Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameDimethylthiambutene
Accession NumberDB01444
Typesmall molecule
Groupsexperimental, illicit
Description

Dimethylthiambutene (N,N-Dimethyl-1-methyl-3,3-di-2-thienylallylamine, Dimethibutin, Ohton) is an opioid analgesic drug. It is now under international control under Schedule I of the UN Single Convention On Narcotic Drugs 1961, presumably due to high abuse potential, although little more information is available.

Structure
Thumb
Synonyms
SynonymLanguageCode
DimethibutinNot AvailableNot Available
OhtonNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number524-84-5
WeightAverage: 263.421
Monoisotopic: 263.080240929
Chemical FormulaC14H17NS2
InChI KeyInChIKey=CANBGVXYBPOLRR-UHFFFAOYSA-N
InChI
InChI=1S/C14H17NS2/c1-11(15(2)3)10-12(13-6-4-8-16-13)14-7-5-9-17-14/h4-11H,1-3H3
IUPAC Name
[4,4-bis(thiophen-2-yl)but-3-en-2-yl]dimethylamine
SMILES
CC(C=C(C1=CC=CS1)C1=CC=CS1)N(C)C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassThiophenes
SubclassNot Available
Direct parentThiophenes
Alternative parentsTertiary Amines; Polyamines
Substituentstertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the thiophenes. These are compounds containing a five-member aromatic compound made up of one sulfur atom and four carbon atoms.
Pharmacology
IndicationDimethylthiambutene is an opioid analgesic previously used in moderate pain relief.
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9885
Blood Brain Barrier + 0.9151
Caco-2 permeable + 0.5906
P-glycoprotein substrate Non-substrate 0.6598
P-glycoprotein inhibitor I Non-inhibitor 0.5836
P-glycoprotein inhibitor II Non-inhibitor 0.922
Renal organic cation transporter Non-inhibitor 0.7987
CYP450 2C9 substrate Non-substrate 0.75
CYP450 2D6 substrate Non-substrate 0.7903
CYP450 3A4 substrate Non-substrate 0.5436
CYP450 1A2 substrate Non-inhibitor 0.5
CYP450 2C9 substrate Non-inhibitor 0.6854
CYP450 2D6 substrate Non-inhibitor 0.7775
CYP450 2C19 substrate Non-inhibitor 0.6561
CYP450 3A4 substrate Non-inhibitor 0.9009
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.737
Ames test Non AMES toxic 0.7154
Carcinogenicity Non-carcinogens 0.6805
Biodegradation Not ready biodegradable 0.9496
Rat acute toxicity 2.7284 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9696
hERG inhibition (predictor II) Non-inhibitor 0.8824
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point157.5 °C at 3.00E+00 mm HgPhysProp
Predicted Properties
PropertyValueSource
water solubility8.39e-02 g/lALOGPS
logP4.06ALOGPS
logP4.2ChemAxon
logS-3.5ALOGPS
pKa (strongest basic)8.67ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area3.24ChemAxon
rotatable bond count4ChemAxon
refractivity86.67ChemAxon
polarizability29.46ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound10668
PubChem Substance46505069
ChemSpider10218
ChEBI59781
ChEMBL
WikipediaDimethylthiambutene
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. GREEN AF: Comparative effects of analgesics on pain threshold, respiratory frequency and gastrointestinal propulsion. Br J Pharmacol Chemother. 1959 Mar;14(1):26-34. Pubmed

2. Delta-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Delta-type opioid receptor P41143 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Comments
Drug created on July 31, 2007 07:09 / Updated on September 16, 2013 17:14