dimethylanthracen-9(10H)-ylidene)-N,N-dimethylpropan-1-amine hydrochloride (1:1)
N 7001
Trausabun
N,N,10,10-Tetramethyl-D9(10H),g-anthracenepropylamine Hydrochloride
1-Propanamine, 3-(10,10-dimethyl-9(10H)-anthracenylidene)-N,N-dimethyl-, hydrochloride (1:1)

Biological Activity

[Description]:

Melitracen hydrochloride is an orally active biphasic antidepressant and antianxiety agent. Melitracen hydrochloride can inhibit the uptake of Norepinephrine and 5-HT (serotonin) through the presynaptic membrane inducing the increase of monoamine transmitters in synaptic space[1][2].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

5-HT receptor[1]

[In Vivo]

Single oral administration of either Imipramine or Melitracen produces a marked and long lasting mydriasis in mice. The mydriatic effect of Melitracen is more marked and longer lasting. Melitracen is more effective with respect to behavioral excitement. Single oral administration of Melitracen produces lowering of the catechol amine levels in the brain stem, the cerebral cortex, the spleen, and the adrenals[2]. No significant changes in catecholamine levels of the brain stem, the cerebral cortex, and the spleen were observed in rats receiving daily doses of Melitracen for 13 and 15 weeks. The adrenalin level in the adrenals, however, is slightly decreased[2].

[References]

[1]. Xiaoqian Zhou , et al. The Efficacy of Flupentixol-Melitracen in the Adjuvant Therapy of Ulcerative Colitis in the Chinese Population: A Meta-Analysis. Gastroenterol Res Pract. 2019 Feb 28;2019:3480732.

[2]. K Shimamoto, et al. Myriatic Effect of 9-(gamma-dimethylamino-propylidene)-10, 10-diemthyl-9, 10-dihydroanthracene Hydrochloride (Melitracen) in Mice and Rats. Acta Sch Med Univ Kioto. 1967 Jul;40(1):38-47.

Chemical & Physical Properties

[ Density]:
1.046 g/cm3

[ Boiling Point ]:
399.1ºC at 760 mmHg

[ Melting Point ]:
245-248ºC

[ Molecular Formula ]:
C₂₁H₂₆ClN

[ Molecular Weight ]:
327.891

[ Flash Point ]:
174.4ºC

[ Exact Mass ]:
327.175385

[ PSA ]:
3.24000

[ LogP ]:
5.51130

[ Vapour Pressure ]:
1.4E-06mmHg at 25°C

[ Index of Refraction ]:
1.607

[ Storage condition ]:
Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CB0875000

CHEMICAL NAME :: delta(sup 9(10H)),gamma-Anthracenepropylamine, N,N,10,10-tetramethyl-, hydrochloride

CAS REGISTRY NUMBER :: 10563-70-9

LAST UPDATED :: 199604

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C21-H25-N.Cl-H

MOLECULAR WEIGHT :: 327.93

WISWESSER LINE NOTATION :: L C666 BY IHJ BU3N1&1 I1 I1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 170 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,80,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 96 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,80,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 760 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,390,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 315 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,80,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 131 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,80,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 275 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,390,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 52 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 24,121,1966

Related Compounds

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