ContaminantDB: Methadone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2009-07-15 20:47:26 UTC

Update Date

2026-03-26 18:30:48 UTC

Accession Number

CHEM002121

Identification

Common Name

Methadone

Class

Small Molecule

Description

A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of morphine. It also has a depressant action on the cough center and may be given to control intractable cough associated with terminal lung cancer. Methadone is also used as part of the treatment of dependence on opioid drugs, although prolonged use of methadone itself may result in dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3). In Australia methadone is a Schedule 8 (controlled) drug.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds
Suspected Compounds - Waste Water
T3DB toxins

Contaminant Type

Amine
Analgesic
Analgesic, Opioid
Antitussive Agent
Drug
Metabolite
Narcotic
Opiate Agonist
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-(Dimethylamino)-4,4-diphenyl-3-heptanone	ChEBI
(+-)-Methadone	ChEBI
6-dimethylamino-4,4-Diphenyl-3-heptanone	ChEBI
DL-Methadone	ChEBI
Methadonum	ChEBI
(+/-)-methadone	HMDB
(+/-)-methadone hydrochloride	HMDB
DL-Methadone hydrochloride	HMDB
Methadon	HMDB
Methadone HCL	HMDB
Methadone hydrochloride	HMDB
Phenadone hydrochloride	HMDB
Amidone	MeSH, HMDB
Biomet brand OF methadone hydrochloride	MeSH, HMDB
Methadose	MeSH, HMDB
Yamanouchi brand OF methadone hydrochloride	MeSH, HMDB
AddiCare brand OF methadone hydrochloride	MeSH, HMDB
Dolophine	MeSH, HMDB
Generics brand OF methadone hydrochloride	MeSH, HMDB
GlaxoSmithKline brand OF methadone hydrochloride	MeSH, HMDB
Hydrochloride, methadone	MeSH, HMDB
Mallinckrodt brand OF methadone hydrochloride	MeSH, HMDB
Methex	MeSH, HMDB
Pharmascience brand OF methadone hydrochloride	MeSH, HMDB
Phymet	MeSH, HMDB
Physeptone	MeSH, HMDB
Pinadone	MeSH, HMDB
Esteve brand OF methadone hydrochloride	MeSH, HMDB
Metasedin	MeSH, HMDB
Methaddict	MeSH, HMDB
Phenadone	MeSH, HMDB
Rosemont brand OF methadone hydrochloride	MeSH, HMDB
Roxane brand OF methadone hydrochloride	MeSH, HMDB
Symoron	MeSH, HMDB
Biodone	MeSH, HMDB
Martindale brand OF methadone hydrochloride	MeSH, HMDB
Metadol	MeSH, HMDB
Pinewood brand OF methadone hydrochloride	MeSH, HMDB

Chemical Formula

C₂₁H₂₇NO

Average Molecular Mass

309.445 g/mol

Monoisotopic Mass

309.209 g/mol

CAS Registry Number

76-99-3

IUPAC Name

6-(dimethylamino)-4,4-diphenylheptan-3-one

Traditional Name

methadone

SMILES

CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3

InChI Key

USSIQXCVUWKGNF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes 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

Substituents

Diphenylmethane
Aralkylamine
Gamma-aminoketone
Ketone
Tertiary amine
Tertiary aliphatic amine
Carbonyl group
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amine (CHEBI:6807 )
benzenes (CHEBI:6807 )
ketone (CHEBI:6807 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Crystalline powder (MSDS A308)

Experimental Properties

Property	Value
Melting Point	235.0°C
Boiling Point	Not Available
Solubility	5.90e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0059 g/L	ALOGPS
logP	4.14	ALOGPS
logP	5.01	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	18.78	ChemAxon
pKa (Strongest Basic)	9.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.27 m³·mol⁻¹	ChemAxon
Polarizability	36.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9310000000-d71659ee33e210178a79	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-03di-0009000000-c583dd769bf5998ac160	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9310000000-d71659ee33e210178a79	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-03di-0009000000-c583dd769bf5998ac160	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-9080000000-1cd26d01442b30c05512	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0029000000-43d5c8da88c1aa260682	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0090000000-31b8655a24b30962bd8c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01b9-0590000000-9894da52e88d32034318	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0940000000-fedb75bd4c80c6c4fea9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gb9-0940000000-a27b5f75aab7fac8931d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0090000000-1d4283f6dffa11b765e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0019000000-416fca50b212d00b968c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0090000000-ad95925610aed55afe91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0aor-1980000000-6d4d0adc4c8db177eaad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-1920000000-0548504791642aa3b2e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-2920000000-dd2ce03c02a54aa24f83	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-3910000000-1af5f56241eabde05700	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0019000000-015df6e52b9d5ebe5cb2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0091000000-b328f3740a7ca4485324	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0aor-0980000000-24074e0b5c722d7279c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-1920000000-5477eb89abafab290dd1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-2920000000-b4ffdf7888e464422c0c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-3910000000-6053da2e4586dbcae300	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0090000000-0863c3130ca5df5f25b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0069000000-144e893c575a6cb0ceb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-8093000000-72ef33a6770239211ec3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aw9-9780000000-930cd0f8dcbecbc72f1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0019000000-3418a56694229e2c6595	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-3069000000-10bb89e35854fe0680a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fu-9180000000-abf68f949ff2ecf35fcc	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9210000000-7542d8c3f742c7713c13	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (MSDS, RxList, A308); dermal (MSDS, RxList, A308); ingestion (MSDS, RxList, A308); intravenous injection (MSDS, RxList, A308). Well absorbed following oral administration. The bioavailability of methadone ranges between 36 to 100%.

Mechanism of Toxicity

Methadone is a mu-agonist; a synthetic opioid analgesic with multiple actions qualitatively similar to those of morphine, the most prominent of which involves the central nervous system and organs composed of smooth muscle. The principal therapeutic uses for methadone are for analgesia and for detoxification or maintenance in opioid addiction. The methadone abstinence syndrome, although qualitatively similar to that of morphine, differs in that the onset is slower, the course is more prolonged, and the symptoms are less severe. Some data also indicate that methadone acts as an antagonist at the N-methyl-D-aspartate (NMDA) receptor. The contribution of NMDA receptor antagonism to methadone's efficacy is unknown. Other NMDA receptor antagonists have been shown to produce neurotoxic effects in animals.

Metabolism

Hepatic. Cytochrome P450 enzymes, primarily CYP3A4, CYP2B6, and CYP2C19 and to a lesser extent CYP2C9 and CYP2D6, are responsible for conversion of methadone to EDDP and other inactive metabolites, which are excreted mainly in the urine. Route of Elimination: The elimination of methadone is mediated by extensive biotransformation, followed by renal and fecal excretion. Unmetabolized methadone and its metabolites are excreted in urine to a variable degree. Half Life: 24-36 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of dry cough, drug withdrawal syndrome, opioid type drug dependence, and pain (1).

Minimum Risk Level

Not Available

Health Effects

Bradycardia and hypotension. In severe overdosage, particularly by the intravenous route, apnea, circulatory collapse, cardiac arrest, and death may occur (RxList, A308). Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.

Symptoms

In severe overdosage, particularly by the intravenous route, apnea, circulatory collapse, cardiac arrest, and death may occur.

Treatment

Primary attention should be given to the reestablishment of adequate respiratory exchange through provision of a patent airway and institution of assisted or controlled ventilation. If a non-tolerant person, takes a large dose of methadone, effective opioid antagonists are available to counteract the potentially lethal respiratory depression. (10)

Concentrations

Not Available

External Links

DrugBank ID

DB00333

HMDB ID

HMDB0257401

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID