509-71-7

Basic information

• Product Name: Dihydroheroine
• Synonyms: Diacetyldihydromorphine;Dihydroheroine;4,5α-Epoxy-17-methylmorphinan-3,6α-diol diacetate;Dihydroheroin;Paralaudin
• CAS NO: 509-71-7
• Molecular Formula: C₂₁H₂₅NO₅
• Molecular Weight: 371.4269
• Mol File: 509-71-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 165-167°
• Boiling Point: 496.9°Cat760mmHg
• Flash Point: 254.3°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 5.19E-10mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: Dihydroheroine(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydroheroine(509-71-7)
• EPA Substance Registry System: Dihydroheroine(509-71-7)

Safety Data

• Hazardous Substances Data: 509-71-7(Hazardous Substances Data)

Usage

General Description

Dihydroheroin, also known as 6-acetylmorphine or diacetylmorphine, is a semi-synthetic opioid drug derived from morphine. It is produced by chemically modifying morphine, leading to increased potency and faster onset of action. Dihydroheroin is a powerful central nervous system depressant, and like other opioids, it acts by binding to opioid receptors in the brain and spinal cord, resulting in analgesic, sedative, and euphoric effects. It is commonly used as a recreational drug due to its highly addictive nature and potential for abuse. Long-term use of dihydroheroin can lead to physical dependence, tolerance, and severe withdrawal symptoms upon cessation. Additionally, misuse of dihydroheroin can lead to numerous adverse effects including respiratory depression, overdose, and death. Due to these risks, the use of dihydroheroin is highly regulated and restricted.

InChI:InChI=1/C21H25NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4,6,14-15,17,20H,5,7-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1

Upstream product

• 561-27-3 Diamorphine 
• 108-24-7 acetic anhydride 

Downstream Products

• 1268252-32-9 C₁₇H₂₁NO₆S 
• 66641-10-9 6-Acetyldihydromorphine 
• 509-60-4 dihydromorphine 
• 302965-12-4 4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3-benzoate 
• 1403776-86-2 4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3-benzoate 6-acetate 
• 1403776-94-2 4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3,6-dibenzoate 
• 1421-13-2 dihydronormorphine 

Relevant articles and documents

Preparation of benzoate esters of morphine and its derivatives

Sustained analgesia is crucial for patients suffering from long-acting pain. Ester derivatives of morphine could enhance the lipophilicity of morphine; consequently its transdermal delivery as well as its duration of action are also increased. Therefore, twenty-one 3-O-, 6-O-, and 14-Obenzoate esters of morphine and their derivatives were synthesized in order to elaborate different synthetic methods suitable for esterification of these widely used compounds. Schotten-Baumann reaction was applied with sodium hydrogen carbonate, triethylamine, or pyridine in methylene chloride or 1,2-dichloroethane as solvents. The presence of 4-dimethylaminopyridine catalyst was also successfully utilized mainly in the case of tertiary alcohols. A novel synthesis of dihydromorphine via diacetyl morphine free of by-products is also presented. Structures of all synthesized compounds were elucidated by 1H nuclear magnetic resonance (NMR), 13CNMR, high-resolution mass spectrometry (HRMS), and electron ionizationmass spectrometry (EI-MS). The log D (pH 7.4) values of the synthesized compounds were determined by a reversed-phase high-performance liquid chromatography (HPLC)-MS-based method, and calculated hydrolysis rate constants are also provided. The synthesized benzoate esters are potential prodrugs of the parent morphine with enhanced lipophilicity, derivatives which can also be used in transdermal drug delivery as prospective long-acting narcotic analgesics.