Dimemorfan phosphate

Modify Date: 2024-01-03 16:36:54

Dimemorfan phosphate structure	Common Name	Dimemorfan phosphate
	CAS Number	36304-84-4	Molecular Weight	353.393
	Density	1.07g/cm3	Boiling Point	366.9ºC at 760mmHg
	Molecular Formula	C₁₈H₂₈NO₄P	Melting Point	N/A
	MSDS	N/A	Flash Point	158.3ºC

Use of Dimemorfan phosphate

Dimemorfan phosphate is a sigma 1 receptor agonist, used as a potent antitussive.

Name	Dimemorfan phosphate
Synonym	More Synonyms

Description	Dimemorfan phosphate is a sigma 1 receptor agonist, used as a potent antitussive.
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Sigma Receptor Research Areas >> Neurological Disease Research Areas >> Inflammation/Immunology
In Vitro	Dimemorfan (5-20 μM) inhibits both fMLP- and PMA-induced ROS production in a concentration-dependent manner and is relatively more potent in inhibiting fMLP-induced ROS production with an IC50 value of 7.0 μM. Dimemorfan (10-50 μM) does not display significant activity in scavenging free radicals by xanthine/xanthine oxidase system. Dimemorfan significantly suppressed Mac-1 upregulation both in PMA- and fMLP-activated groups. Dimemorfan (10-20 μM) significantly suppresses LPS-induced ROS and NO production, and suppresses LPS-induced iNOS protein expression, and both the percentage of the positively stained population and the MCF intensities of MCP-1 and TNF-α in BV2 cytosol. Dimemorfan (20 μM) significantly blocks the degradation of cytosolic Iκ-Bα and nuclear translocation of NF-κB p65, as well as the transcriptional activity of NF-κB[2].
In Vivo	Dimemorfan (6.25 or 12.5 mg/kg, s.c.) significantly attenuates the BAY k-8644-induced convulsive behaviors, in a dose-related manner (6.25 mg/kg dimemorfan+BAY k-8644 or 12.5 mg/kg dimemorfan+BAY k-8644 versus Saline+BAY k-8644, P<0.05 and P<0.01, respectively). Dimemorfan significantly attenuates BAY k-8644-induced increases in the c-fos and c-jun protein expression in a dose-dependent manner. Dimemorfan does not significantly affect locomotor activity or produce significant circling behavior in any locomotor pattern in mice[1]. Dimemorfan (1 and 5 mg/kg, i.p.) surpresses the incarease of the plasma levels of TNF-α in mice. The infiltration of neutrophils into lung and liver as well as the production of oxidative stress (EB staining) in these tissues induced by LPS is markedly inhibited by the treatment with dimemorfan[2].
Animal Admin	C57BL/6 mice receive each morphinan (dextromethorphan, dextrorphan or dimemorfan) compound (20 or 40 mg/kg, i.p. per day) or PCP (2.5 or 5 mg/kg, i.p. per day) once a day for 7 days. Ten minutes after the last treatment with each drug, locomotor activity is measured for 30 min using an automated video-tracking system. Eight test boxes (40 cm×40 cm×30 cm high) are operated simultaneously by an IBM computer. Animals are studied individually during locomotion in each test box, where they are adapted for 10 min before starting the experiment. A printout for each session showed the pattern of the ambulatory movements of the test box. The distance traveled in cm by the animals in horizontal locomotor activity is analyzed. Data are collected and analyzed between 09:00 and 17:00 h.
References	[1]. Shin EJ, et al. Dimemorfan prevents seizures induced by the L-type calcium channel activator BAY k-8644 in mice. Behav Brain Res. 2004 May 5;151(1-2):267-76. [2]. Wang YH, et al. Anti-inflammatory effects of dimemorfan on inflammatory cells and LPS-induced endotoxin shock in mice. Br J Pharmacol. 2008 Jul;154(6):1327-38.

Density	1.07g/cm3
Boiling Point	366.9ºC at 760mmHg
Molecular Formula	C₁₈H₂₈NO₄P
Molecular Weight	353.393
Flash Point	158.3ºC
Exact Mass	353.175598
PSA	90.81000
LogP	2.69250
Storage condition	-20℃

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QC7696000

CAS REGISTRY NUMBER :: 36304-84-4

LAST UPDATED :: 199512

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C18-H25-N.H3-O4-P

MOLECULAR WEIGHT :: 353.44

WISWESSER LINE NOTATION :: T6 G666/FQ 2AF Q FX ONT&TTJ I1 O1 &QPQQO

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 :: 690 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,1207,1972

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 124 mg/kg

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,1207,1972

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 556 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: JMGZAI Japan Medical Gazette. (Tokyo, Japan) V.1-18(?), 1964-81. Discontinued. Volume(issue)/page/year: 11(12),13,1974

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 57500 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,1207,1972

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 475 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,353,1976

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 202 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: JMGZAI Japan Medical Gazette. (Tokyo, Japan) V.1-18(?), 1964-81. Discontinued. Volume(issue)/page/year: 11(12),13,1974

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 33900 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,1207,1972

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 35 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Gastrointestinal - nausea or vomiting

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,353,1976

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 22600 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,1207,1972

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 528 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,1207,1972

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 180 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,1207,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6 gm/kg/5W-I

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - other changes Blood - other changes

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,2069,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 31200 mg/kg/26W-I

TOXIC EFFECTS :: Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,2069,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 12 gm/kg/5W-I

TOXIC EFFECTS :: Liver - fatty liver degeneration Related to Chronic Data - death

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,2102,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 2280 mg/kg/5W-I

TOXIC EFFECTS :: Gastrointestinal - changes in structure or function of salivary glands Liver - fatty liver degeneration

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,2102,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 7500 mg/kg/5W-I

TOXIC EFFECTS :: Liver - fatty liver degeneration Related to Chronic Data - death

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,2102,1972 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 mg/kg

SEX/DURATION :: female 8-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,2089,1972

(14α)-3,17-Dimethylmorphinan phosphate (1:1)

Morphinan, 3,17-dimethyl-, (14α)-, phosphate (1:1)

d-3-Methyl-N-methylmorphinan phosphate

dimemorphan phosphate

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Dimemorfan phosphate

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Dimemorfan phosphate Biological Activity

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CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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