561-27-3

Usage

Uses

Used in Medical Applications:
HEROIN DIACETYLMORPHINE is used as an analgesic for the treatment of acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses. Its high potency and rapid onset of action make it a potent pain reliever, although its addictive properties limit its clinical use.
Used in Illicit Drug Trade:
Unfortunately, HEROIN DIACETYLMORPHINE is also used for recreational purposes and is a common drug in the illicit drug trade. Its addictive nature and rapid onset of effects make it a popular choice among drug users, despite the severe health risks and legal consequences associated with its use.
Used in Research:
HEROIN DIACETYLMORPHINE is also used in scientific research to study the effects of opioids on the brain and to develop new treatments for pain management and addiction. Understanding the mechanisms of action of heroin can help researchers develop safer and more effective analgesics with fewer addictive properties.

Biological Functions

Heroin is the diacetyl derivative of morphine. It is not available in the United States for therapeutic use, although its use as a recreational drug is again on the rise. It is either injected or snorted (taken intranasally). It is most often cut, or diluted, with substances such as quinine, which contribute to the flash, or high. Injection of the drug leads to the eventual collapse of the vessels into which it is injected, leading to the appearance of track marks under the skin. Heroin passes rapidly into the brain and thus has a rapid onset of action. It is then metabolized to morphine. The rapid onset contributes to the abuse liability of the drug.Heroin use in pregnant women can lead to low-birth-weight babies, babies born addicted to heroin, immunosuppression, and an increased incidence of infections in both the mother and newborn; an increased incidence of AIDS also occurs.

Health Hazard

Heroin is a strongly habit-forming drug. Itis more potent than its parent compound,morphine, and much more potent thanopium. The toxic effects are similar tothose of morphine. An overdose can causerespiratory failure. It is a depressant anda stimulant of the central nervous system,showing a wide range of effects, rangingfrom drowsiness to distorted perceptionsand hallucinations. Toxicological problemsfrom an overdose of heroin may also leadto coma and pinpoint pupil. The toxicityof heroin may be enhanced when it iscoadministered with cocaine. Administrationof a narcotic antagonist such as naloxone ornaltrexone may be performed for therapy.A subcutaneous lethal dose in rabbits maybe 180 mg/kg. Heroin may produce harmfulreproductive effects in animals and humans.It is a controlled substance (opiate) listedunder the U.S. Code of Federal Regulations(Title 21, Part 329.1, 1308.11, 1987).

Pharmacology

Diamorphine is available for parenteral and oral use. It is more lipid soluble than morphine, affecting distribution and tissue penetration. One advantage over morphine is in seings where high concentrations are required in relatively low volumes, such as palliative care. Furthermore, when lipid solubility is important in regulating site of action (e.g. epidural, intrathecal use), some practitioners believe that diamorphine has specific advantages over morphine. Diamorphine is a prodrug. It is inactive at opioid receptors but is converted rapidly to the active metabolites 6-monoacetylmorphine (6 MAM), morphine and M-6-G. Presence of 6-MAM in urine or salvia can be used to differentiate between morphine and heroin (diamorphine) consumption. Further metabolism is similar to that of morphine; similar problems may arise in renal impairment.

Upstream product

• 463-51-4 Ketene 
• 57-27-2 MORPHIN 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 99077-83-5 ethyl [methyl(2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate] 
• 5140-28-3 3-O-acetylmorphine 
• 62812-42-4 methyl (phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosid)uronate 
• 64-31-3 morphine sulfate 
• 57-27-2 morphine 

Downstream Products

• 509-71-7 Dihydroheroin 
• 20827-47-8 3,6-diacetoxy-4,5-epoxy-morphin-7-ene-17-carbonitrile 
• 20827-47-8 3,6α-diacetoxy-4,5α-epoxy-morphin-7-ene-17-carbonitrile 
• 57-27-2 MORPHIN 
• 2784-73-8 6-monoacetylmorphine 
• 23095-84-3 [3H]-Morphine 3-sulfate 
• 58772-72-8 3,6-diacetylnormethylmorphine 
• 36418-22-1 4,5-epoxy-3-hydroxy-17-methyl-7,8-didehydro-5α,6α-morphinanyl 6-acetate hydrochloride 
• 6703-27-1 C₂₀H₂₃NO₄ 
• 20594-83-6 nalbuphine 
• 1403776-94-2 4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3,6-dibenzoate 
• 1403776-86-2 4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3-benzoate 6-acetate 
• 302965-12-4 4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3-benzoate 
• 20290-09-9 Morphine 3-b-D-glucuronide 

