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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number524-84-5
WeightAverage: 263.421
Monoisotopic: 263.080240929
Chemical FormulaC14H17NS2
InChI KeyCANBGVXYBPOLRR-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as heteroaromatic compounds. These are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Thiophene
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Dimethylthiambutene Action PathwayDrug actionSMP00680
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9885
Blood Brain Barrier+0.9151
Caco-2 permeable+0.5906
P-glycoprotein substrateNon-substrate0.6598
P-glycoprotein inhibitor INon-inhibitor0.5836
P-glycoprotein inhibitor IINon-inhibitor0.922
Renal organic cation transporterNon-inhibitor0.7987
CYP450 2C9 substrateNon-substrate0.75
CYP450 2D6 substrateNon-substrate0.7903
CYP450 3A4 substrateNon-substrate0.5436
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 substrateNon-inhibitor0.6854
CYP450 2D6 substrateNon-inhibitor0.7775
CYP450 2C19 substrateNon-inhibitor0.6561
CYP450 3A4 substrateNon-inhibitor0.9009
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.737
Ames testNon AMES toxic0.7154
CarcinogenicityNon-carcinogens0.6805
BiodegradationNot ready biodegradable0.9496
Rat acute toxicity2.7284 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9696
hERG inhibition (predictor II)Non-inhibitor0.8824
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 Solubility0.0839 mg/mLALOGPS
logP4.06ALOGPS
logP4.2ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)8.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity86.67 m3·mol-1ChemAxon
Polarizability29.46 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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

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