Chemistry:Methorphan

Short description: Group of stereoisomers

Racemethorphan

Levomethorphan (L), dextromethorphan (R)
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
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 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. 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. The salts in use are the hydrobromide (free base conversion ratio 0.770) and the tartrate (0.644)

See also

• Morphinan
• Racemorphan