466-99-9

Usage

Uses

1. Used in Palliative Care:
Hydromorphone is used as an analgesic agent for severe pain management in palliative care settings. Its high potency makes it a suitable option for patients with severe pain that may not be adequately managed by less potent opioids.
2. Used in Non-Opioid-Naive Patients:
Hydromorphone is used as an alternative opioid for patients who have already been exposed to opioids and may require a more potent medication for effective pain management.
3. Used in Opioid Rotation:
Hydromorphone is used as a part of opioid rotation, a strategy to improve pain control and reduce side effects by switching patients to a different opioid medication.
4. Used in Research and Forensic Applications:
Hydromorphone is used as an analytical reference material categorized as an opioid. It is a metabolite of morphine and is regulated as a Schedule II compound in the United States, making it a valuable tool for research and forensic applications.
5. Used in Immediate-Release Formulations:
Hydromorphone is used in immediate-release tablet, liquid, and suppository forms for the management of moderate to severe pain.
6. Used in Sustained-Release Formulations (outside the United States):
Although the sustained-release form was removed from the U.S. market, it is still available in some countries for the management of chronic pain. However, caution must be exercised due to the potential risks associated with alcohol consumption and the sustained-release formulation.

Biological Functions

Hydromorphone is eight times as potent as morphine but has less bioavailability following oral administration. Its side effects do not differ from those of morphine but are more intense. Hydromorphone is indicated for use in severe pain and in high doses for relief of pain in opioid-addicted patients.

InChI:InChI=1/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1

Upstream product

• 52-26-6 morphine hydrochloride 
• 108-94-1 cyclohexanone 
• 556-91-2 aluminum tri-tert-butoxide 
• 108-88-3 toluene 
• 509-60-4 dihydromorphine 
• 119-61-9 benzophenone 
• 865-47-4 potassium tert-butylate 
• 71-43-2 benzene 
• 91265-75-7 3-(_tbutyldimethylsilyl)morphinone 
• 125-29-1 Hydrocodone 
• 7647-01-0 hydrogenchloride 
• 57-27-2 MORPHIN 
• 64-31-3 morphine sulfate 
• 873087-79-7 8,14-dihydrooripavine 

Downstream Products

• 65644-89-5 3,6-diacetoxy-4,5α-epoxy-17-methyl-morphin-6-ene 
• 116570-63-9 4,5α-epoxy-17-methyl-6-phenyl-morphinane-3,6α-diol 
• 40505-76-8 hydromorphone-3-glucuronide 
• 14696-23-2 Norhydromorphone 
• 93666-92-3 C₃₂H₄₃NO₉S 
• 93666-93-4 C₃₄H₄₇NO₈S₃ 
• 124319-83-1 carbonic acid ethyl ester-(4,5α-epoxy-6α-hydroxy-17-methyl-6β-phenyl-morphinan-3-yl ester) 
• 3414-84-4 6-Methylen-dihydrodesoxy-morphin 
• 5141-67-3 4,5α-epoxy-3-methoxymethoxy-17-methyl-6-methylene-morphinane 
• 509-60-4 dihydromorphine 
• 71-68-1 hydromorphone hydrochloride 
• 54934-75-7 6β-oxymorphol 

Relevant academic research and scientific papers

The intriguing effects of substituents in the N-phenethyl moiety of norhydromorphone: A bifunctional opioid from a set of "tail wags dog" experiments

(-)-N-Phenethyl analogs of optically pure N-norhydromorphone were synthesized and pharmacologically evaluated in several in vitro assays (opioid receptor binding, stimulation of [35S]GTPγS binding, forskolin-induced cAMP accumulation assay, and MOR-mediated β-arrestin recruitment assays). "Body"and "tail"interactions with opioid receptors (a subset of Portoghese's message-address theory) were used for molecular modeling and simulations, where the "address"can be considered the "body"of the hydromorphone molecule and the "message"delivered by the substituent (tail) on the aromatic ring of the N-phenethyl moiety. One compound, N-p-chlorophenethynorhydromorphone ((7aR,12bS)-3-(4-chlorophenethyl)-9-hydroxy-2,3,4,4a,5,6-hexahydro- 1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one, 2i), was found to have nanomolar binding affinity at MOR and DOR. It was a potent partial agonist at MOR and a full potent agonist at DOR with a δ/μ potency ratio of 1.2 in the ([35S]GTPγS) assay. Bifunctional opioids that interact with MOR and DOR, the latter as agonists or antagonists, have been reported to have fewer sideeffects than MOR agonists. The p-chlorophenethyl compound 2i was evaluated for its effect on respiration in both mice and squirrel monkeys. Compound 2i did not depress respiration (using normal air) in mice or squirrel monkeys. However, under conditions of hypercapnia (using air mixed with 5% CO2), respiration was depressed in squirrel monkeys.

