Home > Compound List > Compound details
125-28-0 molecular structure
click picture or here to close

(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-ol

ChemBase ID: 1336
Molecular Formular: C18H23NO3
Molecular Mass: 301.38012
Monoisotopic Mass: 301.1677936
SMILES and InChIs

SMILES:
O1[C@@H]2[C@]34[C@H]([C@H](N(CC3)C)Cc3c4c1c(OC)cc3)CC[C@@H]2O
Canonical SMILES:
COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4CC[C@@H]1O)C
InChI:
InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChIKey:
RBOXVHNMENFORY-DNJOTXNNSA-N

Cite this record

CBID:1336 http://www.chembase.cn/molecule-1336.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-ol
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-ol
IUPAC Traditional name
dihydrocodeine
Synonyms
Dihydrocodeine
CAS Number
125-28-0
PubChem SID
160964796
46506478
PubChem CID
5284543
ATC CODE
N02AA08
CHEMBL
1595
Chemspider ID
4447600
DrugBank ID
DB01551
KEGG ID
D07831
Unique Ingredient Identifier
N9I9HDB855
Wikipedia Title
Dihydrocodeine

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.151551  H Acceptors
H Donor LogD (pH = 5.5) -1.7857474 
LogD (pH = 7.4) -0.3756574  Log P 1.5489655 
Molar Refractivity 83.6421 cm3 Polarizability 32.852997 Å3
Polar Surface Area 41.93 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.58  LOG S -2.1 
Solubility (Water) 2.38e+00 g/l 

PROPERTIES

PROPERTIES

Pharmacology Properties Bioassay(PubChem)
Admin Routes
Oral, subcutaneous, I.M., rectal, possiblly sublingual/buccal expand Show data source
Bioavailability
20% expand Show data source
Half Life
4 hours expand Show data source
Metabolism
Mainly hepatic, through CYP3A4 and CYP2D6 expand Show data source
Legal Status
Class B (UK) expand Show data source
S2, S3, S4 depending on dose and other constituents (Australia) expand Show data source
Schedule II (US) expand Show data source
Pregnancy Category
C (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB01551 external link
Item Information
Drug Groups illicit; experimental
References
Rowell FJ, Seymour RA, Rawlins MD: Pharmacokinetics of intravenous and oral dihydrocodeine and its acid metabolites. Eur J Clin Pharmacol. 1983;25(3):419-24. [Pubmed]
Schmidt H, Vormfelde SV, Walchner-Bonjean M, Klinder K, Freudenthaler S, Gleiter CH, Gundert-Remy U, Skopp G, Aderjan R, Fuhr U: The role of active metabolites in dihydrocodeine effects. Int J Clin Pharmacol Ther. 2003 Mar;41(3):95-106. [Pubmed]
O'Neill WM, Hanks GW, Simpson P, Fallon MT, Jenkins E, Wesnes K: The cognitive and psychomotor effects of morphine in healthy subjects: a randomized controlled trial of repeated (four) oral doses of dextropropoxyphene, morphine, lorazepam and placebo. Pain. 2000 Mar;85(1-2):209-15. [Pubmed]
External Links
Wikipedia

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Rowell FJ, Seymour RA, Rawlins MD: Pharmacokinetics of intravenous and oral dihydrocodeine and its acid metabolites. Eur J Clin Pharmacol. 1983;25(3):419-24. Pubmed
  • • Schmidt H, Vormfelde SV, Walchner-Bonjean M, Klinder K, Freudenthaler S, Gleiter CH, Gundert-Remy U, Skopp G, Aderjan R, Fuhr U: The role of active metabolites in dihydrocodeine effects. Int J Clin Pharmacol Ther. 2003 Mar;41(3):95-106. Pubmed
  • • O'Neill WM, Hanks GW, Simpson P, Fallon MT, Jenkins E, Wesnes K: The cognitive and psychomotor effects of morphine in healthy subjects: a randomized controlled trial of repeated (four) oral doses of dextropropoxyphene, morphine, lorazepam and placebo. Pain. 2000 Mar;85(1-2):209-15. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle