Racemorphan: Difference between revisions

Racemorphan
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; US: Schedule II; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name (±)-17-Methylmorphinan-3-ol;
CAS Number	297-90-5 ; 5985-35-3 (HBr);
PubChem CID	3918;
ChemSpider	3781;
UNII	V7R79HN3XD;
ChEMBL	ChEMBL20803;
ECHA InfoCard	100.005.499
Chemical and physical data
Formula	C17H23NO
Molar mass	257.377 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC23CCCCC2C1Cc4ccc(O)cc34;
	InChI InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3; Key:JAQUASYNZVUNQP-UHFFFAOYSA-N;

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

Dextrorphan – an antitussive and dissociative hallucinogen (NMDA receptor antagonist)
Levorphanol – an opioid analgesic

Racemorphan itself is under international control per the Single Convention on Narcotic Drugs 1961 and is therefore listed as a Schedule II Narcotic controlled substance in the US Controlled Substances Act 1970; it has an ACSCN of 9733 and in 2014 it had an aggregate annual manufacturing quota of zero. ^[2] The salts in use are hydrobromide (free base conversion ratio 0.741), hydrochloride (0.876), and tartrate (0.632).

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ "Conversion Factors for Controlled Substances". www.deadiversion.usdoj.gov.

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[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] "Conversion Factors for Controlled Substances". www.deadiversion.usdoj.gov.

[1]

[2]

