Buy Oripavine powder Cas-467-04-9
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Oripavine is an opioid and the major metabolite of thebaine. It is the precursor to the semi-synthetic compounds etorphine and buprenorphine. Although this chemical compound has analgesic potency comparable to morphine, it is not used clinically due to severe adverse effects and a low therapeutic index. Being a precursor to a series of extremely strong opioids, oripavine is a controlled substance in some jurisdictions. Buy Oripavine powder Cas-467-04-9
Pharmacological properties
Oripavine possesses an analgesic potency comparable to morphine; however, it is not clinically useful due to severe toxicity and low therapeutic index. In both mice and rats, toxic doses caused tonic-clonic seizures followed by death, similar to thebaine.[1] Oripavine has a potential for dependence which is significantly greater than that of thebaine but slightly less than that of morphine.[2]
Bridged derivatives (The Bentley compounds)
Of much greater relevance are the properties of the orvinols, a large family of semi-synthetic oripavine derivatives classically synthesized by the Diels-Alder reaction of thebaine with an appropriate dienophile followed by 3-O-demethylation to the corresponding bridged oripavine. These compounds were developed by the group led by K. W. Bentley in the 1960s, and these Bentley compounds represent the first series of “super-potent” μ-opioid agonists, with some compounds in the series being over 10,000 times the potency of morphine as an analgesic.[3][4][5] The simple bridged oripavine parent compound 6,14-endoethenotetrahydrooripavine is already 40 times the potency of morphine,[6] but adding a branched tertiary alcohol substituent on the C7 position results in a wide range of highly potent compounds.[7]
| Drug name | R | Analgesic Potency (Morphine = 1) |
|---|---|---|
| isobutyl | 10 | |
| phenyl | 34 | |
| n-hexyl | 58 | |
| methyl | 63 | |
| cyclopentyl | 70 | |
| ethyl | 330 | |
| phenethyl | 2200 | |
| Etorphine | n-propyl | 3200 |
| TL 2636 | cyclohexyl | 3400 |
| n-pentyl | 4500 | |
| n-butyl | 5200 | |
| M-140 | isopentyl | 9200 |
Other notable derivatives then result from further modification of this template, with saturation of the 7,8-double bond of etorphine resulting in the even more potent dihydroetorphine (up to 12,000× potency of morphine) and acetylation of the 3-hydroxy group of etorphine resulting in acetorphine (8700× morphine). While the isopentyl homologue of etorphine, known as M-140, is nearly three times more potent, its 7,8-dihydro and 3-acetyl derivatives are less potent than the corresponding derivatives of etorphine at 11,000 and 1300 times morphine, respectively. Replacing the N-methyl group with cyclopropylmethyl results in opioid antagonists such as diprenorphine (M5050, which is used as an antidote to reverse the effects of etorphine, M99), and partial agonists such as buprenorphine, which is widely used in the treatment of opioid addiction, although conversely the N-cyclopropylmethyl derivative of M-140, which has the code number M-320, retains similarly potent μ-opioid full agonist activity to the N-methyl derivative. More complex substitutions on the ring system can be used to produce selective δ-opioid agonists such as BU-48, and selective κ-opioid agonists such as CL 110,393.
Legal status
Due to the relative ease of synthetic modification of oripavine to produce other narcotics (by either direct or indirect routes via thebaine), the World Health Organization‘s Expert Committee on Drug Dependence recommended in 2003 that oripavine be controlled under Schedule I of the 1961 Single Convention on Narcotic Drugs.[8] On March 14, 2007, the United Nations Commission on Narcotic Drugs formally decided to accept these recommendations, and placed oripavine in the Schedule I. Buy Oripavine powder Cas-467-04-9
Until recently, oripavine was a Schedule II drug in the United States by default as a thebaine derivative, although it was not explicitly listed. However, as a member state under the 1961 Single Convention on Narcotic Drugs, the US was obliged to specifically control the substance under the Controlled Substances Act following its international control by the UN Commission on Narcotic Drugs. On September 24, 2007, the Drug Enforcement Administration formally added oripavine to Schedule II.[10]
Under the Controlled Substances Act 1970, oripavine has an ACSCN of 9330 and a 2013 manufacturing quota of 22,750 kg (50,160 lb).
What Is Oripavine? A Potent Opioid Precursor
Oripavine is a naturally occurring opioid alkaloid found in certain poppy species. Its primary significance lies in its role as a chemical precursor. This compound is not commonly used as a direct therapeutic agent or illicit drug. Instead, its chemical structure allows for its transformation into other potent substances. Buy Oripavine powder Cas-467-04-9
Understanding Oripavine’s Origins
Oripavine is an alkaloid extracted from the opium poppy, Papaver somniferum, and also occurs as a major alkaloid in Papaver orientale. It is found alongside more abundant compounds such as morphine and thebaine in the opium poppy. Historically, poppy farming has been the commercial source, with specific cross-bred cultivars producing higher levels of oripavine.
