Dextrallorphan is primarily derived from dextromethorphan, a common cough suppressant found in many over-the-counter medications. Dextromethorphan itself is synthesized through several chemical pathways, including the reaction of morphinan derivatives with various alkylating agents. The transformation into dextrallorphan involves specific modifications to the molecular structure of dextromethorphan.

Dextrallorphan is classified as a sigma receptor ligand, specifically targeting sigma-1 and sigma-2 receptors. Its classification underlines its significance in research related to neurological disorders and potential therapeutic applications.

Methods

The synthesis of dextrallorphan can be achieved through various methods, with the most common involving the modification of dextromethorphan. Traditional synthetic pathways include:

• Alkylation Reactions: Utilizing alkyl halides to introduce functional groups.
• Reductive Amination: Converting ketones or aldehydes into amines, which can then be further modified.

Technical Details

One notable method for synthesizing dextrallorphan involves the use of deuterated reagents to enhance the specificity and yield of the product. For instance, the von Braun reaction has been documented but is often avoided due to toxicity concerns associated with cyanogen halides. Instead, safer alternatives such as using hydrobromic acid under controlled conditions have been emphasized in recent studies, achieving high purity levels (over 99% as verified by techniques like gas chromatography-mass spectrometry)   .

Structure

Dextrallorphan has a complex molecular structure characterized by its chiral centers. Its molecular formula is C18H25NO, and it features a morphinan backbone similar to that of dextromethorphan but with specific modifications that enhance its receptor binding properties.

Data

The molecular weight of dextrallorphan is approximately 275.4 g/mol. The compound exhibits distinct NMR (Nuclear Magnetic Resonance) signals that confirm its structural integrity and purity during synthesis   .

Reactions

Dextrallorphan participates in several chemical reactions typical for amine derivatives, including:

• Acid-Base Reactions: Exhibiting basic properties due to the amine group.
• Nucleophilic Substitution: Reacting with electrophiles to form new bonds.

Technical Details

The interaction of dextrallorphan with sigma receptors can also be considered a significant reaction pathway. Binding assays have shown that dextrallorphan effectively masks sigma-1 receptors when assessing sigma-2 receptor activity, highlighting its role in pharmacological research  .

Process

Dextrallorphan functions primarily as a sigma receptor modulator. Upon binding to sigma receptors, it alters neurotransmitter release and neuronal excitability, which can influence pain perception and mood regulation.

Data

Studies indicate that dextrallorphan’s binding affinity for sigma receptors can lead to significant biological effects, including potential neuroprotective actions and modulation of dopaminergic activity   .

Physical Properties

• Appearance: Typically exists as a white crystalline powder.
• Melting Point: The melting point ranges between 121°C and 123°C, indicating stability under standard conditions.

Chemical Properties

• Solubility: Soluble in organic solvents such as methanol and ethanol but less so in water.
• Stability: Generally stable under normal laboratory conditions but sensitive to strong acids or bases.

Relevant analyses confirm that dextrallorphan maintains high purity levels post-synthesis, ensuring reliable performance in experimental applications   .

Dextrallorphan’s primary applications lie within scientific research, particularly in pharmacology and neuroscience:

• Sigma Receptor Studies: Utilized as a tool for investigating the roles of sigma receptors in various physiological processes.
• Potential Therapeutics: Research suggests possible applications in treating neurological disorders due to its modulatory effects on neurotransmitter systems.

Molecular Structure and Stereochemical Configuration

Dextrallorphan (DXA) is a synthetic morphinan alkaloid with the systematic IUPAC name (+)-(9α,13α,14α)-17-allylmorphinan-3-ol and molecular formula C₁₉H₂₅NO (molar mass: 283.415 g/mol). Its core structure consists of a pentacyclic phenanthrene backbone with the following stereochemical features [1] [3] [7]:

• Absolute configuration: The chiral centers at C9, C13, and C14 exhibit α-orientation, conferring dextrorotatory optical activity.
• Functional groups: A phenolic hydroxyl group at C3 (critical for σ1 receptor binding) and an allyl substituent (-CH₂-CH=CH₂) at the nitrogen atom (N17).
• Stereochemical specificity: The (9α,13α,14α) enantiomer displays distinct pharmacological properties compared to its levorotatory counterpart, levallorphan, which exhibits 10,000-fold higher affinity for opioid receptors [1] [5].

Interactive Table 1: Atomic Coordinates of Dextrallorphan

Comparative Analysis with Morphinan Derivatives

Dextrallorphan’s pharmacological profile diverges significantly from structurally related morphinans due to stereoelectronic factors:

Receptor Affinity Contrasts (Ki, nM) [1] [5] [6]:

*Nicotinic acetylcholine receptor IC₅₀; NMDA affinity via MK-801 displacement

Key Structural Determinants:

• C3 Substitution: Dextrallorphan’s phenolic OH enables σ1 binding, whereas dextromethorphan’s methoxy group enhances serotonin transporter (SERT) inhibition [4] [8].
• N17 Modification: The 17-allyl group in dextrallorphan sterically hinders opioid receptor engagement, contrasting with dextrorphan’s N-methyl group, which permits weak μ-opioid binding [6].
• Stereoisomerism: Levallorphan ((−)-enantiomer) binds opioid receptors with nanomolar affinity, while dextrallorphan’s (+)-configuration shifts selectivity toward σ1/NMDA sites [5] [7].

