Doxpicomine

Doxpicomine

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	℞ (Prescription only)
Identifiers
IUPAC name 1-(1,3-dioxan-5-yl)-N,N-dimethyl-1-pyridin-3-ylmethanamine
CAS Number	69494-04-8
PubChem (CID)	?
ChemSpider	64983
UNII	9821373UA1
KEGG	D03900
Chemical and physical data
Formula	C12H18N2O2
Molar mass	222.283 g/mol
3D model (Jmol)	Interactive image
SMILES CN(C)C(C1COCOC1)C2=CN=CC=C2
InChI InChI=1S/C12H18N2O2/c1-14(2)12(10-4-3-5-13-6-10)11-7-15-9-16-8-11/h3-6,11-12H,7-9H2,1-2H3 Key:SMZVRZPJXBGNFT-UHFFFAOYSA-N
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Doxpicomine (Doxpicodin, Doxpizodine) is a mild opioid analgesic drug.^[1] The drug acts as a mu-opioid receptor agonist.^[2] It is of fairly low potency, with a 400 mg dose of doxpicomine approximately equivalent in pain-killing effect to 8 mg morphine or 100 mg pethidine.^[3][4] It has been used as a lead compound to derive further analogues, although all compounds in this family are comparatively weak mu agonists.^[5]

References

1. US patent 3905987, Booher, R. N., "m-Dioxane-5-Methylamine Analgesics", issued 09/16/1975, assigned to Eli Lilly 
2. Smits, S. E.; Nickander, R.; Booher, R. N.; Zimmerman, D. M.; Wong, D. T.; Hynes, M. D.; Pohland, A. (1981). "Preclinical pharmacology of doxpicodin, a new analgesic". NIDA Research Monograph. 34: 75–81. PMID 6261137.
3. Wang, R. I.; Robinson, N. (1981). "Doxpicomine in postoperative pain". Clinical Pharmacology and Therapeutics. 29 (6): 771–775. doi:10.1038/clpt.1981.109. PMID 7014073.
4. Wang, R. I.; Robinson, N. (1983). "Further efficacy evaluation of doxpicomine for postoperative pain". Journal of Clinical Pharmacology. 23 (1): 44–47. doi:10.1002/j.1552-4604.1983.tb02703.x. PMID 6341416.
5. Wünsch, B.; Bauschke, G. (1993). "Benzomorphan analogs with doxpicomine partial structure: Synthesis andpsychopharmacologic investigations of 5-aminomethyl- and 5-(alpha-aminobenzyl)- substituted 2,6-epoxy-3-benzoxocines" [Benzomorphan analogs with doxpicomine partial structure: synthesis and psychopharmacologic investigations of 5-aminomethyl- and 5-(alpha-aminobenzyl)- substituted 2,6-epoxy-3-benzoxocines]. Archiv der Pharmazie (in German). 326 (3): 171–180. doi:10.1002/ardp.19933260311. PMID 8481096.