Relevant academic research and scientific papers

Nalbuphine preparation method and intermediate thereof

The invention discloses a nalbuphine preparation method and an intermediate thereof, and the nalbuphine is prepared by taking morphine as a raw material through acylation, catalytic oxidation, palladium/carbon hydrogenation reduction, N-methyl removal of chloroformic acid-1-chloroethyl ester, hydrolysis deprotection and nitrogen-methylcyclobutane substitution. According to the method, a chiral center is introduced from an initial raw material, in the whole reaction process, reactions and reagents which can influence the chiral center are not adopted, only conventional methods and equipment are used in the whole reaction process, and the method is easy and convenient to operate, mild in condition, short in route, high in overall yield and suitable for industrial production.

Synthetic method of morphine derivative and applications

The invention discloses a synthetic method of a morphine derivative. The method employs morphine as an initial raw material, and selective protection and glycosylation are carried out in order to obtain a target product. The HPLC purity of M3G obtained by the synthetic method reaches 99.8%, and the M3G can be used as a reference substance or a standard substance for researching quality of relatedproducts.

6-ACETYLMORPHINE ANALOGS, AND METHODS FOR THEIR SYNTHESIS AND USE

The present invention relates to novel 6-acetylmorphine analogs, and methods for their synthesis and use. Such analogs are designed to provide a convenient linkage chemistry for coupling under mild conditions to a suitable group on a target protein, polypeptide, solid phase or detectable label.

6-O-Glycosylation of morphine derivatives using thioglycosides as glycosyl donors

A novel approach was developed for the synthesis of the pharmaceutically important morphine and dihydromorphine 6-β-D-glucuronides. The key step involves a selective 6-O-glycosylation of 3-O-protected morphines and dihydromorphines with thioglycosides that serve as glycosyl donors in the presence of thiophilic promoters. This novel approach may be useful for the O-glycosylation of other alkoloid derivatives.

Selective Aminolysis of Benzoates and Acetates of α-Hydroxy Acids and Phenols with Benzylamine and Butan-1-amine

Benzoates and acetates of α-hydroxy acids and phenols undergo facile aminolysis on treating with benzylamine or butan-1-amine in benzene at room temperature.Under the same conditions acetates and benzoates of alcohols are unaffected.

Ligand determination of spin labeled compounds by receptor displacement

Compounds are provided for use in assays of organic compounds, where organic compounds of biological interest are determined at extremely low concentrations by combining in a medium, the composition to be determined, hereinafter referred to as ligand, a high molecular weight material of at least 10,000 molecular weight, which has a site spatially characterisitc of the ligand, hereinafter referred to as receptor, and an analog of the ligand having a free radical functionality hereinafter referred to as "ligand analog". The ligand analog and ligand in the medium compete for the receptor site, the amount of ligand analog bound to the receptor, being dependent on the amount of ligand present in the medium. By following the change in electron spin resonance spectrum of the ligand analog and comparing it to the change in spectrum which would be obtained in the absence of any ligand, the amount of ligand can be determined.

Spin labeled compounds

Compounds are provided for use in assays of organic compounds, where organic compounds of biological interest are determined at extremely low concentrations by combining in a medium, the composition to be determined, hereinafter referred to as ligand, a high molecular weight material of at least 10,000 molecular weight, which has a site spatially characteristic of the ligand, hereinafter referred to as receptor, and an analog of the ligand having a free radical functionality, hereinafter referred to as "ligand analog". The ligand analog and ligand in the medium compete for the receptor site, the amount of ligand analog bound to the receptor, being dependent on the amount of ligand present in the medium. By following the change in electron spin resonance spectrum of the ligand analog and comparing it to the change in spectrum which would be obtained in the absence of any ligand, the amount of ligand can be determined.