Method for synthesizing hydromorphone

The invention discloses a method for synthesizing hydromorphone by using a continuous flow microchannel reactor. According to the method, by the temperature and the reaction speed of each module of the continuous flow microchannel reactor are controlled, a quenching is integrated into the continuous flow microchannel reactor, and by control of optimal reaction state of hydromorphone synthesis rawmaterials and a catalyst and the reaction speed, the reaction speed is improved. At the same time, through addition of the quenching module, the reaction can be promptly quenched, the precise controlof the reaction time can be achieved, over oxidation in a key step of Oppenauer Oxidation during hydromorphone synthesis can be reduced, production of by-products can be reduced, and reaction yield and hydromorphone product purity can be improved.

NEW PROCESS FOR PREPARING HYDROMORPHONE AND DERIVATIVES THEREOF

There is provided a novel process for the preparation of a compound of formula (I), wherein R1 is as described in the description, by demethylation of a corresponding O-methyl derivative.

SUPPORTED METAL CATALYST FOR THE PRODUCTION OF HYDROCODONE AND HYDROMORPHONE

The present invention relates to the process for the manufacture of hydrocodone or hydromorphone from their enol derivatives codeine and morphine respectively. Particularly, the invention discloses a metal catalyst that is used in low amount, leads to high yields and can easily be reused.

General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand

Remarkably simple IrIIIcatalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.

On the selection of an opioid for local skin analgesia: Structure-skin permeability relationships

Recent studies demonstrated that post-herpetical and inflammatory pain can be locally managed by morphine gels, empirically chosen. Aiming to rationalize the selection of the most suitable opioid for the cutaneous delivery, we studied the in vitro penetration through human epidermis of eight opioids, evidencing the critical modifications of the morphinan core. Log P, log D, solid-state features and solubility were determined. Docking simulations were performed using supramolecular assembly made of ceramide VI. The modifications on position 3 of the morphinan core resulted the most relevant in determining both physicochemical characteristics and diffusion pattern. The 3-methoxy group weakened the cohesiveness of the crystal lattice structure and increased the permeation flux (J). Computational studies emphasized that, while permeation is essentially controlled by molecule apolarity, skin retention depends on a fine balance of polar and apolar molecular features. Moreover, ChemPLP scoring the interactions between the opioids and ceramide, correlated with both the amount retained into the epidermis (Qret) and J. The balance of the skin penetration properties and the affinity potency for μ-receptors evidenced hydromorphone as the most suitable compound for the induction of local analgesia.

PREPARATION OF SATURATED KETONE MORPHINAN COMPOUNDS BY CATALYTIC ISOMERISATION

There is provided a novel process for the preparation of a compound of formula I, wherein R1, R2 and R3 are as described in the description, by conversion of a corresponding allylic alcohol.

METHODS FOR THE PREPARATION OF HYDROMORPHONE

The present application relates to methods for the preparation of morphine derivatives. In particular, the present application relates to methods for the preparation of hydromorphone from oripavine and oripavine from thebaine.

PROCESSES FOR MAKING HYDROCODONE, HYDROMORPHONE AND THEIR DERIVATIVES

Improved processes for making hydrocodone and hydromorphone as well as their 8,14-dihydrothebaine and 8,14-dihydrooripavine derivatives and salts are disclosed.

PROCESSES FOR MAKING HYDROCODONE, HYDROMORPHONE AND THEIR DERIVATIVES

Improved processes for making hydrocodone and hydromorphone as well as their 8,14-dihydrothebaine and 8,14-dihydrooripavine derivatives and salts are disclosed.