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Substance Name: Methadone [INN:BAN]
RN: 76-99-3
UNII: UC6VBE7V1Z
InChIKey: USSIQXCVUWKGNF-UHFFFAOYSA-N

Note

  • 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. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3)

Molecular Formula

  • C21-H27-N-O

Molecular Weight

  • 309.4503
 

Classification Codes

Classification Codes

  • Analgesics
  • Analgesics, Opioid
  • Antitussive Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Narcotics
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Respiratory System Agents
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule II

Names and Synonyms

Name of Substance

  • Methadone
  • Methadone [INN:BAN]

MeSH Heading

  • Methadone

Synonyms

  • (+-)-Methadone
  • 3-14-00-00279 (Beilstein Handbook Reference)
  • 6-Dimethylamino-4,4-diphenyl-3-heptanone
  • A 4624
  • Adanon
  • Algovetin
  • Amidon
  • Amidone
  • AN 148
  • BRN 3213669
  • Diaminon
  • dl-Methadone
  • Dolophin
  • Dolophine
  • EINECS 200-996-9
  • Eptadone
  • Heptadone
  • Heptanon
  • Heptanon (pharmaceutical)
  • Hoechst 10820
  • HSDB 3119
  • K 174
  • Ketalgin
  • Metadona
  • Metadona [INN-Spanish]
  • Metadona [Spanish]
  • Metadone
  • Metadone [DCIT]
  • Methadon
  • Methadona
  • Methadona [Spanish]
  • Methadone
  • Methadonum
  • Methadonum [INN-Latin]
  • Methadonum [Latin]
  • Phenadone
  • Physeptone
  • Polamivet
  • Racemic methadone
  • Sedo-Rapide
  • UNII-UC6VBE7V1Z

Systematic Names

  • 3-Heptanone, 6-(dimethylamino)-4,4-diphenyl-
  • Methadone

Superlist Names

  • DEA No. 9250
  • Methadone

Registry Numbers

CAS Registry Number

  • 76-99-3

FDA UNII

  • UC6VBE7V1Z

Other Registry Number

  • 297-88-1

Related Registry Number

  • 1095-90-5 (hydrochloride)

System Generated Number

  • 0000076993

Structure Descriptors

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

InChIKey

USSIQXCVUWKGNF-UHFFFAOYSA-N

Smiles

CCC(=O)C(CC(C)N(C)C)(c1ccccc1)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 1538ug/kg (1.538mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Clinical Toxicology. Vol. 6, Pg. 175, 1973.
dog LDLo intravenous 26mg/kg (26mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 157, 1973.
human TDLo oral 1560ug/kg (1.56mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Clinical Toxicology. Vol. 6, Pg. 175, 1973.
infant LDLo oral 1313ug/kg (1.313mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
American Journal of Emergency Medicine. Vol. 6, Pg. 511, 1988.
infant TDLo oral 2mg/kg (2mg/kg) BEHAVIORAL: COMA Clinical Toxicology. Vol. 6, Pg. 175, 1973.
man TDLo intravenous 571ug/kg/5H-I (0.571mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 11, Pg. 346, 1952.
mouse LD50 intraperitoneal 35mg/kg (35mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
mouse LD50 intravenous 20mg/kg (20mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: STIFFNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 163, 1950.
mouse LD50 oral 70mg/kg (70mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
mouse LD50 subcutaneous 35mg/kg (35mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
rat LD50 intraperitoneal 18mg/kg (18mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 47, Pg. 323, 1958.
rat LD50 intravenous 11mg/kg (11mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 25, Pg. 929, 1973.
rat LD50 oral 86mg/kg (86mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969.
rat LD50 subcutaneous 30mg/kg (30mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 238, 1953.
rat LD50 unreported 28mg/kg (28mg/kg) BEHAVIORAL: ANALGESIA Pharmacological Research Communications. Vol. 5, Pg. 175, 1973.
rat LDLo intraspinal 2mg/kg (2mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANALGESIA
Acta Pharmacologica et Toxicologica. Vol. 56, Pg. 50, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.94 (none) 25 EXP
log P (octanol-water) 3.93 (none)   EXP
Water Solubility 48.5 mg/L 25 EST
Vapor Pressure 1.12E-06 mm Hg 25 EST
Henry's Law Constant 4.97E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.05E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.