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Dextromethorphan

CAS No.
125-71-3
Chemical Name:
Dextromethorphan
Synonyms
DEX;dextrophan;DextroMethorphan Base;Methorphan;Dextrometorphan;Dextromethorfan;Nodex;C06947;ba2666;Ba 2666
CBNumber:
CB1699713
Molecular Formula:
C18H25NO
Molecular Weight:
271.4
MDL Number:
MFCD00866833
MOL File:
125-71-3.mol

Dextromethorphan Properties

Melting point 80 °C
Boiling point 414.48°C (rough estimate)
Density 1.0115 (rough estimate)
refractive index 1.5740 (estimate)
Flash point 9℃
storage temp. -20°C
pka pKa 8.3 (Uncertain)
Water Solubility 12mg/L(temperature not stated)
InChIKey MKXZASYAUGDDCJ-CGTJXYLNSA-N
CAS DataBase Reference 125-71-3(CAS DataBase Reference)
FDA 21 CFR 341.14
FDA UNII 7355X3ROTS
ATC code N07XX59,R05DA09
EPA Substance Registry System Morphinan, 3-methoxy-17-methyl-, (9?,13?,14?)- (125-71-3)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS06,GHS08
Signal word  Danger
Hazard statements  H225-H301+H311+H331-H370-H301-H336
Precautionary statements  P210-P260-P280-P301+P310-P311
Hazard Codes  F,T
Risk Statements  11-23/24/25-39/23/24/25
Safety Statements  16-36/37-45
RIDADR  3249
WGK Germany  1
RTECS  QD0194000
HazardClass  6.1(b)
PackingGroup  III
HS Code  2933492250
Toxicity LD50 oral in rat: 116mg/kg

Dextromethorphan price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D-013 Dextromethorphan solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 125-71-3 1mL $23.8 2022-05-15 Buy
Sigma-Aldrich 1180503 Dextromethorphan 125-71-3 2g $1220 2022-05-15 Buy
Cayman Chemical ISO60141 Dextromethorphan (CRM) 125-71-3 1mg $18 2022-04-27 Buy
Sigma-Aldrich 1180503 Dextromethorphan United States Pharmacopeia (USP) Reference Standard 125-71-3 500mg $400 2022-05-15 Buy
Usbiological D3221-97G Dextromethorphan 125-71-3 500ul $811 2021-12-16 Buy
Product number Packaging Price Buy
D-013 1mL $23.8 Buy
1180503 2g $1220 Buy
ISO60141 1mg $18 Buy
1180503 500mg $400 Buy
D3221-97G 500ul $811 Buy

Dextromethorphan Chemical Properties,Uses,Production

Description

Dextromethorphan is an over-the-counter drug that is sold alone and in combination with other products as a cough suppressant for children and adults. We have previously recommended dextromethorphan as a safe and effective cough suppressant for both children and adults. However, the weight of the evidence now suggests that dextromethorphan is no more effective than an inactive placebo syrup in suppressing a nighttime cough in children. It is the disomer of the potent opiate analgesic 3-methoxyN-methylmorphine (levorphanol). Although dextromethorphan is structurally related to opioids, it is devoid of analgesic or sedative effects at therapeutic doses. Dextromethorphan is metabolized by CYP2D6 to a more potent metabolite, dextrorphan. Dextrorphan is a stronger noncompetitive antagonist than dextromethorphan for the N-methyl-D-aspartate (NMDA) glutamate receptor.These properties promote its use in treatment of neuropathic and postoperative pain management.

Uses

Dextromethorphan is used therapeutically as an over-thecounter cough suppressant and antitussive. It is also commonly abused particularly by adolescents because of its relative ease of availability.

Indications

Dextromethorphan is used in treating nonproductive cough. It is available widely in a variety of nonprescription forms, such as capsules, lozenges, syrups, extended-release oral suspension, and chewable tablets. This drug possesses a pronounced anticough effect and minimal action on the CNS. It is not addictive.

Definition

ChEBI: An organic heterotetracyclic compound that is morphinan substituted by a methoxy group at position 3 and a methyl group at position 7. It is used as an antitussive drug for suppressing cough.

brand name

Benylin DM (Parke-Davis); Dextromethorphan Hydrobromide OROS Tablets (Ciba-Geigy); Drixoral Cough (Schering-Plough HealthCare); PediaCare 1 (McNeil Consumer); Romilar (Hoffmann-LaRoche-International); St. Joseph Cough Syrup (Schering-Plough HealthCare);Agrippol;Dextophan;Dextrophen.

