Identification

Name
Dimethylthiambutene
Accession Number
DB01444
Type
Small Molecule
Groups
Experimental, 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
  • Dimethibutin
  • Ohton
Categories
Not Available
UNII
915D88LM9O
CAS number
524-84-5
Weight
Average: 263.421
Monoisotopic: 263.080240929
Chemical Formula
C14H17NS2
InChI Key
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

Pharmacology

Indication

Dimethylthiambutene is an opioid analgesic previously used in moderate pain relief.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AMu-type opioid receptor
agonist
Human
UDelta-type opioid receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Dimethylthiambutene Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB61719
PubChem Compound
10668
PubChem Substance
46505069
ChemSpider
10218
ChEBI
59781
ChEMBL
CHEMBL2106265
Wikipedia
Dimethylthiambutene

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)157.5 °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 RuleNoChemAxon
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 inhibitorNon-inhibitor0.6854
CYP450 2D6 inhibitorNon-inhibitor0.7775
CYP450 2C19 inhibitorNon-inhibitor0.6561
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Heteroaromatic compounds
Sub Class
Not Available
Direct Parent
Heteroaromatic compounds
Alternative Parents
Thiophenes / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Heteroaromatic compound / Thiophene / Tertiary aliphatic amine / Tertiary amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Amine / Aromatic heteromonocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary amine, thiophenes (CHEBI:59781)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
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:17139284]
  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:17016423]
  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:13651575]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
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:17139284]
  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:17016423]

Drug created on July 31, 2007 07:09 / Updated on November 09, 2017 03:00