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	62904-71-6 ; HCl: 69494-04-8 ;
PubChem CID	71587215;
ChemSpider	64983 ;
UNII	9821373UA1; HCl: 27DYG0QPCR ;
KEGG	D03900 ;
Chemical and physical data
Formula	C12H18N2O2
Molar mass	222.288 g·mol−1
3D model (JSmol)	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 ;
	(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

^ US patent 3905987, Booher RN, "m-Dioxane-5-Methylamine Analgesics", issued 09/16/1975, assigned to Eli Lilly
^ 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.
^ 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.
^ 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.
^ 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.

[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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References

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