(4R,4aS,7aR)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one

Base Information

• Chemical Name: (4R,4aS,7aR)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
• CAS No.: 16590-41-3
• Molecular Formula: C20H23 N O4
• Molecular Weight: 341.407
• Hs Code.: 2939190000
• NSC Number: 758439
• Wikidata: Q27163610
• Mol file: 16590-41-3.mol

Synonyms:Spectrum_001645;Spectrum2_001547;Spectrum3_001587;Spectrum4_000639;Spectrum5_000976;BSPBio_003154;KBioGR_001258;KBioSS_002125;DivK1c_000547;SPECTRUM1503262;SPBio_001394;SCHEMBL13050619;CHEBI:91813;HMS501L09;KBio1_000547;KBio2_002125;KBio2_004693;KBio2_007261;KBio3_002654;NINDS_000547;HMS1922O07;HMS2093A17;Pharmakon1600-01503262;CCG-39325;NSC758439;IDI1_000547;NCGC00178236-02;SBI-0051807.P002;AB00052339_02;SR-05000001848;SR-05000001848-1;BRD-A66559694-001-01-2;BRD-A66559694-001-03-8;Q27163610;(4R,4aS,7aR)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one

Chemical Property of (4R,4aS,7aR)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one

Chemical Property:

• Appearance/Colour: Crystals from acetone.
• Vapor Pressure: 2.71E-13mmHg at 25°C
• Melting Point: 168-170°
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 558.1°C at 760 mmHg
• PKA: pKa 8.38/8.13(H2O,t =20/37,I<0.01) (Uncertain)
• Flash Point: 291.4°C
• PSA: 70.00000
• Density: 1.47g/cm³
• LogP: 1.46330
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 621

Purity/Quality:

99%, ^*data from raw suppliers

Naltrexone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1CN2CCC34C5C(=O)CCC3(C2CC6=C4C(=C(C=C6)O)O5)O
• Isomeric SMILES: C1CC1CN2CCC34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O
• Description: This drug does not have agonistic properties. It is similar to naloxone in terms of pharmacological characteristics; however, it differs in two important ways—long-lasting action and that its metabolite 6-β-naltrexol is also a strong antagonist. Naltrexone is potentially hepatotoxic. Naltrexone is used for blocking pharmacological effects of opioids upon their overdose.
• Uses: Naltrexone is an opioid antagonist shown to reduce the occurrence of addictive behaviours such as eating, smoking and drinking excessively. in addition to curbing drug use it has recently been used in flavor avoidance studies. anthelmintic, teniacide Labeled Naltrexone, intended for use as an internal standard for the quantification of Naltrexone by GC- or LC-mass spectrometry.
• Indications: Naltrexone, an orally active opioid receptor antagonist, restores erectile function in some patients with idiopathic ED.
• Therapeutic Function: Narcotic analgesic
• Biological Functions: Naltrexone (Trexan) is three to five times as potent as naloxone and has a duration of action of 24 to 72 hours, depending on the dose. It is used orally in the treatment of opioid abstinence. Naltrexone exhibits a large firstpass effect in the liver. However, the major metabolite, 6-β-naltrexol, is also a pure opioid antagonist and contributes to the potency and duration of action of naltrexone. Administration of naltrexone orally blocks the subjective effects of abused opioids and is used to decrease the craving for opioids in highly motivated recovering addicts. However, high doses of the opioids can overcome the naltrexone blockade and lead to seizures or respiratory depression and death. In addition, it has been reported recently that naltrexone can reduce the craving for alcohol in alcoholic patients. Naltrexone also has been used with success in treating apneic episodes in children, an effect hypothesized to be due to blockade of β-endorphin–induced respiratory depression. Naltrexone can induce hepatotoxicity at doses only five times the therapeutic dose and should be used with care in patients with poor hepatic function or liver damage. Side effects of the use of naltrexone are more frequently observed than following naloxone administration. Such side effects include headache, difficulty sleeping, lethargy, increased blood pressure, nausea, sneezing, delayed ejaculation, blurred vision, and increased appetite.

Technology Process of (4R,4aS,7aR)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one

There total 71 articles about (4R,4aS,7aR)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.45%

noroxymorphone (33522-95-1) + cyclopropylcarbinyl bromide (7051-34-5) → Naltrexone (16590-41-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1-ethyl-2-pyrrolidinone; at 52 - 57 ℃; for 24.75h; Product distribution / selectivity;

Reference yield: 97.0%

naltrexone hydrochloride → Naltrexone (16590-41-3)

Guidance literature:

In ethanol; at -10 ℃;

Reference yield: 95.0%

(4R,7aR,12bS)-3-(cyclopropylmethyl)-7-methoxy-2,3,4,7a-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol (14728-69-9) → Naltrexone (16590-41-3)

Guidance literature:

(4R,7aR,12bS)-3-(cyclopropylmethyl)-7-methoxy-2,3,4,7a-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol; With peracetic acid; In water; acetic acid; at 5 - 20 ℃; for 0.616667h;

With hydrogen; palladium 10% on activated carbon; In water; acetic acid; isopropyl alcohol; for 15h; under 2585.81 Torr;

upstream raw materials:

naltrexone methyl ether

noroxymorphone

Cyclopropanecarboxaldehyde

C₃₅H₃₇ClN₂O₈

Downstream raw materials:

nalmefene

β-naltrexol

6alpha-Naltrexol

N-(6α-naltrexyl)-N'-(tert-butoxycarbonyl)-p-phenylenediamine

Refernces

Fischer indole synthesis in water: Simple, efficient preparation of naltrindole, naltriben and analogs

10.1039/b920864j

The research presents an environmentally friendly method for synthesizing naltrindole (NTI), naltriben (NTB), and their analogs using Fischer indole synthesis under mildly acidic, purely aqueous conditions. The study explores the preparation of these compounds, which are valuable tools for opioid receptor pharmacology studies, using hydrochloride salts of naltrexone and various phenylhydrazines in boiling water, achieving good to excellent yields and high purities without the need for organic solvents or harsh acids. The chemicals that played a crucial role in this research include naltrexone hydrochloride (NTX·HCl), phenylhydrazine hydrochloride, and other substituted phenylhydrazines such as 1-methyl-1-phenylhydrazine, o-chlorophenylhydrazine, o-fluorophenylhydrazine, and o-nitrophenylhydrazine. The study also utilized dilute hydrochloric acid (HCl) to facilitate the synthesis, and in some cases, sulfuric acid (H?SO?) for comparison. The products were obtained through simple filtration or centrifugation, highlighting the simplicity and efficiency of the aqueous Fischer synthesis method.

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