71-68-1

Basic information

• Product Name: HYDROMORPHONE HYDROCHLORIDE
• Synonyms: HYDROMORPHONE HYDROCHLORIDE OPIATE ANALG ESIC;(5α)-4,5-epoxy-3-hydroxy-17-methyl-morphinan-6-one hydrochloride;hydromorphone hydrochloride solution;HYDROMORPHONEHYDROCHLORIDE,USP;Hydromorphine hydrochloride;Morphinan-6-one, 4,5.alpha.-epoxy-3-hydroxy-17-methyl-, hydrochloride;Morphinan-6-one, 4,5-epoxy-3-hydroxy-17-methyl-, hydrochloride, (5.alpha.)-;Morphinone, dihydro-, hydrochloride
• CAS NO: 71-68-1
• Molecular Formula: C17H20ClNO3
• Molecular Weight: 321.8
• EINECS: 200-762-6
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 71-68-1.mol

Chemical Properties

• Melting Point: >280°C (dec.)
• Boiling Point: 475.6 °C at 760 mmHg
• Flash Point: 241.4 °C
• Appearance: /
• Density: 1.1451 (rough estimate)
• Vapor Pressure: 1.88E-11mmHg at 25°C
• Refractive Index: 1.6470 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: >10 mg/mL
• CAS DataBase Reference: HYDROMORPHONE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: HYDROMORPHONE HYDROCHLORIDE(71-68-1)
• EPA Substance Registry System: HYDROMORPHONE HYDROCHLORIDE(71-68-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 16-36/37-45
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• RTECS: QD2625000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 71-68-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hydromorphone Hydrochloride is used as an analgesic for the management of moderate to severe pain. Its potent pain-relieving effects make it a valuable option for patients experiencing intense discomfort or post-operative pain.
Used in Medical Applications:
Hydromorphone Hydrochloride is used as a controlled substance in the medical field to provide effective pain relief for patients with chronic or severe pain conditions. Its use is strictly regulated to prevent misuse and ensure patient safety.
Used in Pain Management:
Hydromorphone Hydrochloride is used as a potent narcotic analgesic for the treatment of various types of pain, including cancer pain, post-operative pain, and chronic pain conditions. Its strong pain-relieving properties make it a useful tool in pain management for healthcare professionals.

Biochem/physiol Actions

Narcotic opiate analgesic; μ opioid receptor agonist.

Clinical Use

Hydromorphone is a potent μ agonist (eight times greater than morphine) that is used to treat severe pain. It is available in intramuscular, intravenous, subcutaneous, oral, and rectal dosage forms. Like all strong μ agonists, hydromorphone is addicting and is a Schedule II drug. Hydromorphone has an oral:parenteral potency ratio of 5:1. The plasma half-lives after parenteral and oral dosage are 2.5 and 4 hours, respectively.

Safety Profile

Poison by subcutaneous and intravenous routes. Experimental teratogenic effects. A powerful analgesic. When heated to decomposition it emits very toxic fumes of NOx and HCl. See also MORPHINE.

Drug interactions

Potentially hazardous interactions with other drugs Alcohol: can cause dose dumping with sustained release preparations. Analgesics: possible opioid withdrawal effects with buprenorphine and pentazocine. Antidepressants: possible CNS excitation or depression with MAOIs - avoid concomitant use and for 2 weeks after stopping MAOI; possible CNS excitation or depression with moclobemide; increased sedative effects with tricyclics. Antihistamines: increased sedative effects with sedating antihistamines. Antipsychotics: enhanced hypotensive and sedative effects. Dopaminergics: avoid with selegiline. Nalmefene: avoid concomitant use. Sodium oxybate: enhanced effect of sodium oxybate - avoid.

Metabolism

Hydromorphone undergoes extensive firstpass metabolism. It is extensively metabolised by glucuronidation in the liver and excreted in the urine mainly as conjugated hydromorphone, dihydroisomorphine, and dihydromorphine.

InChI:InChI=1/C17H19NO3.2ClH/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;2*1H/t10-,11+,16-,17-;;/m0../s1

Upstream product

• 125-29-1 Hydrocodone 
• 466-99-9 hydromorphone 
• 33049-61-5 (-)-tetrahydrothebaine 
• 1421-28-9 Dihydromorphine hydrochloride 

Downstream Products

• 105618-26-6 norbinaltorphimine 
• 26626-12-0 dihydroisomorphine 
• 676324-55-3 5'-(4-chlorophenyl)-6,7-didehydro-4,5α-epoxy-3-hydroxy-17-methylpyrido[2',3':6,7]morphinan 
• 1417540-92-1 (4R,7aR,12bS)-N-(4-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenethyl)-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carboxamide 
• 1417540-81-8 (4bS,9R)-N-(4-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenethyl)-4-hydroxy-11-methyl-6-oxo-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-3-carboxamide 
• 1431530-04-9 3-aspirin-hydromorphone hydrochloride 
• 1431529-93-9 3-aspirin-hydromorphone 

Relevant articles and documents

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.

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.

Morphine alkone acid salt a refining technology of hydrogen (by machine translation)

The invention aims to overcome the defects in the prior art, and provides a new refinement method of hydromorphone acid salt. The method comprises the following steps: a. adding hydromorphone and dilute acid into a reaction kettle, and dissolving by stirring at 30-60 DEG C; cooling to 15--5 DEG C, stirring to precipitate abundant solid, adding alcohol and ether, and stirring to crystallize for 0.5-3 hours; filtering, washing until the pH value of the filtrate is 6-7, and drying in a drying oven to obtain a hydromorphone acid salt crude product; b. adding purified water into a refinement decolorization tank, heating to 30-60 DEG C, adding the hydromorphone acid salt crude product, stirring until the hydromorphone acid salt crude product is completely dissolved, adding medicinal carbon, adding dilute acid, and decolorizing at the constant temperature of 30-60 DEG C for 10-30 minutes; filtering, washing the filter cake with purified water, merging the washing liquid and filtrate, distilling under reduced pressure, refrigerating at 5+/-5 DEG C to crystallize for more than 8 hours; and filtering, washing the filter cake with 95% ethanol, drying in a drying oven to obtain the hydromorphone acid salt.

Towards an efficient preparation of hydromorphone

Dihydromorphone was prepared from morphine in high yield, excellent purity, and low residual metal content. The key steps used palladium on porous glass and a modified Oppenauer oxidation, or Wilkinson's catalyst. Georg Thieme Verlag Stuttgart ? New York.

Preparation of Saturated Ketone Morphinan Compounds by Catalytic Isomerization

The present invention provides processes for the preparation of saturated ketone morphinan compounds by catalytic isomerization. In particular, the invention provides processes for the conversion of a morphinan comprising an allyl alcohol ring moiety into a morphinan comprising a saturated ketone ring moiety by an isomerization reaction catalyzed by an allyl-transition metal catalyst.

A METHOD OF PREPARATION OF 4,5α-EPOXY-6-OXOMORPHINAN DERIVATIVES

A method of preparation of 4,5α-epoxy-6-oxomorphinan derivatives of formula (I), wherein R1 is hydrogen, methyl, or ethyl and R2 is hydrogen, methyl, cyclobutylmethyl or benzyl, in which compounds of formula (II), wherein R1 and R2 are as defined with respect to compounds (I), are isomerized into compounds of formula (I) in the presence of a mixed catalyst containing at least two elements from the group of platinum metals. The method provides the product in high yield and with low contents of impurities.