dextromethorphan
Conditions | Yield |
---|---|
With sodium hydroxide In water pH=10; Inert atmosphere; | 100% |
With ammonia In chloroform; water at 20℃; for 1h; | |
With ammonia In methanol at 20℃; for 1h; | |
With sodium hydroxide In water | |
In chloroform at 20℃; for 1h; | 2.88 g |
Conditions | Yield |
---|---|
With sodium hydroxide In chloroform; water for 0.5h; | 97.98% |
dextromethorphan N-oxide hydrochloride
A
(+)-3-methoxymorphinan
B
dextromethorphan
Conditions | Yield |
---|---|
Stage #1: dextromethorphan N-oxide hydrochloride With ferrocene In chloroform at 40℃; for 72h; Stage #2: With sodium hydroxide In chloroform; water | A 92% B 8% |
With ferrocene In chloroform at 40℃; for 40h; Polonovski reaction; Inert atmosphere; | A 92% B 8% |
(+)-2-methyl-1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8-hexahydroisoquinoline
dextromethorphan
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; for 2h; Reagent/catalyst; | 91% |
rac-3-methoxy-17-methyl-morphinane
dextromethorphan
Conditions | Yield |
---|---|
Gewinnung mit Hilfe von Lg-Weinsaeure; | |
Gewinnung mit Hilfe von Lg-Weinsaeure; |
(9α,13α,14α)-3-methoxy-17-methylmorphinan-10-one
A
dextromethorphan
B
ent-3-methoxy-17-methyl-morphinan-10β-ol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether |
(+)-3-methoxy-N-formylmorphinan
dextromethorphan
Conditions | Yield |
---|---|
With methanol; toluene | |
With methanol; toluene |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 5 h / 150 °C 2: POCl3 / benzene / Heating 3: pyridine; tetrahydrofuran / 8 h / 0 °C 4: H2 / Ru(OCOCF3)2<(S)-tolbinap> / methanol / 100 h / 30 °C / 76000.1 Torr View Scheme | |
Multi-step reaction with 5 steps 1.1: diisopropyl-carbodiimide; dmap / dichloromethane / 10 h / 0 - 20 °C 2.1: trichlorophosphate / toluene / 4 h / Reflux 3.1: phenylsilane; pyrrolidine / tetrahydrofuran; methanol / 5 h / 20 °C / Inert atmosphere 4.1: methanol / 0.25 h 4.2: 10 h / 20 °C 5.1: aluminum (III) chloride / dichloromethane / 2 h / 20 °C View Scheme |
1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline
dextromethorphan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine; tetrahydrofuran / 8 h / 0 °C 2: H2 / Ru(OCOCF3)2<(S)-tolbinap> / methanol / 100 h / 30 °C / 76000.1 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: phenylsilane; pyrrolidine / tetrahydrofuran; methanol / 5 h / 20 °C / Inert atmosphere 2.1: methanol / 0.25 h 2.2: 10 h / 20 °C 3.1: aluminum (III) chloride / dichloromethane / 2 h / 20 °C View Scheme |
N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide
dextromethorphan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: POCl3 / benzene / Heating 2: pyridine; tetrahydrofuran / 8 h / 0 °C 3: H2 / Ru(OCOCF3)2<(S)-tolbinap> / methanol / 100 h / 30 °C / 76000.1 Torr View Scheme | |
Multi-step reaction with 4 steps 1.1: trichlorophosphate / toluene / 4 h / Reflux 2.1: phenylsilane; pyrrolidine / tetrahydrofuran; methanol / 5 h / 20 °C / Inert atmosphere 3.1: methanol / 0.25 h 3.2: 10 h / 20 °C 4.1: aluminum (III) chloride / dichloromethane / 2 h / 20 °C View Scheme |
(Z)-2-Formyl-1-<(4-methoxyphenyl)methylene>-1,2,3,4,5,6,7,8-octahydroisoquinoline
dextromethorphan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2 / Ru(OCOCF3)2<(S)-tolbinap> / methanol / 100 h / 30 °C / 76000.1 Torr View Scheme |
(S)-2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline
dextromethorphan
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 5 h / 150 °C 2: POCl3 / benzene / Heating 3: pyridine; tetrahydrofuran / 8 h / 0 °C 4: H2 / Ru(OCOCF3)2<(S)-tolbinap> / methanol / 100 h / 30 °C / 76000.1 Torr View Scheme | |
