Racemorphan

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

Legal status

• AU: S9 (Prohibited substance)
• BR: Class A1 (Narcotic drugs)^[1]
• CA: Schedule I
• DE: Anlage II (Authorized trade only, not prescriptible)
• UK: Class A
• US: Schedule II
• UN: Psychotropic Schedule I

CAS Number

• 297-90-5
  5985-35-3 (HBr)

PubChem CID

• 3918

ChemSpider

• 3781

Quick facts Legal status, Identifiers ...

Racemorphan

Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs)[1] 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
ECHA InfoCard	100.005.499
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

Close

Its analgesic activity is intermediate between Dextrorphan and Levorphanol.^[2]

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.^[3] The salts in use are hydrobromide (free base conversion ratio 0.741), hydrochloride (0.876), and tartrate (0.632).