Buy Butorphanol Cas-42408-82-2

Buy Butorphanol Cas-42408-82-2

Buy Butorphanol Cas-42408-82-2

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Buy Butorphanol Cas-42408-82-2

Buy Butorphanol Cas-42408-82-2

Butorphanol is a morphinan-type synthetic agonist–antagonist opioid analgesic developed by Bristol-Myers. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available as the tartrate salt in injectable, tablet, and intranasal spray formulations. The tablet form is only used in dogs, cats and horses due to low bioavailability in humans.

It was patented in 1971 and approved for medical use in 1979.

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Butorphanol, a semi-synthetic opioid agonist-antagonist analgesic, is structurally a morphinan and shares the same cyclobutyl methyl group on the nitrogen as nalbuphine. It acts as an agonist at the κ-receptor and as a partial agonist and antagonist at the μ-receptor. Butorphanol exhibits high affinity for the κ-receptors, which is believed to contribute to its analgesic properties and central nervous system adverse effects such as hallucinations, psychosis, and paranoid reactions. It is used in its (S,S)-tartaric acid salt form for relief of moderate to severe pain.
Brand name: Stadol (Bristol-Myers Squibb).

42408-82-2

  • 42408-82-2 Structure

  • Basic information

    1. Product Name: BUTORPHANOL
    2. Synonyms: (-)-17-(CyclobutylMethyl)-3,14β- dihydroxyMorphinan;17-(cyclobutylmethyl)-morphinan-14-diol;17-(cyclobutylmethyl)morphinan-3,14-diol;BUTORPHANOL;(-)-17-(Cyclobutylmethyl)-3,14b-dihydroxymorphinan;BC 2627, (-)-;l-3,14-Dihydroxy-N-(cyclobutylmethyl)morphinan;l-BC 2627
    3. CAS NO:42408-82-2
    4. Molecular Formula: C21H29NO2
    5. Molecular Weight: 327.46
    6. EINECS: 255-808-8
    7. Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 42408-82-2.mol

  • Chemical Properties

    1. Melting Point: 215-217°
    2. Boiling Point: 507.3 °C at 760 mmHg
    3. Flash Point: 265.9 °C
    4. Appearance: /
    5. Density: 1.24 g/cm3
    6. Refractive Index: 1.642
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: pKa 8.6 (Uncertain)
    10. CAS DataBase Reference: BUTORPHANOL(CAS DataBase Reference)
    11. NIST Chemistry Reference: BUTORPHANOL(42408-82-2)
    12. EPA Substance Registry System: BUTORPHANOL(42408-82-2)

  • 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: 42408-82-2(Hazardous Substances Data)

42408-82-2 Suppliers

This product is a nationally controlled contraband or patented product, and the Lookchem platform doesn’t provide relevant sales information.

42408-82-2 Usage

Uses

Used in Pharmaceutical Industry:
Butorphanol is used as an analgesic for the relief of moderate to severe pain. Its high affinity for κ-receptors is responsible for its analgesic properties, while its partial agonist and antagonist activity at the μ-receptor helps to reduce the risk of dependence and withdrawal symptoms in patients maintained on high-potency μ-agonists such as morphine.
Used in Antitussive Applications:
Butorphanol is used as an antitussive to suppress coughing by acting on the cough center in the brain. Its agonist-antagonist properties allow it to effectively reduce cough reflex without causing significant respiratory depression.
Used in Controlled Substances:
Butorphanol is classified as a controlled substance due to its potential for abuse and dependence. Its use is regulated to ensure that it is prescribed and used appropriately for medical purposes, minimizing the risk of misuse and addiction.

Originator

Stadol,Bristol-Myers,US,1978

Manufacturing Process

A mixture of 1.0 g (2.58 mmols) of N-cyclobutylmethyl-14-hydroxy-9- methoxymorphinan and 10 ml of 48% HBr was refluxed, under a nitrogen atmosphere, during five minutes. After cooling, the reaction mixture was diluted with water and made basic with aqueous ammonium hydroxide. The aquous basic mixture was extracted with chloroform and the combined chloroform extracts were dried over anhyrous sodium sulfate. After evaporation of the solvent, the residual oil (730 mg) was taken up in dry ether and the resulting solution filtered through celite-charcoal. The filtrate was treated with a saturated solution of hydrogen chloride in dry ether. The hydrochloride salt thus obtained was collected by filtration and recrystallized from a methanol-acetone mixture to yield 565 mg (56.5%)of Butorphanol hydrochloride crystals melting at 272°-274°C (decomposition).

