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Substance Name: Buprenorphine [INN:BAN:JAN]
RN: 52485-79-7
UNII: 40D3SCR4GZ
InChIKey: RMRJXGBAOAMLHD-IHFGGWKQSA-N

Note

  • A derivative of the opioid alkaloid THEBAINE that is a more potent and longer lasting analgesic than MORPHINE. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.

Molecular Formula

  • C29-H41-N-O4

Molecular Weight

  • 467.6459
 

Classification Codes

Classification Codes

  • Analgesics
  • Analgesics, Opioid
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Human Data
  • Narcotic Antagonists
  • Narcotics
  • Peripheral Nervous System Agents
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule V

Names and Synonyms

Name of Substance

  • Buprenorphine
  • Buprenorphine [INN:BAN:JAN]

MeSH Heading

  • Buprenorphine

Synonyms

  • 17-Cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl-6-methoxy-6,14-endo-ethanomorphinan-3-ol
  • 2-(N-Cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-7alpha-yl)-3,3-dimethyl-2-butanol
  • 21-(Cyclopropyl-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine
  • 6029-M
  • Buprenorfina
  • Buprenorfina [INN-Spanish]
  • Buprenorphine
  • Buprenorphinum
  • Buprenorphinum [INN-Latin]
  • Butrans
  • CAM2038
  • EINECS 257-950-6
  • Probuphenine
  • Probuphine
  • RBP-6000
  • Sublocade
  • Temgesic
  • UNII-40D3SCR4GZ

Systematic Names

  • 6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, (5-alpha,7-alpha-(S))-
  • Buprenorphine

Superlist Names

  • Buprenex
  • Buprenorphine
  • DEA No. 9064
  • Temgesic

Registry Numbers

CAS Registry Number

  • 52485-79-7

FDA UNII

  • 40D3SCR4GZ

Related Registry Number

  • 53152-21-9 (hydrochloride)

System Generated Number

  • 0052485797

Structure Descriptors

InChI

1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29-/m1/s1

InChIKey

RMRJXGBAOAMLHD-IHFGGWKQSA-N

Smiles

CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]4Cc5ccc(O)c6O[C@@H]2[C@]3(CCN4CC7CC7)c56

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 17ug/kg/18H-I (0.017mg/kg) ENDOCRINE: ANTIDIURESIS British Medical Journal. Vol. 286, Pg. 763, 1983.
man TDLo oral 1600ug/kg (1.6mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Acta Clinica Belgica. Supplementum. Vol. 54, Pg. 29, 1999.
mouse LD50 intraperitoneal 90mg/kg (90mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 81, 1979.
mouse LD50 intravenous 24mg/kg (24mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 81, 1979.
mouse LD50 oral 260mg/kg (260mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 81, 1979.
rat LD50 intraperitoneal 197mg/kg (197mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 81, 1979.
rat LD50 intravenous 31mg/kg (31mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 81, 1979.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.31 (none) 25 EXP
log P (octanol-water) 4.98 (none)   EXP
Water Solubility 0.636 mg/L 25 EST
Vapor Pressure 9.27E-14 mm Hg 25 EST
Henry's Law Constant 1.76E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.55E-10 cm3/molecule-sec 25 EST

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