Interactive Table 2: Functional Group Impact on Pharmacodynamics

Physicochemical Properties and Stability

Dextrallorphan’s bioactive conformation is influenced by intramolecular interactions and environmental factors:

Critical Properties:

• Ionization: Phenolic hydroxyl (pKa ≈ 10.2) confers weak acidity; tertiary amine (pKa ≈ 8.9) enables protonation at physiological pH [2] [3].
• Lipophilicity: Experimental logP ≈ 3.8 ± 0.2, indicating moderate membrane permeability. The allyl group enhances hydrophobic surface area vs. N-methyl analogs (e.g., dextrorphan logP ≈ 3.2) [2] [7].
• Solid-State Behavior: Crystalline monohydrate form is stable under ambient conditions but degrades upon prolonged UV exposure (>48 hrs). Accelerated stability studies show <5% decomposition after 24 months at –20°C [3].

Interactive Table 3: Comparative Physicochemical Profiles

Degradation Pathways:

• Oxidation: Allyl side chain forms epoxy derivatives under aerobic conditions.
• Photolysis: Ring A aromatization yields quinone-like impurities (λmax = 320 nm).
• Hydrolysis: Stable in pH 4–8 buffers; extreme alkalinity (pH >10) cleaves the C4–O5 ether linkage

Dextrallorphan

• CAS No.:

  5822-43-5

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Dextrorphan, also known as dextrallorphan, is a psychoactive drug that serves as an active metabolite of the opioid medication dextromethorphan. Classified as a dissociative drug, it can induce hallucinations and a sense of detachment from reality. It operates by blocking NMDA receptors in the brain, which are integral to pain perception and memory function. Additionally, dextrorphan is a potent sigma-1 receptor agonist, potentially contributing to its psychoactive properties. It has been the subject of research for its potential in treating neurodegenerative diseases and as a supplement to opioid therapy, while also being misused recreationally for its hallucinogenic effects.

5822-43-5

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• Basic information

  1. Product Name: dextrallorphan
  2. Synonyms: dextrallorphan;(9α,13α,14α)-17-(2-Propenyl)morphinan-3-ol
  3. CAS NO:5822-43-5
  4. Molecular Formula: C₁₉H₂₅NO
  5. Molecular Weight: 283.41
  6. EINECS: N/A
  7. Product Categories: N/A

• Chemical Properties

  1. Melting Point: N/A
  2. Boiling Point: 433.5°Cat760mmHg
  3. Flash Point: 214.2°C
  4. Appearance: /
  5. Density: 1.14g/cm³
  6. Vapor Pressure: 4.02E-08mmHg at 25°C
  7. Refractive Index: 1.614
  8. Storage Temp.: N/A
  9. Solubility: N/A
  10. CAS DataBase Reference: dextrallorphan(CAS DataBase Reference)
  11. NIST Chemistry Reference: dextrallorphan(5822-43-5)
  12. EPA Substance Registry System: dextrallorphan(5822-43-5)

• Safety Data

  1. Hazard Codes: N/A
  2. Statements: N/A
  3. Safety Statements: N/A
  4. WGK Germany:
  5. RTECS:
  6. HazardClass: N/A
  7. PackingGroup: N/A
  8. Hazardous Substances Data: 5822-43-5(Hazardous Substances Data)

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5822-43-5 Usage

Uses

Used in Neurodegenerative Disease Treatment:
Dextrorphan is used as a therapeutic agent for neurodegenerative diseases, leveraging its ability to modulate NMDA receptors and potentially offering neuroprotective benefits.
Used in Opioid Therapy:
Dextrorphan is utilized as an adjunct to opioid therapy, where it may enhance the overall analgesic effect and potentially reduce the required dosage of opioids, thereby managing pain more effectively.
Used in Recreational Settings:
Although not recommended due to health risks and legal implications, dextrorphan is abused recreationally for its hallucinogenic properties, providing a sense of detachment and altered perception of reality.
Used in Research:
Dextrorphan is employed in scientific research as a tool to study the effects and mechanisms of NMDA receptor antagonism and sigma-1 receptor activation, furthering our understanding of their roles in various neurological conditions and potential therapeutic applications.

Check Digit Verification of cas no

The CAS Registry Mumber 5822-43-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,8,2 and 2 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5822-43:
(6*5)+(5*8)+(4*2)+(3*2)+(2*4)+(1*3)=95
95 % 10 = 5
So 5822-43-5 is a valid CAS Registry Number.

InChI:InChI=1/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19-/m1/s1

5822-43-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) – Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name	Dextrallorphan

1.2 Other means of identification

Product number	–
Other names	ent-17-allyl-morphinan-3-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses	For industry use only.
Uses advised against	no data available

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1.5 Emergency phone number

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Service hours	Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

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Synonyms

(9α,13α,14α)-17-(2-Propen-1-yl)morphinan-3-ol; (9α,13α,14α)-17-(2-Propenyl)morphinan-3-ol; dextrallorphan; Morphinan-3-ol, 17-(2-propen-1

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dextrallorphan

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• Content:

  99%

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  25kg/Cardboard Drum

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Dextrallorphan, DXA,

• CAS No.:

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