7-PET

7-PET is an opioid analgesic drug that has 300 times the potency of morphine by weight.[1] It was discovered by K.W. Bentley[2] and is related to the more well known oripavine derivative etorphine, which is used as a veterinary painkiller and anesthetic medication for the sedation of large animals such as elephants, giraffes, and rhinos. 7-PET itself has a 3-O-methyl ether which reduces potency, but the 3-OH derivative is around 2200 times more potent than morphine, almost the same potency as etorphine as a μ agonist,[3][4] and unexpectedly the 3-hydrogen compound is also around the same potency of 2000 times morphine.[5]

7-PET
Identifiers
IUPAC name
  • (2R)-2-((4R,7S,7aR,12bS,14R)-7,9-dimethoxy-3-methyl-1,2,3,4,7,7a-hexahydro-7,4a-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-14-yl)-4-phenylbutan-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H39NO4
Molar mass489.656 g·mol−1
3D model (JSmol)
SMILES
  • O[C@](C)(CCc1ccccc1)[C@H]7CC64\C=C/[C@@]7(OC)[C@@H]5Oc2c3c(ccc2OC)C[C@H]6N(CC[C@@]345)C
InChI
  • InChI=1S/C31H39NO4/c1-28(33,13-12-20-8-6-5-7-9-20)23-19-29-14-15-31(23,35-4)27-30(29)16-17-32(2)24(29)18-21-10-11-22(34-3)26(36-27)25(21)30/h5-11,23-24,27,33H,12-19H2,1-4H3/t23?,24-,27?,28?,29-,30+,31-/m1/s1 Y
  • Key:CSZMZMPPNJFGRW-TZBHJBKBSA-N Y
 NY (what is this?)  (verify)

Unlike etorphine, 7-PET is not controlled under the UN drug conventions, but it might still be considered to be a controlled substance analogue of etorphine on the grounds of its related chemical structure in some jurisdictions such as the United States, Canada, Australia, and New Zealand.

See also

References
  1. Lewis JW, Bentley KW, Cowan A (1971). "Narcotic analgesics and antagonists". Annual Review of Pharmacology. 11: 241–70. doi:10.1146/annurev.pa.11.040171.001325. PMID 4948499.
  2. Bentley KW, Hardy DG, Meek B (June 1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. II. Alcohols derived from 6,14-endo-etheno- and 6,14-endo-ethanotetrahydrothebaine". Journal of the American Chemical Society. 89 (13): 3273–80. doi:10.1021/ja00989a031. PMID 6042763.
  3. Feinberg AP, Creese I, Snyder SH (November 1976). "The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists". Proceedings of the National Academy of Sciences of the United States of America. 73 (11): 4215–9. Bibcode:1976PNAS...73.4215F. doi:10.1073/pnas.73.11.4215. PMC 431391. PMID 186791.
  4. Bentley, K. W.; Lewis, J. W. (1973). Kosterlitz, H. W.; Collier, H. O. J.; Villarreal, J. E. (eds.). Agonist and Antagonist Actions of Narcotic Analgesic Drugs. Baltimore: University Park Press. pp. 7–16. ISBN 978-0839107255. LCCN 72012612.
  5. Lewis JW, Readhead MJ (May 1970). "Novel analgetics and molecular rearrangements in the morphine-thebaine group. 18. 3-deoxy-6,14-endo-etheno-6,7,8,14-tetrahydrooripavines". Journal of Medicinal Chemistry. 13 (3): 525–7. doi:10.1021/jm00297a041. PMID 5441135.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.