Identification

Name
Methadyl acetate
Accession Number
DB01433
Type
Small Molecule
Groups
Experimental, Illicit
Description

A narcotic analgesic with a long onset and duration of action. It is used mainly in the treatment of narcotic dependence.

Structure
Thumb
Synonyms
  • Acetilmetadol
  • Acetylmethadol
  • Acetylmethadolum
External IDs
ACSCN-9601 / IDS-NA-004 / NIH-2953
Product Ingredients
IngredientUNIICASInChI Key
Methadyl acetate hydrochloride3ZD9WAO92T38821-43-1UXBPQRGCVJOTNT-UHFFFAOYSA-N
Categories
UNII
L59OC40KWJ
CAS number
509-74-0
Weight
Average: 353.4977
Monoisotopic: 353.235479241
Chemical Formula
C23H31NO2
InChI Key
XBMIVRRWGCYBTQ-UHFFFAOYSA-N
InChI
InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3
IUPAC Name
6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate
SMILES
CCC(OC(C)=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

Used mainly in the treatment of narcotic dependence.

Pharmacodynamics

Methadyl Acetate is a narcotic analgesic with a long onset and duration of action. The drug decreases a patients opioid use by preventing opioid withdrawal and in how it can mimic some of the effects of opioids.

Mechanism of action

Methadyl Acetate is primarily a mu-type opioid receptor agonist. It functions similarily to methadone.

TargetActionsOrganism
AMu-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
Methadyl Acetate Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Methadyl acetate is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Methadyl acetate is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Methadyl acetate is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Methadyl acetate is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Methadyl acetate is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Methadyl acetate is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Methadyl acetate is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when Methadyl acetate is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of hypotension and central nervous system depression can be increased when Acepromazine is combined with Methadyl acetate.
AceprometazineThe risk or severity of hypotension and central nervous system depression can be increased when Aceprometazine is combined with Methadyl acetate.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015502
PubChem Compound
10517
PubChem Substance
46505532
ChemSpider
10080
BindingDB
50027391
ChEBI
135491
ChEMBL
CHEMBL170179
Therapeutic Targets Database
DAP001137
PharmGKB
PA164746889
Wikipedia
Acetylmethadol

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
Solid
Experimental Properties
PropertyValueSource
logP4.27HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00179 mg/mLALOGPS
logP4.78ALOGPS
logP4.88ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)9.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.86 m3·mol-1ChemAxon
Polarizability40.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9965
Blood Brain Barrier+0.9648
Caco-2 permeable+0.7459
P-glycoprotein substrateSubstrate0.5822
P-glycoprotein inhibitor IInhibitor0.8472
P-glycoprotein inhibitor IINon-inhibitor0.8897
Renal organic cation transporterNon-inhibitor0.6473
CYP450 2C9 substrateNon-substrate0.7976
CYP450 2D6 substrateNon-substrate0.8641
CYP450 3A4 substrateSubstrate0.6658
CYP450 1A2 substrateInhibitor0.5619
CYP450 2C9 inhibitorNon-inhibitor0.8153
CYP450 2D6 inhibitorInhibitor0.7123
CYP450 2C19 inhibitorNon-inhibitor0.7312
CYP450 3A4 inhibitorInhibitor0.5242
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5811
Ames testNon AMES toxic0.9016
CarcinogenicityCarcinogens 0.7025
BiodegradationNot ready biodegradable0.9792
Rat acute toxicity3.3406 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9706
hERG inhibition (predictor II)Inhibitor0.7157
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 diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Aralkylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Diphenylmethane / Aralkylamine / Amino acid or derivatives / Carboxylic acid ester / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid derivative / Monocarboxylic acid or derivatives / Amine / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

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. Mancino MJ, McGaugh J, Feldman Z, Poling J, Oliveto A: Effect of PTSD diagnosis and contingency management procedures on cocaine use in dually cocaine- and opioid-dependent individuals maintained on LAAM: a retrospective analysis. Am J Addict. 2010 Mar-Apr;19(2):169-77. doi: 10.1111/j.1521-0391.2009.00025.x. [PubMed:20163389]
  2. Walczak SA, Makman MH, Gardner EL: Acetylmethadol metabolites influence opiate receptors and adenylate cyclase in amygdala. Eur J Pharmacol. 1981 Jul 10;72(4):343-9. [PubMed:6268422]
  3. Wolstein J, Gastpar M, Finkbeiner T, Heinrich C, Heitkamp R, Poehlke T, Scherbaum N: A randomized, open-label trial comparing methadone and Levo-Alpha-Acetylmethadol (LAAM) in maintenance treatment of opioid addiction. Pharmacopsychiatry. 2009 Jan;42(1):1-8. doi: 10.1055/s-0028-1083818. Epub 2009 Jan 19. [PubMed:19153939]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on July 24, 2007 14:16 / Updated on November 02, 2018 09:06