Therapeutic Function

Analgesic, Antitussive

Biological Functions

Butorphanol (Stadol) is chemically related to levorphanol but pharmacologically similar in action to pentazocine. As an opioid antagonist it is nearly 30 times as potent as pentazocine and has one-fortieth the potency of naloxone. It is a potent opioid analgesic indicated for the relief of moderate to severe pain. Its potency is 7 times that of morphine and 20 times that of pentazocine as an analgesic. Its onset of action is similar to that of morphine.The side effects and signs of toxicity are similar to those produced by pentazocine. It produces excitatory effects and sedation and precipitates withdrawal in opioid-dependent patients. Although generally administered parenterally because of its low bioavailability following oral administration, it is also unique in that a nasal spray formulation is available.The nasal spray is indicated for the relief of postoperative pain and migraine headache. The low molecular weight of butorphanol, its high lipophilicity, and its lack of vasoconstrictor effects make it particularly suitable for nasal administration.Nasal administration of butorphanol decreases the onset of action to 15 minutes and decreases the firstpass effect of the drug, which increases bioavailability. Generally the patient sprays a set dose of 1 mg per hour for 2 hours. The duration of action is 4 to 5 hours. The convenience of such administration is a major advantage to patients requiring repeat dosing. The abuse potential following such administration has not been extensively studied, although it is thought to be small. Butorphanol is not a federally controlled (“scheduled”) drug, so physicians are not required to obtain the licenses and security safeguards required for other opioid analgesics. Adverse effects, contraindications, and drug interactions are similar to those for pentazocine and morphine.

Check Digit Verification of cas no

The CAS Registry Mumber 42408-82-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,4,0 and 8 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 42408-82:
(7*4)+(6*2)+(5*4)+(4*0)+(3*8)+(2*8)+(1*2)=102
102 % 10 = 2
So 42408-82-2 is a valid CAS Registry Number.

InChI:InChI=1/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1

42408-82-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name butorphanol

1.2 Other means of identification

Product number –
Other names BUTORPHANOL

1.3 Recommended use of the chemical and restrictions on use

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

1.4 Supplier’s details

1.5 Emergency phone number

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

More Details:42408-82-2 SDS

42408-82-2Upstream product

42408-82-2Relevant academic research and scientific papers

AN IMPROVED PROCESS FOR THE PREPARATION OF BUTORPHANOL TARTRATE

–

Page/Page column 25, (2017/11/03)

The present invention relates to an improved process for the preparation of Butorphanol tartrate of formula (I),

Combination of selected opioids with muscarine antagonists for treating urinary incontinence

–

, (2008/06/13)

Active compound combinations of compounds of group A, particularly opioids, and compounds of group B, particularly anti-muscarine agents and other substances suitable for treatment of an increased urge to urinate or urinary incontinence. Related pharmaceutical formulations and methods of treatment of an increased urge to urinate or urinary incontinence are also provided.

Process for the preparation of 14-hydroxymorphinan derivatives

–

, (2008/06/13)

N-substituted-14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound 3,14-dihydroxy-N-cyclobutylmethylmorphinan has been found to possess potent agonist/antagonist activity. A new and novel total synthesis for the preparation of these compounds is described herein.

Process for the preparation of 14-hydroxymorphinans

–

, (2008/06/13)

N-substituted-14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound 3,14-dihydroxy-N-cyclopropylmethylmorphinan has been found to possess potent agonist-antagonist activity. A new and more efficient total synthesis for the preparation of these compounds is described herein, which improvement comprises using a Schiff base of 4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene to produce 3-methoxy-9-bromo-norhasubanan hydrobromide in substantially improved yields through the intermediate of the formula SPC1

Oxilorphan and butorphanol. Potent narcotic antagonists and nonaddicting analgesics in the 3,14 dihydroxymorphinan series. Part V

Monkovic,Wong,Pircio,et al.

