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Substance Name: Buprenorphine hydrochloride [USAN:USP:JAN]
RN: 53152-21-9
UNII: 56W8MW3EN1
InChIKey: UAIXRPCCYXNJMQ-RZIPZOSSSA-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.Cl-H

Molecular Weight

  • 504.1068
 

Classification Codes

  • Analgesic
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Buprenorphine hydrochloride [USAN:USP:JAN]

Synonyms

  • 21-Cyclopropyl-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine hydrochloride
  • Belbuca
  • Buprenex
  • Buprenorphine HCl
  • Buprenorphine hydrochloride
  • CL 112,302
  • CL 112302
  • EINECS 258-396-8
  • Finibron
  • MR 56
  • NIH 8805
  • RX 6029-M
  • RX 6029-M HCl
  • Subutex
  • Temgesic
  • UM 952
  • UNII-56W8MW3EN1

Systematic Names

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

Superlist Names

  • Buprenex
  • DEA No. 9064

Registry Numbers

CAS Registry Number

  • 53152-21-9

FDA UNII

  • 56W8MW3EN1

Other Registry Numbers

  • 53187-13-6
  • 55327-62-3
  • 64425-21-4

Related Registry Number

  • 52485-79-7 (Parent)

System Generated Number

  • 0053152219

Molecular Formulas

Molecular Formula

  • C29-H41-N-O4.Cl-H

Molecular Formula Fragments

  • C29-H41-N-O4
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C29H41NO4.ClH/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;1H/t20-,21-,24-,26+,27-,28+,29-;/m1./s1

InChIKey

UAIXRPCCYXNJMQ-RZIPZOSSSA-N

Smiles

Cl.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
dog LD50 intravenous 79mg/kg (79mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 1351, 1984.
mammal (species unspecified) LD50 intravenous 40mg/kg (40mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 1351, 1984.
man TDLo oral 2857ug/kg (2.857mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT
British Medical Journal. Vol. 296, Pg. 214, 1988.
mouse LD50 intramuscular > 600mg/kg (600mg/kg) BEHAVIORAL: ATAXIA

BLOOD: CHANGES IN SPLEEN

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 486, 1982.
mouse LD50 intravenous 72mg/kg (72mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 486, 1982.
mouse LD50 oral 800mg/kg (800mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LIVER: OTHER CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 486, 1982.
mouse LD50 subcutaneous > 1gm/kg (1000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BLOOD: CHANGES IN SPLEEN

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 486, 1982.
rat LD50 intramuscular > 600mg/kg (600mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BLOOD: CHANGES IN SPLEEN

BEHAVIORAL: ATAXIA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 486, 1982.
rat LD50 intravenous 62mg/kg (62mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 486, 1982.
rat LD50 oral > 1gm/kg (1000mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 486, 1982.
rat LD50 subcutaneous > 1gm/kg (1000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: CHANGES IN SPLEEN
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 486, 1982.