58752-60-6

Basic information

• Product Name: (5alpha,6alpha)-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl acetate
• Synonyms: (5alpha,6alpha)-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl acetate;4,5α-Epoxy-17-methylmorphinan-3,6α-diol 3-acetate
• CAS NO: 58752-60-6
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.39022
• EINECS: 261-421-5
• Mol File: 58752-60-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 494.8°Cat760mmHg
• Flash Point: 253°C
• Appearance: /
• Density: 1.35g/cm³
• CAS DataBase Reference: (5alpha,6alpha)-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (5alpha,6alpha)-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl acetate(58752-60-6)
• EPA Substance Registry System: (5alpha,6alpha)-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl acetate(58752-60-6)

Safety Data

• Hazardous Substances Data: 58752-60-6(Hazardous Substances Data)

Usage

Description

(5alpha,6alpha)-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl acetate, commonly known as 6-acetylmorphine or heroin, is a semi-synthetic opioid analgesic derived from morphine. It is characterized by its rapid onset of action and potent analgesic effect, making it a powerful narcotic for pain management. However, its high potential for abuse and addiction has led to its classification as a Schedule I controlled substance in the United States.

Uses

Used in Pharmaceutical Industry:
(5alpha,6alpha)-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl acetate is used as a potent analgesic for the management of severe pain. Its rapid onset of action and strong pain-relieving effects make it a valuable asset in medical settings, particularly for patients experiencing acute or chronic pain that does not respond well to other treatments.
Used in Illicit Drug Trade:
Despite its medical applications, (5alpha,6alpha)-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl acetate is also used illicitly as a recreational drug under various street names such as "heroin" and "smack". Its strong euphoric effects and high potential for abuse have made it a popular choice among drug users, contributing to its classification as a Schedule I controlled substance and the strict regulation of its production and distribution.

Upstream product

• 507-09-5 tiolacetic acid 
• 509-60-4 dihydromorphine 
• 108-24-7 acetic anhydride 
• 5140-28-3 3-O-acetylmorphine 
• 1421-28-9 Dihydromorphine hydrochloride 
• 33049-61-5 (-)-tetrahydrothebaine 
• 71-68-1 hydromorphone hydrochloride 
• 466-99-9 hydromorphone 

Downstream Products

• 130178-43-7 6-β-<5-nitro-2-pyridinesulfenyl>thio-dihydromorphine 
• 26626-12-0 dihydroisomorphine 
• 1403776-89-5 4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 6-benzoate 
• 1403776-90-8 4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3-acetate 6-benzoate 
• 14696-23-2 Norhydromorphone 

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.

Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners

A series of 3-O-acyl-6-O-sulfate esters of morphine, dihydromorphine, N-methylmorphinium iodide, codeine, and dihydrocodeine were prepared and evaluated for their ability to bind to μ-, δ-, κ1-, κ2-, and κ3-opiate receptors. Several compounds exhibited good affinity for the μ-opiate receptor. Morphine-3-O-propionyl-6-O-sulfate had four times greater affinity than morphine at the μ-opiate receptor and was the most selective compound at this receptor subtype.

New method for the preparation of dihydro-6-desoxymorphine.

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