Multi-step reaction with 5 steps 1.1: diisopropyl-carbodiimide; dmap / dichloromethane / 10 h / 0 - 20 °C 2.1: trichlorophosphate / toluene / 4 h / Reflux 3.1: phenylsilane; pyrrolidine / tetrahydrofuran; methanol / 5 h / 20 °C / Inert atmosphere 4.1: methanol / 0.25 h 4.2: 10 h / 20 °C 5.1: aluminum (III) chloride / dichloromethane / 2 h / 20 °C View Scheme |
dextromethorphan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene; methanol 2: Gewinnung mit Hilfe von Lg-Weinsaeure View Scheme | |
Multi-step reaction with 2 steps 1: methanol; toluene 2: Gewinnung mit Hilfe von Lg-Weinsaeure View Scheme |
Conditions | Yield |
---|---|
Stage #1: tri(4-tolyl)aminium hexafluorophosphate; dextromethorphan With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at -5℃; for 0.0833333h; Inert atmosphere; Stage #2: phenylmagnesium bromide In tetrahydrofuran; acetonitrile at 0℃; for 0.0833333h; Inert atmosphere; regioselective reaction; | A 99% B 83% |
dextromethorphan
(+)-3-methoxymorphinan
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With 3-chloro-benzenecarboperoxoic acid Polonovski type reaction; Inert atmosphere; Stage #2: With iron In chloroform at 20℃; Polonovski type reaction; Inert atmosphere; | 97% |
With BM3 variant 4H5 Enzymatic reaction; | 50% |
With human CYP3A4 expressed in Escherichia coli; NADPH-regenerating system In phosphate buffer for 0.25h; pH=7.4; Enzyme kinetics; Further Variations:; Reagents; |
dextromethorphan
2,2,2-Trichloroethyl chloroformate
1,3,4,9,10,10A-hexahydro-6-methoxy-2H-10,4A-(iminoethano)phenanthrene-11-carboxylic acid
Conditions | Yield |
---|---|
In toluene Heating; | 95% |
In toluene for 2h; Heating; | 91.2% |
dextromethorphan
methyl iodide
ent-3-methoxy-17,17-dimethyl-9,10-didehydro-9,17-seco-morphinane
Conditions | Yield |
---|---|
Stage #1: dextromethorphan; methyl iodide Stage #2: Alkaline hydrolysis; | 95% |
dextromethorphan
dextromethorphan N-oxide
Conditions | Yield |
---|---|
With perfluoro-cis-2-n-butyl-3-n-propyloxaziridine; HCFC-225ca,cb In dichloromethane at -60℃; for 0.333333h; | 94% |
With methanol; water; dihydrogen peroxide | |
With dihydrogen peroxide In methanol at 20℃; for 48h; |
dextromethorphan
dextromethorphan N-oxide hydrochloride
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With m-CPBA In chloroform at -30 - -20℃; Stage #2: With sodium hydroxide In chloroform; water Stage #3: With hydrogenchloride In chloroform; water | 94% |
Stage #1: dextromethorphan With dihydrogen peroxide In methanol; water at 0 - 20℃; for 18h; Stage #2: With hydrogenchloride In water | 94% |
dextromethorphan
[2H]-Dextromethorphan 17-d3
Conditions | Yield |
---|---|
With deuterium In tetrahydrofuran for 36h; Glovebox; Inert atmosphere; regioselective reaction; | 92% |
Conditions | Yield |
---|---|
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; sodium acetate In N,N-dimethyl-formamide at 20℃; for 16h; Irradiation; Inert atmosphere; diastereoselective reaction; | 86% |
dextromethorphan
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With carbonochloridic acid 1-chloro-ethyl ester In toluene at 20℃; for 1h; Stage #2: With methanol In toluene at 65℃; for 1h; Reflux; | 84.1% |
1,4-diaza-bicyclo[2.2.2]octane
sodium hydrogencarbonate
dextromethorphan
B
(+)-3-methoxymorphinan
Conditions | Yield |
---|---|
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; dextromethorphan With tri(4-tolyl)aminium hexafluorophosphate In acetonitrile at -5℃; for 0.0833333h; Inert atmosphere; Stage #2: sodium hydrogencarbonate With water chemoselective reaction; | A 8% B 83% |