Chemically, oripavine belongs to the morphinan class of opioids and is considered the major metabolite of thebaine, indicating its position within the biosynthetic pathway of these plant-derived compounds. Recent developments include biosynthetic production methods using yeast strains, offering an alternative to agricultural extraction.
Oripavine’s Role in Drug Development
Oripavine is valued in the pharmaceutical industry as a precursor for the semi-synthetic production of potent opioids. Its chemical structure allows for modifications that lead to a range of powerful derivatives, making it a key starting material for many active pharmaceutical ingredients.
One such derivative is etorphine, an opioid significantly more potent than morphine, often utilized in veterinary medicine for tranquilizing large animals. Another important compound derived from oripavine is buprenorphine, which serves in pain management and the treatment of opioid addiction.
Potency and Health Considerations
Oripavine exhibits high potency, with analgesic effects comparable to morphine. However, it is not used clinically due to severe adverse effects and a low therapeutic index.
Studies in mice and rats have shown that toxic doses can lead to tonic-clonic seizures, similar to the effects observed with thebaine. If ingested or abused, oripavine presents significant health risks, including severe respiratory depression and central nervous system depression. There is also a high risk of overdose associated with its use. Furthermore, oripavine has a strong potential for dependence, which is considered greater than that of thebaine, though slightly less than morphine.
Legal Classification and Control
Oripavine is a controlled substance in many countries due to its potential for abuse and its role as a precursor in synthesizing potent opioids. In the United States, it is classified as a Schedule II controlled substance under the Controlled Substances Act (21 U.S.C. § 812). This classification applies because it is considered a derivative of thebaine, a natural constituent of opium.
Legitimate use is generally restricted to licensed research and pharmaceutical manufacturing settings. The Drug Enforcement Administration formally added oripavine to Schedule II on September 24, 2007, following recommendations for international control.
Oripavine
- Chemical Name:Oripavine
- CAS No.:467-04-9
- Molecular Formula:C18H19NO3
- Molecular Weight:297.354
- Hs Code.:
- European Community (EC) Number:207-385-6
- UNII:575AOU51CR
- DSSTox Substance ID:DTXSID10196908
- Nikkaji Number:J12.064B
- Wikipedia:Oripavine
- Wikidata:Q420639
- ChEMBL ID:CHEMBL437602
- Mol file:467-04-9.mol
Synonyms:6-demethoxythebaine;O(3)-dimethylthebaine;oripavine;oripavine hydrochloride, (5alpha)-isomer
This product is a nationally controlled contraband, and the Lookchem platform doesn’t provide relevant sales information.
- Vapor Pressure:7.41E-10mmHg at 25°C
- Melting Point:181-186°C (dec.)
- Boiling Point:480.5°C at 760 mmHg
- PKA:9.28±0.40(Predicted)
- Flash Point:244.4°C
- PSA：41.93000
- Density:1.38g/cm3
- LogP:2.05940
- Storage Temp.:Controlled Substance, -20°C Freezer
- XLogP3:1.9
- Hydrogen Bond Donor Count:1
- Hydrogen Bond Acceptor Count:4
- Rotatable Bond Count:1
- Exact Mass:297.13649347
- Heavy Atom Count:22
- Complexity:571
- Purity/Quality:
- Pictogram(s):
- Hazard Codes:
- MSDS Files:
- SDS file from LookChem
- Canonical SMILES:CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)O)O4)OC
- Isomeric SMILES:CN1CC[C@]23[C@@H]4C(=CC=C2[C@H]1CC5=C3C(=C(C=C5)O)O4)OC
- DescriptionThis alkaloid was first obtained from the leaves of Papaver orientalis by moistening the dried leaves with ammonia and extracting them with CH2CI2. Subsequently it has been isolated from P. bracteaturn and on recrystallization from EtOH it forms colourless needles. It is readily soluble in CHCI3, sparingly so in EtOH and Me2CO and insoluble in H20. It is laevorotatory with [α]D – 211.8° (CHC13) and yields a hydrochloride, m.p. 258-9°C (dec.) and a methiodide, m.p. 207-8°C. The alkaloid dissolves in aqueous NaOH yielding a crystalline sodium derivative.
- UsesThe major metabolite of Thebaine. Oripavine possesses an analgesic potency comparable to Morphine; it is not clinically useful due to severe toxicity and low therapeutic index. An opiate.
There total 13 articles about Oripavine 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:
Reference yield: 78.0%
- Guidance literature:
-
With 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; at 20 ℃; Reflux;
Reference yield: 65.0%
- Guidance literature:
-
With 2,3-dimethyl-buta-1,3-diene; In dimethyl sulfoxide; at 75 ℃; for 24h; Inert atmosphere; Sealed tube;
- Guidance literature:
-
With L-Selectride; In tetrahydrofuran; for 336h; Ambient temperature;
- upstream raw materials:
- 3-acetyloripavine
- Downstream raw materials:
- thebaine
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