Doxpicomine

Doxpicomine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 1-(1,3-dioxan-5-yl)-N,N-dimethyl-1-pyridin-3-ylmethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC12H18N2O2
Molar mass222.288 g·mol−1
3D model (JSmol)
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 ☒N
  • Key:SMZVRZPJXBGNFT-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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 RN, "m-Dioxane-5-Methylamine Analgesics", issued 09/16/1975, assigned to Eli Lilly
  2. ↑ Smits SE, Nickander R, Booher RN, Zimmerman DM, Wong DT, Hynes MD, Pohland A (February 1981). "Preclinical pharmacology of doxpicodin, a new analgesic". NIDA Research Monograph. 34: 75–81. PMID 6261137.
  3. ↑ Wang RI, Robinson N (June 1981). "Doxpicomine in postoperative pain". Clinical Pharmacology and Therapeutics. 29 (6): 771–5. doi:10.1038/clpt.1981.109. PMID 7014073. S2CID 24849960.
  4. ↑ Wang RI, Robinson N (January 1983). "Further efficacy evaluation of doxpicomine for postoperative pain". Journal of Clinical Pharmacology. 23 (1): 44–7. doi:10.1002/j.1552-4604.1983.tb02703.x. PMID 6341416. S2CID 36306783.
  5. ↑ Wünsch B, Bauschke G (March 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): 171–80. doi:10.1002/ardp.19933260311. PMID 8481096. S2CID 98749966.
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