Racemorphan

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;
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;

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

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).

References

Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
Benson WM, Stefko PL, Randall LO (October 1953). "Comparative pharmacology of levorphan, racemorphan and dextrorphan and related methyl ethers". The Journal of Pharmacology and Experimental Therapeutics. 109 (2): 189–200. doi:10.1016/S0022-3565(25)05255-3. PMID 13097351.
"Conversion Factors for Controlled Substances". www.deadiversion.usdoj.gov. Archived from the original on 2016-03-02. Retrieved 2016-02-27.

[1] Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[Benson_1953-2] Benson WM, Stefko PL, Randall LO (October 1953). "Comparative pharmacology of levorphan, racemorphan and dextrorphan and related methyl ethers". The Journal of Pharmacology and Experimental Therapeutics. 109 (2): 189–200. doi:10.1016/S0022-3565(25)05255-3. PMID 13097351.

[3] "Conversion Factors for Controlled Substances". www.deadiversion.usdoj.gov. Archived from the original on 2016-03-02. Retrieved 2016-02-27.

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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

See also

References