509-71-7

Usage

Uses

Dihydroheroin is used as a recreational drug for its highly addictive nature and potential for abuse. However, due to its risks, including physical dependence, tolerance, severe withdrawal symptoms, respiratory depression, overdose, and death, its use is highly regulated and restricted. There are no legitimate medical applications for dihydroheroin, and it is not used in any industry for any specific reason.

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 academic research and scientific papers

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.