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359-83-1 molecular structure
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(1R,9R,13R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-4-ol

ChemBase ID: 534
Molecular Formular: C19H27NO
Molecular Mass: 285.42378
Monoisotopic Mass: 285.20926449
SMILES and InChIs

SMILES:
[C@@]12(c3cc(ccc3C[C@H]([C@@H]1C)N(CC2)CC=C(C)C)O)C
Canonical SMILES:
CC(=CCN1CC[C@@]2([C@H]([C@H]1Cc1c2cc(cc1)O)C)C)C
InChI:
InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m0/s1
InChIKey:
VOKSWYLNZZRQPF-GDIGMMSISA-N

Cite this record

CBID:534 http://www.chembase.cn/molecule-534.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,9R,13R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-4-ol
IUPAC Traditional name
pentazocine
Brand Name
Fortalgesic
Fortalin
Fortral
Liticon
Pentagin
Soseton
Sosigon
Talwan
Synonyms
L-pentazocine
Pentazocaine
Pentazocin
Pentazocine
CAS Number
359-83-1
PubChem SID
160963997
46506363
PubChem CID
441278

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 10.421619  H Acceptors
H Donor LogD (pH = 5.5) 0.8584462 
LogD (pH = 7.4) 1.9896134  Log P 3.89362 
Molar Refractivity 89.7993 cm3 Polarizability 34.580894 Å3
Polar Surface Area 23.47 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.44  LOG S -3.37 
Solubility (Water) 1.22e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
3.7 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00652 external link
Item Information
Drug Groups approved
Description The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)
Indication For the relief of moderate to severe pain.
Pharmacology Pentazocine is a potent analgesic which when administered orally in a 50 mg dose appears equivalent in analgesic effect to 60 mg (1 grain) of codeine. Onset of significant analgesia usually occurs between 15 and 30 minutes after oral administration, and duration of action is usually three hours or longer. Onset and duration of action and the degree of pain relief are related both to dose and the severity of pretreatment pain. Pentazocine weakly antagonizes the analgesic effects of morphine and meperidine; in addition, it produces incomplete reversal of cardiovascular, respiratory, and behavioral depression induced by morphine and meperidine. Pentazocine has about 1/50 the antagonistic activity of nalorphine. It also has sedative activity.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Well absorbed from the gastro-intestinal tract.
Half Life 2 to 3 hours
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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