Oripavine

Base Information Edit

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

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Chemical Property of Oripavine Edit

Chemical Property:

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:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

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
Description This 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.
Uses The 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.

Technology Process of Oripavine

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:

synthetic route:

Reference yield: 78.0%

: (4R,4aS,7S,7aR,12bS,14R)-9-Hydroxy-7-methoxy-3-methyl-1,2,3,4,7,7a-hexahydro-4a,7-(epithiomethano)-4,12-methanobenzofuro[3,2-e]isoquinoline-14-carbonitrile

: 467-04-9
oripavine

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; at 20 ℃; Reflux;
DOI:10.1002/adsc.201400445

Reference yield: 65.0%

: (4R,4aS,7S,7aR,12bS,14S)-9-Hydroxy-7-methoxy-3-methyl-1,2,3,4,7,7a-hexahydro-4a,7-(epithiomethano)-4,12-methanobenzofuro[3,2-e]isoquinoline-14-carbonitrile

: 467-04-9
oripavine

Guidance literature:: With 2,3-dimethyl-buta-1,3-diene; In dimethyl sulfoxide; at 75 ℃; for 24h; Inert atmosphere; Sealed tube;
DOI:10.1002/adsc.201400445