Racemorphan: Difference between revisions

Racemorphan
Identifiers
	IUPAC name (±)-17-methylmorphinan-3-ol;
CAS Number	297-90-5 ; 5985-35-3 (HBr);
ChemSpider	16736212;
UNII	V7R79HN3XD;
ECHA InfoCard	100.005.499
Chemical and physical data
Formula	C17H23NO
Molar mass	257.37 g/mol g·mol−1

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Revision as of 13:04, 17 December 2014

Racemorphan is the racemic mixture of the two stereoisomers of 17-methylmorphinan-3-ol, each with differing pharmacology and effects:

Dextrorphan - A dissociative hallucinogen (NMDA receptor antagonist) and cough suppressant.
Levorphanol - A potent opioid analgesic.

Synthesis

Cyclohexanone is condensed with cyanoacetic acid (Knovenagel reaction), during which a simultaneous decarboxylation occurs, forming 1-cyclohexenylacetonitrile.^[1] Reduction of the nitrile group by hydrogen in the presence of Raney cobalt gives 2-(1-cyclohexenyl)ethylamine. The resulting amine is further acylated by 4-anisoyl acetyl chloride

Also note:^[2]^[3]

References

^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.15227/orgsyn.031.0025, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.15227/orgsyn.031.0025 instead.
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/hlca.19490320325, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1002/hlca.19490320325 instead.
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/hlca.19500330606, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1002/hlca.19500330606 instead.

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[1] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.15227/orgsyn.031.0025, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.15227/orgsyn.031.0025 instead.

[2] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/hlca.19490320325, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1002/hlca.19490320325 instead.

[3] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/hlca.19500330606, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1002/hlca.19500330606 instead.

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 * [[Levorphanol]] - A [[potent (pharmacology)|potent]] [[opioid]] [[analgesic]].
 ==Synthesis==
-Cyclohexanone is condensed with cyanoacetic acid ([[Knoevenagel reaction]]), during which a simultaneous decarboxylation occurs, forming 1-cyclohexenylacetonitrile.<ref>{{Cite doi|10.15227/orgsyn.031.0025}}</ref> Reduction of the nitrile group by hydrogen in the presence of Raney [[cobalt]] gives 2-(1-cyclohexenyl)ethylamine.
+Cyclohexanone is condensed with cyanoacetic acid ([[Knovenagel reaction]]), during which a simultaneous decarboxylation occurs, forming 1-cyclohexenylacetonitrile.<ref>{{Cite doi|10.15227/orgsyn.031.0025}}</ref> Reduction of the nitrile group by hydrogen in the presence of Raney [[cobalt]] gives 2-(1-cyclohexenyl)ethylamine. The resulting amine is further acylated by 4-[[anisoyl]] [[acetyl chloride]]
 Also note:<ref>{{Cite doi|10.1002/hlca.19490320325}}</ref><ref>{{Cite doi|10.1002/hlca.19500330606}}</ref>
 == See also ==
 * [[Methorphan]]