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125-71-3

Basic Information
CAS No.: 125-71-3
Name: DEXTROMETHORPHAN
Article Data: 26
Molecular Structure:
Molecular Structure of 125-71-3 (DEXTROMETHORPHAN)
Formula: C18H25NO
Molecular Weight: 271.403
Synonyms: 9α,13α,14α-Morphinan, 3-methoxy-17-methyl- (8CI);(+)-3-Methoxy-17-methylmorphinan;Ba 2666;Nodex;d-Methorphan;
EINECS: 204-752-2
Density: 1.11 g/cm3
Melting Point: 80 °C
Boiling Point: 394.9 °C at 760 mmHg
Flash Point: 116.2 °C
Solubility: 12mg/L(temperature not stated)
Hazard Symbols: F,T
Risk Codes: 11-23/24/25-39/23/24/25
Safety: 16-36/37-45
Transport Information: UN 3249
PSA: 12.47000
LogP: 3.32130
Synthetic route

dextromethorphan hydrobromide

125-71-3

dextromethorphan

Conditions
ConditionsYield
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
6700-34-1

dextromethorphan hydrobromide, monohydrate

125-71-3

dextromethorphan

Conditions
ConditionsYield
With sodium hydroxide In chloroform; water for 0.5h;97.98%
113951-04-5

dextromethorphan N-oxide hydrochloride

B

125-71-3

dextromethorphan

Conditions
ConditionsYield
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%
67596-84-3

(+)-2-methyl-1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8-hexahydroisoquinoline

125-71-3

dextromethorphan

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃; for 2h; Reagent/catalyst;91%
125-70-2, 125-71-3, 510-53-2, 3561-92-0

rac-3-methoxy-17-methyl-morphinane

125-71-3

dextromethorphan

Conditions
ConditionsYield
Gewinnung mit Hilfe von Lg-Weinsaeure;
Gewinnung mit Hilfe von Lg-Weinsaeure;
57969-05-8

(9α,13α,14α)-3-methoxy-17-methylmorphinan-10-one

A

125-71-3

dextromethorphan

B

133443-97-7

ent-3-methoxy-17-methyl-morphinan-10β-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
28973-48-0

(+)-3-methoxy-N-formylmorphinan

125-71-3

dextromethorphan

1899-02-1

trimethylphenylammonium hydroxide

ent-17-methyl-morphinan-3-ol

ent-17-methyl-morphinan-3-ol

125-71-3

dextromethorphan

Conditions
ConditionsYield
With methanol; toluene
With methanol; toluene
104-01-8

4-Methoxyphenylacetic acid

125-71-3

dextromethorphan

Conditions
ConditionsYield
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
51072-35-6

1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline

125-71-3

dextromethorphan

Conditions
ConditionsYield
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
Downstream Products
1531-23-3
28973-48-0
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History

1、Dextromethorphan was first patented under U.S. Patent 2,676,177.
2、The U.S. Food and Drug Administration (FDA) approved dextromethorphan for over-the-counter sale as a cough suppressant in 1958.
3、During the 1960s and 1970s, dextromethorphan became available in an over-the-counter tablet form by the brand name Romilar.
4、In 1973, Romilar was taken off the shelves after a burst in sales due to frequent abuse, and was replaced by cough syrup in an attempt to cut down on abuse.
5、More recently (the early 1990s), gel capsule forms began reappearing in the form of Drixoral Cough Liquid Caps and later Robitussin CoughGels as well as several generic forms of that preparation.

Specification

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.

The Dextromethorphan could be used to produce the ent-(17X)-3-methoxy-17-methyl-morphinane-17-oxide

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.