Pseudocodeine

Pseudocodeine
Names
	Systematic IUPAC name (4R,4aR,5S,7aS,12bS)-9-methoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-5-ol
	Other names Neoisocodeine; psi-Codeine;
Identifiers
CAS Number	466-96-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	4588983 ;
ECHA InfoCard	100.006.711
PubChem CID	5486611;
UNII	73786Q1Q4G ;
CompTox Dashboard (EPA)	DTXSID70963618 ;
	InChI InChI=1S/C18H21NO3/c1-19-8-7-18-14-6-4-12(20)16(18)11(19)9-10-3-5-13(21-2)17(22-14)15(10)18/h3-6,11-12,14,16,20H,7-9H2,1-2H3/t11-,12+,14+,16-,18-/m1/s1 Key: KYIVACLUFRUFLS-CVXFFHBFSA-N ;
	SMILES CN1CC[C@]23[C@@H]4C=C[C@@H]([C@H]2[C@H]1CC5=C3C(=C(C=C5)OC)O4)O;
Properties
Chemical formula	C18H21NO3
Molar mass	299.370 g·mol−1
Melting point	180 °C (356 °F; 453 K)
Hazards
	Lethal dose or concentration (LD, LC):
LDLo (lowest published)	1,783 mg kg−1 (subcutaneous, mouse)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pseudocodeine is an isomer of codeine, once studied for its use as an analgesic.^[1]^[2] Like codeine, its neighbouring alkene and alcohol groups allow options for functionalisation.^[3]

References

^ Journal of Pharmacology and Experimental Therapeutics., 55(127), 1935
^ Eddy, Nathan B. (1932). "studies of Morphine, Codeine and Their Derivatives II. Isomers of Codeine". The Journal of Pharmacology and Experimental Therapeutics. 45 (3): 361–381. doi:10.1016/S0022-3565(25)07960-1.
^ Kalinin, V. N.; Kazantseva, S. A.; Kobak, V. V.; Petrovskii, P. V.; Polyakov, A. V.; Yanovskii, A. I.; Struchkov, Yu. T. (1993-03-02). "ChemInform Abstract: Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine. Crystal and Molecular Structure of 8β-Bis( methoxycarbonyl)methyl-8-deoxypseudocodeine". ChemInform. 24 (9) chin.199309232. doi:10.1002/chin.199309232. ISSN 0931-7597.

[1] Journal of Pharmacology and Experimental Therapeutics., 55(127), 1935

[2] Eddy, Nathan B. (1932). "studies of Morphine, Codeine and Their Derivatives II. Isomers of Codeine". The Journal of Pharmacology and Experimental Therapeutics. 45 (3): 361–381. doi:10.1016/S0022-3565(25)07960-1.

[3] Kalinin, V. N.; Kazantseva, S. A.; Kobak, V. V.; Petrovskii, P. V.; Polyakov, A. V.; Yanovskii, A. I.; Struchkov, Yu. T. (1993-03-02). "ChemInform Abstract: Nucleophilic Substitution in the Allylic System of Codeine and Pseudocodeine. Crystal and Molecular Structure of 8β-Bis( methoxycarbonyl)methyl-8-deoxypseudocodeine". ChemInform. 24 (9) chin.199309232. doi:10.1002/chin.199309232. ISSN 0931-7597.

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