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 N;
PubChem CID	3008;
ChemSpider	2901 N;
UNII	8YB8F78WM1;
ChEBI	CHEBI:146177;
ChEMBL	ChEMBL22207 N;
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 N; Key:MKXZASYAUGDDCJ-UHFFFAOYSA-N N;
	NY (what is this?) (verify)

Methorphan is an opioid drug that occurs 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 2014.³⁴ The salts in use are the hydrobromide (free base conversion ratio 0.770) and the tartrate (0.644).

References

Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
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. Archived from the original on 2 March 2016. Retrieved 27 February 2016.
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.

[1] Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[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. Archived from the original on 2 March 2016. Retrieved 27 February 2016.

[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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See also

References