, p. 3094 – 3102 (2007/10/10)

A series of 3,14 dihydroxymorphinans 8 was synthesized via a method of (a) acylation of 3 methoxy Δ84 morphinan 4a (b) stereospecific epoxidation of the resultant amides to β epoxides 5 (c) simultaneous reduction of amide and epoxide functions and (d) demethylation of the resultant 3 methoxy 14 hydroxymorphinans 7. Alternatively deblocking of the amine function in 5b by hydrolysis followed by reduction of the resultant amino epoxide 5e afforded 14 hydroxy 3 methoxymorphinan 7e, which is readily alkylated and demethylated to give various 8. On a basis of interesting pharmacological profiles compounds l 8c (oxilorphan) and l 8d (butorphanol) were selected for clinical studies.

Medical uses

The most common indication for butorphanol is management of migraine using the intranasal spray formulation. It may also be used parenterally for management of moderate-to-severe pain, as a supplement for balanced general anesthesia, and management of pain during labor. Butorphanol is also quite effective at reducing post-operative shivering (owing to its kappa agonist activity). Butorphanol is more effective in reducing pain in women than in men.[6]

Pharmacology

Butorphanol exhibits partial agonist and antagonist activity at the μ-opioid receptor, as well as partial agonist activity at the κ-opioid receptor (Ki = 2.5 nM; EC50 = 57 nM; Emax = 57%).[6][7] Stimulation of these receptors on central nervous system neurons causes an intracellular inhibition of adenylate cyclase, closing of influx membrane calcium channels, and opening of membrane potassium channels. This leads to hyperpolarization of the cell membrane potential and suppression of action potential transmission of ascending pain pathways. Because of its κ-agonist activity, at analgesic doses butorphanol increases pulmonary arterial pressure and cardiac work. Additionally, κ-agonism can cause dysphoria at therapeutic or supratherapeutic doses; this gives butorphanol a lower potential for abuse than other opioid drugs.[8]

Society and culture

Name

Within the INN, USAN, BAN, and AAN naming systems this drug is known as butorphanol, while within JAN it is named torbugesic.[2][3][4] As the tartrate salt, butorphanol is known as butorphanol tartrate (USAN, BAN).[2][3][4]

Butorphanol is listed under the Single Convention on Narcotic Drugs 1961 and in the United States is a Schedule IV controlled substance with a DEA ACSCN of 9720.[9] The free base conversion ratio of the hydrochloride is 0.69.[10] Butorphanol was originally a Schedule II controlled substance and was later decontrolled at one point.

 

Description

Butorphanol is levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the N-methyl group is substituted by cyclopropyl. A semi-synthetic opioid agonist-antagonist analgesic, it is used as its (S,S)-tartaric acid salt for relief or moderate to severe pain. It has a role as an opioid analgesic, a mu-opioid receptor agonist, a kappa-opioid receptor agonist and an antitussive.
Butorphanol is a DEA Schedule IV controlled substance. Substances in the DEA Schedule IV have a low potential for abuse relative to substances in Schedule III. It is a Other substances substance.
A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain.
Butorphanol is an Opioid Agonist/Antagonist. The mechanism of action of butorphanol is as a Competitive Opioid Antagonist, and Partial Opioid Agonist.
Butorphanol is a synthetic opioid which is used as a nasal spray for treatment of migraine headaches and parenterally as a narcotic analgesic for moderate-to-severe pain or as an adjunct to general anesthesia. Butorphanol has not been linked to serum enzyme elevations during therapy or to clinically apparent liver injury.
See also: Butorphanol Tartrate (has salt form).

Source and Classification

Butorphanol is classified as an opioid analgesic and is part of the morphinan family of compounds. Its chemical formula is C21H29NO2, with a molecular weight of approximately 327.46 g/mol. The compound is often referred to by its IUPAC name: (−)-17-(cyclobutylmethyl)morphinan-3,14-diol. Butorphanol was introduced as a parenteral formulation in 1978 and has since been available in various forms, including injectable and transnasal formulations .