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With 1,4-diaza-bicyclo[2.2.2]octane; tri(4-tolyl)aminium hexafluorophosphate In acetonitrile at -5℃; for 0.0833333h; Inert atmosphere; Stage #2: ethylmagnesium bromide In diethyl ether; acetonitrile at 0℃; for 0.0833333h; Inert atmosphere; regioselective reaction; | 81% |
Conditions | Yield |
---|---|
With SoLo unspecific peroxygenase In aq. phosphate buffer; acetonitrile at 30℃; for 16.5h; pH=7; Reagent/catalyst; Enzymatic reaction; | 75.2% |
With cytochrome P450 2D6 expressed in human lymphoblast cells In phosphate buffer at 37℃; pH=7.4; Enzyme kinetics; | |
With yeast expressing CYP2D6 microsomes In phosphate buffer at 37℃; for 0.25h; pH=7.4; Enzyme kinetics; Further Variations:; Reagents; |
vinyl magnesium bromide
dextromethorphan
11-allyl-3-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With 1,4-diaza-bicyclo[2.2.2]octane; tri(4-tolyl)aminium hexafluorophosphate In acetonitrile at -5℃; for 0.0833333h; Inert atmosphere; Stage #2: vinyl magnesium bromide In tetrahydrofuran; acetonitrile at 0℃; for 0.0833333h; Inert atmosphere; regioselective reaction; | 75% |
(trimethylsilyl)methylmagnesium chloride
dextromethorphan
Conditions | Yield |
---|---|
With nickel diacetate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In tetrahydrofuran; toluene at 80℃; for 18h; Inert atmosphere; Sealed tube; | 74% |
cyclopropylmagnesium bromide
dextromethorphan
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With 1,4-diaza-bicyclo[2.2.2]octane; tri(4-tolyl)aminium hexafluorophosphate In acetonitrile at -5℃; for 0.0833333h; Inert atmosphere; Stage #2: cyclopropylmagnesium bromide In 2-methyltetrahydrofuran; acetonitrile at 0℃; for 0.0833333h; Inert atmosphere; regioselective reaction; | 74% |
Conditions | Yield |
---|---|
With nickel diacetate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In tetrahydrofuran; toluene at 100℃; for 18h; Inert atmosphere; Sealed tube; | 72% |
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With 1,4-diaza-bicyclo[2.2.2]octane; tri(4-tolyl)aminium hexafluorophosphate In acetonitrile at -5℃; for 0.0833333h; Inert atmosphere; Stage #2: allyl iodid With indium In N,N-dimethyl-formamide; acetonitrile at 0℃; for 0.0833333h; Inert atmosphere; regioselective reaction; | 71% |
Conditions | Yield |
---|---|
Stage #1: allyl bromide; dextromethorphan Stage #2: Alkaline hydrolysis; | 67% |
dextromethorphan
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With sulfuric acid; hydroxylamine hydrochloride In acetonitrile at 25℃; for 0.166667h; Stage #2: With hydrogenchloride; titanium(III) chloride In water; acetonitrile at 25℃; Inert atmosphere; Sealed tube; | 65% |
benzyl (2S,4S)-2-(tert-butyl)-4-isobutyl-5-oxooxazolidine-3-carboxylate
dextromethorphan
Conditions | Yield |
---|---|
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In acetonitrile at 23℃; for 12h; Irradiation; chemoselective reaction; | 64% |
neopentylmagnesium bromide
dextromethorphan
Conditions | Yield |
---|---|
With nickel diacetate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In tetrahydrofuran; toluene at 100℃; for 18h; Inert atmosphere; Sealed tube; | 60% |
Conditions | Yield |
---|---|
Stage #1: 2-Bromoethyl methyl ether; dextromethorphan Stage #2: Alkaline hydrolysis; | 59% |
dextromethorphan
Conditions | Yield |
---|---|
With N,N'-Dimethylurea; tris(pyrrolidino)phosphine oxide; lithium bromide In tetrahydrofuran at 20℃; Electrochemical reaction; | 59% |
4-penten-1-ylmagnesium bromide
dextromethorphan
