Methorphan

Racemethorphan
Clinical data
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule II; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name 3-Methoxy-17-methylmorphinan;
CAS Number	510-53-2 ;
PubChem CID	3008;
ChemSpider	2901 ;
UNII	8YB8F78WM1;
ChEBI	CHEBI:146177;
ChEMBL	ChEMBL22207 ;
CompTox Dashboard (EPA)	DTXSID60859238 ;
Chemical and physical data
Formula	C18H25NO
Molar mass	271.404 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC;
	InChI InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3 ; Key:MKXZASYAUGDDCJ-UHFFFAOYSA-N ;
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Methorphan comes in two isomeric forms, each with differing pharmacology and effects:

Dextromethorphan – An over-the-counter cough suppressant, as well as dissociative hallucinogen.
Levomethorphan – A potent opioid analgesic that was never clinically developed; a prodrug of the powerful opioid agonist analgesic levorphanol (Levo-Dromoran).

Racemethorphan is the racemic mixture of both of these stereoisomers!^[2] It is listed under the Single Convention on Narcotic Drugs 1961 and is therefore listed in the United States as a Controlled Substance, specifically as a Narcotic in Schedule II with an ACSCN of 9732 and an annual aggregate manufacturing quota of 3 grams in 2014.^[3]^[4] The salts in use are the hydrobromide (free base conversion ratio 0.770) and the tartrate (0.644).

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.
^ Aumatell A, Wells RJ (December 1993). "Chiral differentiation of the optical isomers of racemethorphan and racemorphan in urine by capillary zone electrophoresis". Journal of Chromatographic Science. 31 (12): 502–8. doi:10.1093/chromsci/31.12.502. PMID 8120122.
^ "Conversion Factors for Controlled Substances". www.deadiversion.usdoj.gov.
^ Nordegren T (2002). "Racemethorphan". The A-Z Encyclopedia of Alcohol and Drug Abuse. Parkland, Fla.: Brown Walker Press. pp. 548–549. ISBN 978-1-58112-404-0.

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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.

[Aumatell_1993-2] Aumatell A, Wells RJ (December 1993). "Chiral differentiation of the optical isomers of racemethorphan and racemorphan in urine by capillary zone electrophoresis". Journal of Chromatographic Science. 31 (12): 502–8. doi:10.1093/chromsci/31.12.502. PMID 8120122.

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

[4] Nordegren T (2002). "Racemethorphan". The A-Z Encyclopedia of Alcohol and Drug Abuse. Parkland, Fla.: Brown Walker Press. pp. 548–549. ISBN 978-1-58112-404-0.

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Methorphan

See also

References

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