Synthesis Analysis

The synthesis of butorphanol typically involves several steps, utilizing various starting materials and intermediates. One notable method includes the use of racemic 1-p-methoxybenzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline as a precursor. This process involves six key steps: acylation, epoxidation, hydrolysis, reduction, cyclization, and demethylation .

Key Steps in Synthesis

  1. Acylation: Introduction of acyl groups to the precursor.
  2. Epoxidation: Formation of an epoxide ring.
  3. Hydrolysis: Conversion of epoxides to diols.
  4. Reduction: Reduction reactions to form alcohols.
  5. Cyclization: Formation of cyclic structures.
  6. Demethylation: Removal of methyl groups to yield the final product.

Molecular Structure Analysis

The molecular structure of butorphanol features a morphinan backbone with hydroxyl groups at positions 3 and 14. The presence of a cyclobutylmethyl group at position 17 contributes to its unique pharmacological profile.

Structural Characteristics

  • Molecular Formula: C21H29NO2
  • Hydroxyl Groups: Two hydroxyl groups enhance its solubility and interaction with opioid receptors.
  • Chiral Centers: Butorphanol has chiral centers that contribute to its stereospecific activity.

The three-dimensional arrangement of atoms in butorphanol allows it to fit into the binding sites of opioid receptors effectively, influencing its potency and efficacy as an analgesic.

Chemical Reactions Analysis

Butorphanol undergoes various chemical reactions during its metabolism and synthesis. Notably:

  • Hydroxylation: Conversion into metabolites such as trans-hydroxybutorphanol.
  • Glucuronidation: Formation of glucuronide conjugates for excretion .
  • Dealkylation: Removal of alkyl groups during synthesis can lead to different derivatives with altered pharmacological properties.

These reactions are crucial for understanding both the synthesis pathways and the metabolic fate of butorphanol in biological systems.

Mechanism of Action

Butorphanol acts primarily as a mixed agonist-antagonist at opioid receptors, specifically targeting the mu (μ) and kappa (κ) receptors. Its mechanism involves:

  • Agonistic Activity: Binding to mu receptors to elicit analgesic effects.
  • Antagonistic Activity: Blocking kappa receptors which may help mitigate some side effects associated with pure agonists.

This dual action allows butorphanol to provide effective pain relief while potentially reducing the risk of dependence compared to traditional opioids .

Physical and Chemical Properties Analysis

Butorphanol exhibits several notable physical and chemical properties:

  • Appearance: Typically a white crystalline solid.
  • Solubility: Soluble in organic solvents such as ethanol and dichloromethane; limited solubility in water due to hydrophobic characteristics.
  • Melting Point: Approximately 180 °C.
  • pKa Values: Reflecting its acidic hydroxyl groups which influence its ionization at physiological pH.

These properties are significant for formulation development and influence how butorphanol is administered clinically.

Applications

Butorphanol is widely used in clinical settings for:

  • Pain Management: Effective for moderate to severe pain relief post-surgery or during labor.
  • Anesthesia Adjunct: Used alongside anesthetic agents for enhanced analgesia during surgical procedures.
  • Transnasal Formulation: Offers a non-invasive route for pain management that bypasses gastrointestinal metabolism .

In addition to its therapeutic uses, butorphanol serves as a valuable research tool in pharmacology for studying opioid receptor interactions.

Properties

CAS Number

42408-82-2

Product Name

Butorphanol

IUPAC Name

(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol

Molecular Formula

C21H29NO2

Molecular Weight

327.5 g/mol

InChI

InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1

InChI Key

IFKLAQQSCNILHL-QHAWAJNXSA-N

SMILES

C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)O

Solubility

Moderate

Synonyms

17-(Cyclobutylmethyl)morphinan-3,14-diol
Apo-Butorphanol
BC 2627
BC-2627
BC2627
Beforal
Butorphanol
Butorphanol Tartrate
Dolorex
Moradol
Stadol
Stadol NS
Torbugesic

Canonical SMILES

C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)O

Isomeric SMILES

C1CC[C@]2([C@H]3CC4=C([C@]2(C1)CCN3CC5CCC5)C=C(C=C4)O)O

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    • Mol.Wt: 327.5

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