467-04-9 Usage
Description
(5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol, also known as Oripavine, is an alkaloid derived from thebaine, a major metabolite of the opium poppy. It is a colorless needle-like crystalline compound with a light tan solid appearance. Oripavine is readily soluble in chloroform, sparingly soluble in ethanol and acetone, and insoluble in water. It exhibits optical activity as a levorotatory compound with a specific rotation of [α]D 211.8° (CHCl3). (5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol forms a hydrochloride salt with a melting point of 258-9°C (dec.) and a methiodide salt with a melting point of 207-8°C. Oripavine also dissolves in aqueous sodium hydroxide, yielding a crystalline sodium derivative.
Uses
1. Used in Pharmaceutical Industry:
(5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol is used as an intermediate compound in the synthesis of various pharmaceuticals, particularly for the production of semi-synthetic opioids. Its analgesic potency is comparable to morphine, but its clinical use is limited due to severe toxicity and low therapeutic index.
2. Used in Research and Development:
Oripavine serves as a valuable compound in the research and development of new drugs, particularly in the field of pain management and opioid pharmacology. Its unique chemical structure and properties make it an interesting subject for further investigation and potential modification to improve its therapeutic profile and safety.
3. Used in Analytical Chemistry:
As a chiral compound, (5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol can be utilized in analytical chemistry for the development of new methods and techniques for the separation and analysis of enantiomers, which is crucial in the pharmaceutical industry to ensure the purity and efficacy of chiral drugs.
4. Used in Toxicology Studies:
Due to its high toxicity and low therapeutic index, Oripavine can be employed in toxicology studies to better understand the mechanisms of action and potential risks associated with its use, as well as to develop strategies for mitigating its toxic effects.
References
Yunusov, Konovalova, Orekhov., Ber., 68,2158 (1935) Yunusov, Konovalova, Orekhov.,J. Gen. Chern. USSR, 10,641 (1940)Kiselev, Konovalova., ibid, 18,142 (1948)
Check Digit Verification of cas no
The CAS Registry Mumber 467-04-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 7 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 467-04:
(5*4)+(4*6)+(3*7)+(2*0)+(1*4)=69
69 % 10 = 9
So 467-04-9 is a valid CAS Registry Number.
InChI:InChI=1/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3/t12-,17+,18+/m1/s1
467-04-9Relevant articles and documents
Identification of fluorinated (R)-(?)-aporphine derivatives as potent and selective ligands at serotonin 5-HT2C receptor
Xu, Yulong,Sromek, Anna W.,Neumeyer, John L.
, p. 230 - 233 (2019)
A series of novel aporphine derivatives were synthesized for initial screening at the 5-HT2 receptor subtypes. Among them, Compounds 11a and 11b were identified as potent 5-HT2C hit ligands with high selectivity over other 5-HT2 receptor subtypes. Molecular docking study revealed that compounds 11a and 11b formed two key interactions with the binding site of 5-HT2C receptor, including a salt-bridge to D3.32 and a H-bond interaction with N6.55.
Synthesis and neuropharmacological evaluation of esters of R(-)-N-alkyl-11-hydroxy-2-methoxynoraporphines
Si, Yu-Gui,Choi, Yong-Kee,Gardner, Matthew P.,Tarazi, Frank I.,Baldessarini, Ross J.,Neumeyer, John L.
, p. 51 - 53 (2009)
We synthesized several esters of R(-)-N-alkyl-11-hydroxy-2-methoxynoraporphines, assessed their affinities at dopamine D1 and D2 receptors in rat forebrain tissue and quantified their effects on motor activity in normal adult male rats. Tested compounds displayed moderate to high affinities to D2 receptors but low affinities to D1 receptors. The most D2-potent (Ki = 18.9 nM) and selective novel agent (>529-fold vs D1 sites) was R(-)-2-methoxy-11-acetyloxy-N-n-propylnoraporphine (compound 4b). At moderate doses, the compound proved to have prolonged behavioral locomotor activity.
METHODS FOR THE PREPARATION OF HYDROMORPHONE
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Paragraph 0099; 0101, (2015/09/22)
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.
METHOD OF PREPARING BUPRENORPHINE
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Paragraph 0143; 0154, (2014/09/03)
An improved process for preparing buprenorphine and a method for increasing the yield of buprenorphine or a derivative thereof.
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