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With 1,4-diaza-bicyclo[2.2.2]octane; tri(4-tolyl)aminium hexafluorophosphate In acetonitrile at -5℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-penten-1-ylmagnesium bromide In tetrahydrofuran; acetonitrile at 0℃; for 0.0833333h; Inert atmosphere; regioselective reaction; | 57% |
tris-iso-propylsilyl acetylene
dextromethorphan
Conditions | Yield |
---|---|
Stage #1: tris-iso-propylsilyl acetylene With ethylmagnesium bromide In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Glovebox; Stage #2: dextromethorphan With bis(1,5-cyclooctadiene)nickel (0); 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In 1,4-dioxane at 120℃; for 18h; Inert atmosphere; Sealed tube; | 52% |
Conditions | Yield |
---|---|
Stage #1: dextromethorphan With 1,4-diaza-bicyclo[2.2.2]octane; tri(4-tolyl)aminium hexafluorophosphate In acetonitrile at -5℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-but-1-enylmagnesium bromide In tetrahydrofuran; acetonitrile at 0℃; for 0.0833333h; Inert atmosphere; regioselective reaction; | 48% |
This chemical is called Dextromethorphan, and its systematic name is 9-alpha,13-alpha,14-alpha-Morphinan, 3-methoxy-17-methyl-. With the molecular formula of C18H25NO, its classification codes are Antitussive; Antitussive agents; Central Nervous System Agents; Drug / Therapeutic Agent; Excitatory Amino Acid Agents; Excitatory amino acid antagonists; Human Data; Neurotransmitter Agents; Respiratory System Agents. The CAS registry number of this chemical is 125-71-3. Additionally, its product categories are Respiratory Drugs; Medical and Biological Chemical; API. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity
Other characteristics of the Dextromethorphan can be summarised as followings: (1)ACD/LogP: 4.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.12; (4)ACD/LogD (pH 7.4): 2.39; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 14.9; (7)ACD/KOC (pH 5.5): 4.22; (8)ACD/KOC (pH 7.4): 78.03; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 12.47 Å2; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 81.76 cm3; (15)Molar Volume: 243.8 cm3; (16)Polarizability: 32.41×10-24cm3; (17)Surface Tension: 44.9 dyne/cm; (18)Density: 1.11 g/cm3; (19)Flash Point: 116.2 °C; (20)Enthalpy of Vaporization: 64.5 kJ/mol; (21)Boiling Point: 394.9 °C at 760 mmHg; (22)Vapour Pressure: 1.92E-06 mmHg at 25°C.
Uses of this chemical: The Dextromethorphan could be used to produce the ent-(17X)-3-methoxy-17-methyl-morphinane-17-oxide. This reaction needs the reagents of methanol, water and hydrogen peroxide.
You can still convert the following datas into molecular structure:
1.SMILES: O(c1ccc3c(c1)[C@@]24[C@@H]([C@H](N(CC2)C)C3)CCCC4)C
2.InChI: InChI=1/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1
3.InChIKey: MKXZASYAUGDDCJ-NJAFHUGGBD
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | oral | 16mg/kg (16mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ATAXIA | Pediatric Emergency Care. Vol. 7, Pg. 163, 1991. |
child | TDLo | oral | 38mg/kg (38mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Pediatric Emergency Care. Vol. 13, Pg. 214, 1997. |
dog | LDLo | intravenous | 22mg/kg (22mg/kg) | Chemical and Pharmaceutical Bulletin. Vol. 7, Pg. 372, 1959. | |
mouse | LD50 | oral | 210mg/kg (210mg/kg) | Journal of Pharmaceutical Sciences. Vol. 60, Pg. 1523, 1971. | |
mouse | LD50 | subcutaneous | 112mg/kg (112mg/kg) | Chemical and Pharmaceutical Bulletin. Vol. 7, Pg. 372, 1959. | |
rat | LD50 | intravenous | 16286ug/kg (16.286mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 1188, 1995. |
rat | LD50 | oral | 116mg/kg (116mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 1188, 1995. |
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View