Chemistry:Racemorphan

Short description: Racemic mixture

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
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

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. The salts in use are hydrobromide (free base conversion ratio 0.741), hydrochloride (0.876), and tartrate (0.632).

See also

• Levallorphan
• Methorphan
• Morphinan
• Cyclorphan

See also

• Cough syrup
• Noscapine
• Codeine; Pholcodine
• Dextromethorphan; Dimemorfan
• Dextrorphan; Levorphanol
• Butamirate
• Pentoxyverine
• Tipepidine
• Cloperastine
• Levocloperastine