@@ Line 1: / Line 1: @@
+{{Short description|Racemic mixture}}
-{{Distinguish|Morphan}}
+{{Distinguish|racemethorphan|morphan}}
 {{Drugbox
-| IUPAC_name = (±)-17-methylmorphinan-3-ol
+| IUPAC_name = (±)-17-Methylmorphinan-3-ol
 | image = Racemorphan.svg
 | width = 250
@@ Line 7: / Line 8: @@
 <!--Clinical data-->
 | tradename =
 | pregnancy_category =
-| legal_status =
+| legal_AU = S9
+| legal_BR = A1
+| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
+| legal_CA = Schedule I
+| legal_DE = Anlage II
+| legal_UK = Class A
+| legal_UN = P I
+| legal_US = Schedule II
 | routes_of_administration =
@@ Line 23: / Line 31: @@
 | ATC_prefix =
 | ATC_suffix =
-| PubChem =
+| PubChem = 3918
-| ChemSpiderID = 16736212
+| ChemSpiderID = 3781
 | UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = V7R79HN3XD
+| ChEMBL = 20803
 <!--Chemical data-->
 | C=17 | H=23 | N=1 | O=1
+| StdInChI = 1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3
-| molecular_weight = 257.37 g/mol
+| StdInChIKey = JAQUASYNZVUNQP-UHFFFAOYSA-N
+| smiles = CN1CCC23CCCCC2C1Cc4ccc(O)cc34
 }}
-'''Racemorphan''' is the [[racemic mixture]] of the two [[stereoisomer]]s of 17-methylmorphinan-3-ol, each with differing [[pharmacology]] and [[therapeutic effect|effect]]s:
+'''Racemorphan''', or '''morphanol''', is the [[racemic mixture]] of the two [[stereoisomer]]s of 17-methylmorphinan-3-ol, each with differing [[pharmacology]] and [[therapeutic effect|effect]]s:
-* [[Dextrorphan]] - an [[antitussive]] and  [[dissociative drug|dissociative]] [[hallucinogen]] ([[NMDA receptor antagonist]])
+* [[Dextrorphan]]{{snd}} an [[antitussive]] and  [[dissociative drug|dissociative]] [[hallucinogen]] ([[NMDA receptor antagonist]])
-* [[Levorphanol]] - an [[opioid]] [[analgesic]]
+* [[Levorphanol]]{{snd}} an [[opioid]] [[analgesic]]
+Racemorphan itself is under international control per the Single Convention on Narcotic Drugs 1961 and is therefore listed as a Schedule II Narcotic controlled substance in the US Controlled Substances Act 1970; it has an ACSCN of 9733 and in 2014 it had an aggregate annual manufacturing quota of zero. <ref>{{cite web|url=http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html|title=Conversion Factors for Controlled Substances|website=www.deadiversion.usdoj.gov}}</ref>  The salts in use are hydrobromide (free base conversion ratio  0.741), hydrochloride (0.876), and tartrate (0.632).
-==Synthesis==
-[[File:Racemorphan synthesis.svg|thumb|center|700px|Racemorphan synthesis:<ref>{{Cite journal | doi = 10.1002/hlca.19490320325| pmid = 18129560| title = Synthese von Oxy-morphinanen| journal = Helvetica Chimica Acta| volume = 32| issue = 3| pages = 821| year = 1949| last1 = Schnider | first1 = O.| last2 = Grüssner | first2 = A.}}</ref><ref>{{Cite journal | doi = 10.1002/hlca.19500330606| title = Synthese von Morphinanen. (2. Mitteilung)| journal = Helvetica Chimica Acta| volume = 33| issue = 6| pages = 1437| year = 1950| last1 = Schnider | first1 = O.| last2 = Hellerbach | first2 = J.}}</ref>]]
-One of the syntheses starts by the [[Knoevenagel condensation]] of [[cyclohexanone]] with ethyl cyanoacetate, [[hydrolysis]] of which leads to the corresponding [[cyano acid]]. The latter loses [[carbon dioxide]] under reaction conditions to give 1-cyclohexenylacetonitrile.<ref>{{Cite journal | author=Submitted by A. C. Cope, A. A. D'Addieco, D. E. Whyte, and S. A.Glickman. Checked by T. L. Cairns and R. E. Heckert.  | year = 1951 | title = CYCLOHEXYLIDENECYANOACETIC ACID AND 1-CYCLOHEXENYLACETONITRILE [Δ1,α-Cyclohexaneacetic acid,α-cyano-, and 1-Cyclohexene-1-acetonitrile] | journal = Organic Syntheses | volume = 31 | issue =  | pages = 25 | publisher =  | jstor =  | doi = 10.15227/orgsyn.031.0025 | url =  | format =  | accessdate = }}</ref> The out-of-conjugation shift of the olefin is a direct consequence of the mechanism of the decarboxylation reaction.
-Treatment of the [[nitrile]] with [[lithium aluminium hydride]] then leads to the primary amine, or alternatively the nitrile can be selectively reduced with hydrogen over [[Raney cobalt]].
-Acylation with ''p''-[[anisoyl]] [[acetyl chloride]] adds the aromatic ring required for the [[morphinan]].
-The use of the [[Bischler–Napieralski reaction|Bischler–Napieralski cyclodehydration]] of phenylacetamides of arylethylamines constitutes one of the standard methods for synthesis dihydroisoquinolines; the reaction interestingly works well when the benzene ring in the cyclization is replaced by cyclohexane. Thus reaction with [[polyphosphoric acid]] or POCl<sub>3</sub> gives the hexahydroisoquinoline via the enol form of the amide.
-Exposure to [[sodium borohydride]] or hydrogenation over [[Raney nickel]] leads to selective reduction of the imine bond and formation of the morphinan precursor.
-There are two ways to proceed with the next stage:
-(1): Treatment with strong acid leads proceeds to the morphinan. Acylation with [[ethyl chloroformate]] followed by reduction of the intermediate [[urethane]] leads to Methorphan. Cleavage of the methyl ether then leads to racemorphan.
-(2): The 2° amine is ''N''-methylated by treatment with paraform and reduction over Raney-nickel. The cyclization and O-demethylation step is performed [[concomitantly]] with polyphosphoric acid.
 ==See also==
@@ Line 61: / Line 55: @@
 * [[Methorphan]]
 * [[Morphinan]]
+* [[Cyclorphan]]
+== See also ==
+* [[Cough syrup]]
+* [[Noscapine]]
+* [[Codeine]]; [[Pholcodine]]
+* [[Dextromethorphan]]; [[Dimemorfan]]
+* [[Dextrorphan]]; [[Levorphanol]]
+* [[Butamirate]]
+* [[Pentoxyverine]]
+* [[Tipepidine]]
+* [[Cloperastine]]
+* [[Levocloperastine]]
 ==References==
@@ Line 66: / Line 73: @@
 {{Hallucinogens}}
+{{Navboxes
-{{Glutamatergics}}
+| title = [[Pharmacodynamics]]
-{{Opioidergics}}
+| titlestyle = background:#ccccff
-{{Sigmaergics}}
+| list1 =
+{{Glycine receptor modulators}}
+{{Ion channel modulators}}
+{{Ionotropic glutamate receptor modulators}}
+{{Monoamine reuptake inhibitors}}
+{{Nicotinic acetylcholine receptor modulators}}
+{{Opioid receptor modulators}}
+{{Sigma receptor modulators}}
+}}
 [[Category:Morphinans]]
@@ Line 76: / Line 92: @@
 [[Category:NMDA receptor antagonists]]
 [[Category:Nicotinic antagonists]]
-[[Category:Mu-opioid agonists]]
+[[Category:Mu-opioid receptor agonists]]
-[[Category:Serotonin-norepinephrine reuptake inhibitors]]
+[[Category:Serotonin–norepinephrine reuptake inhibitors]]
 [[Category:Sigma agonists]]
 [[Category:Calcium channel blockers]]
+[[Category:Dissociative drugs]]