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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H18N2O2.ClH
Molecular Weight 258.744
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXPICOMINE HYDROCHLORIDE

SMILES

Cl.CN(C)[C@H](C1COCOC1)C2=CC=CN=C2

InChI

InChIKey=LCQSIRUFGUHZQH-YDALLXLXSA-N
InChI=1S/C12H18N2O2.ClH/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;1H/t12-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C12H18N2O2
Molecular Weight 222.2835
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Doxpicomine is the hydrochloride salt of l-3[(dimethylamino)-(m-dioxan-5-yl)methyl]pyridine, a derivative of substituted 1,3 dioxanes. Its analgesic effect appears to be mediated centrally through opiate-like receptors. Preclinical animal studies revealed analgesic activity and duration of action of the same order as that of meperidine and codeine when administered subcutaneously and of codeine but of shorter duration when administered orally. The analgesic effects were reversed by naloxone. The drug did not reduce or antagonize the analgesic effect of morphine. Drowsiness is an expected response to effective analgesics. It was the foremost side effect observed but was of short duration and minimal intensity and did not interfere with the postoperative regimen of coughing, deep breathing, and early ambulation. Nausea and vomiting were not reported after doxpicomine.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Benzomorphan analogs with doxpicomine partial structure: synthesis andpsychopharmacologic investigations of 5-aminomethyl- and 5-(alpha-aminobenzyl)- substituted 2,6-epoxy-3-benzoxocines].
1993-03
Further efficacy evaluation of doxpicomine for postoperative pain.
1983-01
Doxpicomine in postoperative pain.
1981-06
Preclinical pharmacology of doxpicodin, a new analgesic.
1981-02
The disposition of l-3-[(dimethylamino)-(m-dioxan-5-yl)methyl]pyridine in man.
1979-05-01

Sample Use Guides

Single dose - 400 mg
Route of Administration: Intramuscular
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:53:57 GMT 2025
Edited
by admin
on Mon Mar 31 17:53:57 GMT 2025
Record UNII
27DYG0QPCR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOXPICOMINE HYDROCHLORIDE
USAN  
USAN  
Official Name English
LY 108380
Preferred Name English
LY-108380
Code English
NSC-332377
Code English
(R)-(.ALPHA.-(1,3-DIOXAN-5-YL)-N,N-DIMETHYL-3-PYRIDINEMETHANAMINE HYDROCHLORIDE
Common Name English
3-PYRIDINEMETHANAMINE, .ALPHA.-1,3-DIOXAN-5-YL-N,N-DIMETHYL-, MONOHYDROCHLORIDE, (-)-
Common Name English
DOXPICOMINE HCL
Common Name English
(-)-3-((DIMETHYLAMINO)-M-DIOXAN-5-YLMETHYL)PYRIDINE MONOHYDROCHLORIDE
Systematic Name English
DOXPICOMINE HYDROCHLORIDE [USAN]
Common Name English
3-PYRIDINEMETHANAMINE, .ALPHA.-1,3-DIOXAN-5-YL-N,N-DIMETHYL-, MONOHYDROCHLORIDE, (.ALPHA.R)-
Common Name English
DOXPICODIN HYDROCHLORIDE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID301024450
Created by admin on Mon Mar 31 17:53:57 GMT 2025 , Edited by admin on Mon Mar 31 17:53:57 GMT 2025
PRIMARY
CAS
69494-04-8
Created by admin on Mon Mar 31 17:53:57 GMT 2025 , Edited by admin on Mon Mar 31 17:53:57 GMT 2025
PRIMARY
NSC
332377
Created by admin on Mon Mar 31 17:53:57 GMT 2025 , Edited by admin on Mon Mar 31 17:53:57 GMT 2025
PRIMARY
ChEMBL
CHEMBL2110861
Created by admin on Mon Mar 31 17:53:57 GMT 2025 , Edited by admin on Mon Mar 31 17:53:57 GMT 2025
PRIMARY
NCI_THESAURUS
C166550
Created by admin on Mon Mar 31 17:53:57 GMT 2025 , Edited by admin on Mon Mar 31 17:53:57 GMT 2025
PRIMARY
FDA UNII
27DYG0QPCR
Created by admin on Mon Mar 31 17:53:57 GMT 2025 , Edited by admin on Mon Mar 31 17:53:57 GMT 2025
PRIMARY
SMS_ID
300000055437
Created by admin on Mon Mar 31 17:53:57 GMT 2025 , Edited by admin on Mon Mar 31 17:53:57 GMT 2025
PRIMARY
PUBCHEM
76967288
Created by admin on Mon Mar 31 17:53:57 GMT 2025 , Edited by admin on Mon Mar 31 17:53:57 GMT 2025
PRIMARY
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