Methorphan

Methorphan comes in two isomeric forms, each with differing pharmacology and effects:

Racemethorphan
Levomethorphan (L), dextromethorphan (R)
Clinical data
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • 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
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
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)

Racemethorphan refers to the racemic mixture of both of these stereoisomers.[1] 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.[2][3] The salts in use are the hydrobromide (free base conversion ratio 0.770) and the tartrate (0.644)

See also

References
  1. 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.
  2. "Conversion Factors for Controlled Substances". www.deadiversion.usdoj.gov.
  3. 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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