Biological Functions

Dextromethorphan hydrobromide is the D-isomer of levorphanol. It lacks CNS activity but acts at the cough center in the medulla to produce an antitussive effect. It is half as potent as codeine as an antitussive. Anecdotal reports of abuse exist, but studies of abuse potential are lacking. It has few side effects but does potentiate the activity of monoamine oxidase inhibitors, leading to hypotension and infrequently coma. Dextromethorphan is often combined in lozenges with the local anesthetic benzocaine, which blocks pain from throat irritation due to coughing.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 1769, 1965 DOI: 10.1021/jo01017a014

General Description

Dextromethorphan is the dextrorotatory form of levorphanolwith a methoxy group on the 3-position. It is availablein more than 140 over-the-counter (OTC) cough and coldformulations. Evidence-based reviews have been unable toconclude that it is more effective than placebo in reducingcough. Like (+) and (-) levorphanol, (+) dextromethorphanis a potent NMDA antagonist and, in higher than recommendeddoses, has the potential for causing dissociativeanesthetic effects similar to ketamine or phencyclidine (PCP).The OTC status and availability of pure dextromethorphanpowder online has contributed greatly to its abuse in recentyears. DAWN reports that in 2004, there were approximately12,500 emergency room visits involving dextromethorphanwith 44% of those involving abuse of the drug. The 2006National Survey on Drug Abuse report shows that nearly 1million persons aged 12 to 25 years (1.7%) misused OTCcough and cold medications in the past year.
Dextromethorphan’s ability to antagonize the NMDA receptorhas led to its use to treat phantom pain, diabetic neuropathy,and postoperative acute pain.

Pharmacokinetics

Dextromethorphan is absorbed rapidly from the GI tract, with antitussive activity occurring within 15 to 30 minutes. It undergoes extensive hepatic metabolism. Excretion is mainly renal, with some drug eliminated unchanged but most eliminated as metabolites. Dextromethorphan is related chemically to the opiate agonists and can suppress coughing as effectively as narcotics. Cough suppression occurs by several mechanisms, but mainly the drug directly affects the cough center in the medulla. Therapeutic doses do not affect ciliary activity.

Side effects

Although adverse effects are generally rare, dextromethorphan toxicity can occur and is characterized by nausea and vomiting, drowsiness, dizziness, irritability, and restlessness. In excessive doses, dextromethorphan poisoning may occur and induce symptoms similar to those associated with phencyclidine.

Safety

Despite the safety of dextromethorphan when used at the recommended dosage (<120 mg/day), higher doses can result in nausea, vomiting, seizure, loss of consciousness, irregular heartbeat, and death. Serotonin syndrome may develop in patients on other serotonergic drugs, due to additive inhibition of serotonin reuptake by dextromethorphan. Patients with genetic variations in CYP2D6, causing rapid metabolism of dextromethorphan, may present with greater clinical effects.

Chemical Synthesis

Dextromethorphan, (9α,13α,14α)-3-methoxy-17-methylmorphinane (23.2.1), is synthesized from ()-3-hydroxy-N-methylmorphinane by methylating the phenol hydroxyl group using phenyltrimethylammonium chloride and sodium methoxide in methanol. The resulting racemic product ()-3-methoxy-N-methylmorphinane is separated into isomers using D-tartaric acid, which produces dextromethor-phan.

Environmental Fate

Dextromethorphan is the D-isomer of the codeine analog, methorphan. Unlike the L-isomer, it has no analgesic or addictive properties and does not act through the opioid receptors. The exact mechanism for the antitussive effect by dextromethorphan remains unclear and is likely multifactorial. Dextromethorphan is known to be an N-methyl-D-aspartate (NMDA) receptor antagonist; however, dextromethorphan binding sites are not limited to the known distribution of NMDA receptors.
Dextromethorphan’s main metabolite, dextrorphan, has NMDA receptor antagonist properties similar to ketamine and phencyclidine. This NMDA receptor antagonism is believed to result in a decreased reuptake of catecholamines. Dextromethorphan also inhibits the reuptake of serotonin. These properties make dextromethorphan have a high abuse and misuse potential.
Dextromethorphan is a common ingredient in over-thecounter cough and cold preparations, and is often combined with other agents including concurrent antihistamines, decongestants, analgesics, and ethanol. Patients may exhibit toxicity due to these coingestants.

