7-PET

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 checkY
  • Key:CSZMZMPPNJFGRW-TZBHJBKBSA-N checkY
 ☒NcheckY (what is this?)  (verify)

7-PET was discovered by K.W. Bentley[1] and is a potent opioid analgesic drug, 300 times the potency of morphine by weight.[2] It is related to the more well-known oripavine derivative opioid etorphine, which is used as a very potent veterinary painkiller and anesthetic medication, used primarily 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 2200x morphine, almost the same potency as etorphine as a μ agonist,[3][4] and unexpectedly the 3-desoxy compound is also around the same potency of 2000x morphine.[5]

Unlike etorphine however, 7-PET is not an illegal drug, and 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. 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.
  2. 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.
  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 Offline. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.