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.

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[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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v t e Dissociatives
Arylcyclo‐ hexylamines	Ketamine-related: 2-Bromodeschloroketamine (2-BDCK; bromoketamine) 2-Fluorodeschloroketamine (2-FDCK) 2-FXPr 3-Fluorodeschloroketamine (3-FDCK) A-NK Arketamine ((R)-ketamine) Blixeprodil (GM-1020; (R)-4-FDCK) Deoxymethoxetamine (DMXE) Deschloroketamine (DXE, DCK) Ethketamine (N-ethylnorketamine, NENK) Esketamine ((S)-ketamine) Fluorexetamine (3-FXE) Hydroxetamine (HXE) Ketamine (K) Methoxetamine (MXE) Methoxmetamine (MXM, MXME) Methoxypropamine (MXPr) Methoxyketamine Methoxisopropamine (MXiPr) Norketamine (NK) SN-35210 TFMDCK Tiletamine Tilmetamine XW10508 PCP-related: 2-Oxo-PCE 3-Chloro-PCP 3-Fluoro-PCP 3-HO-PCP 3-HO-PCE 3-Me-PCE 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 3-Methyl-PCP 3-Methyl-PCPy 4-Keto-PCP 4-MeO-PCP BDPC Dieticyclidine (PCDE) Eticyclidine (PCE) MDPCP PCPEP PCPr Phencyclidine (PCP) Rolicyclidine (PCPy) TCTHP Tenocyclidine (TCP) Others: Gacyclidine
Diarylethylamines	Diphenidine (1,2-DEP, DPD) Ephenidine (NEDPA, EPE) Fluorolintane (2-FPPP) Methoxphenidine (MXP) NPDPA (isopropylphenidine, isophenidine) Remacemide
Morphinans	Dextrallorphan (DXA) Dextromethorphan (DXM) Dextrorphan (DXO) Racemethorphan (methorphan) Racemorphan (morphanol)
Inhalants	Aliphatic hydrocarbons Butane Gasoline Kerosene Propane Ethers Diethyl ether Enflurane Isoflurane Haloalkanes Chlorofluorocarbons Chloroform Nitrous oxide (N₂O) Xenon (Xe)
Others	2-MDP (U-23807A) 8A-PDHQ Adamantanes (e.g., amantadine, memantine) Alkyl nitrites/poppers (e.g., amyl nitrite) Aptiganel (Cerestat; CNS-1102) CNS-5161 Delucemine Dexoxadrol Dizocilpine (MK-801) Etoxadrol F-17475 Midafotel (CPPene) NEFA Neramexane PD-137889 Perzinfotel Selfotel (CGS-19755)
See also: Hallucinogens Ionotropic glutamate receptor modulators List of hallucinogens

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See also

References