Dextromethorphan Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 129)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Lingding Biological Technology Co., Ltd
+86-19933155420 +86-19933155420 sales1@hbldbiotech.com China 940 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 22021 55
Shanxi Naipu Import and Export Co.,Ltd
+86-13734021967 +8613734021967 kaia@neputrading.com China 1011 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29960 58
Xi'an Kono chem co., Ltd.,
029-86107037 13289246953 info@konochemical.com China 2996 58
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 23034 58
Shanghai Longyu Biotechnology Co., Ltd.
+8615821988213 info@longyupharma.com China 2522 58
Chongqing Chemdad Co., Ltd
+8613650506873 sales@chemdad.com CHINA 37442 58
Shaanxi Dideu Medichem Co. Ltd
18192627656 1012@dideu.com China 3950 58
Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418671 sales@tnjchem.com CHINA 34618 58

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View Lastest Price from Dextromethorphan manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2022-04-21 dextromethorphan
125-71-3
US $100.00 / bag 1bag 99 500 Shanxi Naipu Import and Export Co.,Ltd
2022-03-23 Dextromethorphan
125-71-3
US $10.00 / g 100g 99% 10tons Henan Guange Biotechnology Co. LTD
2022-03-17 DEXTROMETHORPHAN
125-71-3
US $270.00 / kg 1kg 99 10000kg/month Hebei Yime New Material Technology Co., Ltd.
  • dextromethorphan
    125-71-3
  • US $100.00 / bag
  • 99
  • Shanxi Naipu Import and Export Co.,Ltd
  • DEXTROMETHORPHAN
    125-71-3
  • US $270.00 / kg
  • 99
  • Hebei Yime New Material Technology Co., Ltd.
D-methorphan Morphinan, 3-methoxy-17-methyl-, (9alpha,13alpha,14alpha)- Racemethorphan [as d-form] [9α,13α,14α,(+)]-3-Methoxy-17-methylmorphinan C06947 (+)-3-methoxy-N-methylmorphinan (+)-cis-1,3,4,9,10,10a-hexahydro-6-methoxy-11-methyl-2H-10,4a-iminoethanophenanthrene Benylin DM D-1,2,3,9,10,10a-Hexahydro-6-methoxy-11-methyl-4H-10,4a-iminoethanophenanthrene D-3-Methoxy-N-methylmorphinan DXM Free Base Romilar CF DEXTROMETHORPHANE HBR Dextromethorphan Bromhydrate Dextromethorphane DEXYROMETHORPHAN DEXTROMETHORPHAN,1.0MG/MLINMETHANOL DEXTROMETHORPHAN,USP 9α,13α,14α-Morphinan, 3-methoxy-17-methyl- (8CI) Morphinan, 3-methoxy-17-methyl-, (9α,13α,14α)- Nodex Dextromethorphan, >=99% 9-alpha,-14-alpha-3-Methoxy-17-methylmorphinan DextroMethorphan - CHECK BUYER INFO Dextromethorphan solution Dextromethorphan (2 g) Dextromethorphan, 1.0 mg/mL DEXTROMETHORPHAN 13-alpha,14-alpha-morphinan,3-methoxy-17-methyl-9-alph 13alpha,14alpha-morphinan,3-methoxy-17-methyl-9alph 3-methoxy-17-methyl-,(9-alpha,13-alpha,14-alpha)-morphina 3-Methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan 3-Methoxy-17-methyl-9alpha,13alpha-morphinan 3-Methoxy-17-methylmorphinan 9alpha,13alpha,14alpha-Morphinan, 3-methoxy-17-methyl- Ba 2666 ba2666 delta-Methorphan Dextromethaphan Dextromethorphan (CRM) dxm hbr Pure Dxm Powder DEXTROMETHORPHAN USP/EP/BP Dextromethorphan D3 HCl Dextromethorphan (1180503) 4-Anthraquinone Methorphan Dextrometorphan dextrophan DEX DextroMethorphan Base Dextromethorfan Morphinan,3-methoxy-17-methyl-, (9α,13α,14α)- 125-71-3 C18H25NO 125-71-3